The Devastating Pep Talk That Sparked a New Beginning for Alan Heymann

And what ended up happening, Matt was actually target practice.

The boss had invited me to join him and a couple of members of his team with a member of my team, so he could take some shots at me and kind of express his frustration for things that he was experiencing in his world related to my world.

And it was very odd because it was not an experience I had ever had before, since it was very pointed questions about, why didn't you go to this meeting or talk to that person?

And isn't it true that this thing you said you would do, you didn't really do?

And at one point, he was actually insinuating that I was more loyal to my prior boss than I was to him and saying that he wouldn't be surprised if I relayed the contents of this entire conversation we were having to my prior boss, because this was a fellow who came in and was almost deliberately erasing the legacy of the prior incumbent and wanting to make his own mark.

It wasn't as though you could build on the success of your predecessor.

You had to kind of, like, destroy it to make your own.

And it was odd.

It was ugly, it was uncomfortable.

And the worst part about it was there were witnesses, because it wasn't this one on one conversation that I could go back and kind of process and figure out what to do with.

It was like, in front of an audience, including people who didn't really have any touch with my business function at all, but they were just there as kind of part of the entourage.

Today's guest is Alan Heyman.

He is an executive coach who guides introverts and individuals, navigating really significant life changes.

In this episode, Alan talks about a transformation, formative moment in his career where meeting with a new boss turned out to be really a verbal attack in front of a bunch of other people.

This unexpected, quote, unquote, leadership moment led him to reevaluate his professional path.

We talk about this pivotal moment when he realized that his work no longer aligned with his values and the decision to embark on a new journey.

As an entrepreneur and executive coach.

Alan's story is a testament to the power of introspection and really, truly the courage required to embrace change.

Whether contemplating your career shift or seeking inspiration to align your work with your passions, I think elements of Alan's story will resonate and hopefully inspire you.

So get ready to be inspired by Alan Heyman's journey from this traditional career path to a fulfilling role that truly resonates with his personal aspirations.

Without further ado, here is my conversation with Alan Heyman.

I'm Matt Gilhooly, and this is the the life shift.

Candid conversations about the pivotal moments that have changed lives forever.

Hello, my friends.

Welcome to the Life Shift podcast.

I am here with Alan.

Hello, Alan.

How you doing, Matt?

You know, the secret's out, everyone.

We've been talking for a couple minutes, so we already did these little pleasantries, but that's just how the podcasting game goes.

You know, it's great to have you as part of the life shift podcast.

This.

I think this is close to episode 150, which is kind of unreal to me.

This podcast started as a school assignment during the pandemic.

I was getting a second master's degree because I was kind of bored, and I just didn't know what to do with my time.

And I took a podcasting class, and I was like, hmm, I'll try it out.

I'll see what goes.

And here I am a couple years later, doing this podcast that I never knew that I needed for anyone.

That's new to listening because Alan is on.

The concept of the show started because when I was eight, my mom was killed in a motorcycle accident, and my parents were divorced, and they lived thousands of miles apart.

And I lived with my mom.

And from the moment my dad had to sit down and tell me that my mom had died, my life shifted completely from the track that it was on to a brand new track.

And this was late eighties, early nineties.

And the people around me really didn't have the tools.

We weren't talking about mental health.

We weren't really talking about how to help a child grieve.

And so I pretended everything was fine for decades because I thought that was what I was supposed to do.

But all the while, I really thought, I wonder if other people have these, like, line in the sand kind of moments that just change everything.

And, you know, I'm older now, so I realize that people do, and they have lots of them, and we have these moments in our lives that we can look back and go, wow, had I not done that or had that not happened, what would my life be?

And so I've just been so fortunate to talk to 150 people to hear about these moments in their lives.

And before we started talking today, Alan recording, I should say, you were like, yeah, I've had multiple life shift moments, and it's like that.

Aren't we so lucky to have these moments that change us in ways that hopefully we can reflect on and see as a positive experience down the road?

So, thank you.

Thank you all right.

Let's get started.

So maybe before you get into your story, maybe you can tell us a little bit about who Alan is in 2024.

Like, what's your life like these days?

Yeah, well, in 2024, I'm a husband, I'm a dad, I'm a small business owner, and I'm a member of this tremendous community of executive coaches and facilitators that I've gotten to know through running my business for the last four and a half, five years.

It's a collection of great folks from all around the world, and I feel so fortunate to be part of that group while also charting my own independent way in employment for the first time since I became an adulthood.

So you're not busy at all, is what you're saying.

I would say life is never dull.

How about that?

That's good.

I mean, I think for some people that is a really great thing because it keeps you energized.

And I would imagine that a lot of your story brought you to this point, and maybe it's a welcome time in your life.

I think so.

And maybe just to draw that distinction between busyness for its own sake, and we have a culture of busy in the United States and the western world and doing work that energizes us and motivates us and gives us a sense of purpose, which is what I think we all want.

And I'm feeling very fortunate to have.

And, you know, I think a lot of us want that.

I think society for a long time, and I don't know how it is now.

I'm not as young as I was a couple decades ago, but I felt like for me specifically in that regard, I think society taught me, like, there was this checklist of things that I had to do, and a lot of that came with that.

Busyness came with that you have to graduate high school, then you have to go to college, then you have to get x grades, and then you have to get a job, and then you got to get promoted.

And it was always like chasing, chasing, chasing, very busy life was telling me what I was supposed to do.

I don't know who ever gave me that checklist, but I always felt like I absorbed that.

And a lot of people I've talked to have also had that.

So your distinction really hits in the place of we all wish we could be doing the things that light us up, and sometimes it takes a little bit to get there, but really glad that you're energized.

Yeah.

And it also depends on who our role models are.

Earlier in life, and I feel like the same as you.

I had various people that I worked for, people in my family, people in the academic space who modeled that kind of work, work, work, go, go, go.

And your worth is your productivity or your output.

And, you know, it probably took me until I was in my forties to figure out how to restore, to figure out how to tend to my physical and mental health in service of all the other things that are important to me in life, but also in service of being able to work more sustainably.

Burnout is a real thing, and I see it every day with my clients, especially in certain sectors of the economy.

And I think we need some more foresight from our leadership in terms of what sustainability at work actually looks like.

So you think it's more related to the role models that people looked up to and not so much like what?

I don't know.

For me, it felt like someone was telling me I had to do all these things.

It wasn't my dad, it wasn't the people around me, but it was like this.

I don't know.

I think of high school, and I'm like, there were four paths that we could all take back in high school.

It wasn't like you could do anything you want to do.

In my world, the one that I lived in, it felt like you had to be a lawyer or you had to be a doctor, or you had to be this or businessman, whatever that means.

You have to do these particular things.

That's so interesting that you see it in that way.

I see it as, like, society was yelling at me to do these things.

I think it's both hustle culture is real, grind culture is real.

And there are certainly plenty of occupations out there where that is the expectation when you're starting right out of the gate, and I was no exception.

I started as a local tv news reporter.

I worked nights.

I worked weekends.

I worked continuous coverage.

So I get it.

And it takes a long time to unwind from that sort of thing and to be okay with the idea of saying, I need rest.

I don't want to work 60, 70, 80 hours a week anymore.

So maybe if I have some direction and certainly quite a bit of privilege, I will take steps to make sure I'm not in that space for the rest of my working life.

Yeah.

I would also say, like, in the nineties and maybe early two thousands, rest was seen as, like, you wouldn't tell people you needed that because it was like a vulnerability.

Like, you were weak.

You couldn't, you know, so I think it's nice that people are now leaning into this, like, self care, self awareness.

It's okay to not be okay.

Like, all these mantras that people are adopting in a way that kind of allow us to find that rest or to find that safe space.

Absolutely.

And it helps me work with my clients because they know there's a need and they're comfortable more and more discussing it.

And what you do for them is probably helping them also, or reemphasize the ideas that, you know, where they are is okay because other people have been there, but there's also a way out, and you can be okay in this other space and feel a lot more energized, like you were talking earlier.

So fascinating.

Sorry, we went off on that tangent.

But, you know, I think it's important to say because I think so many people kind of just adopted these ways without really thinking about it.

And now I think some of us are kind of waking up to that.

And like you said, in your forties.

In my forties, I'm like, oh, I can do what I want.

That's cool.

So, yeah.

Or I can do less of what I don't want.

Well, that's true, too.

Unless.

Yeah, yeah.

There's also little, like, little notes here and there where it's like, well, some things you're gonna have to do, but that's okay.

And that's part, just as a human part of life, as an adult.

Right, exactly.

So maybe you can kind of paint the picture of, of your life leading up to this moment that ended up creating this version of Alan in the world.

So go back, however you.

However far you need to, to kind of paint this picture.

Absolutely.

So I've had several careers during my adult life since graduating from college, starting, as I mentioned, with a local tv news reporting job.

I went to journalism school and for a while had the fantasy slash ambition, I would say, of being the next iteration of Peter Jennings or one of the great giants of television from when I was growing up.

Didn't work out that way, as it doesn't for the majority of people who pursue that path.

And that's all right.

I had a number of twists and turns that got me to the pivotal point that we were preparing to discuss today.

But the long and the short of it was I was working in several different roles and in several different organizations.

For somebody who I knew and trusted very well, you know, once in a while, we have the good fortune to find ourselves in the company of a boss that will follow from organization to organization.

Or role to role.

And that had been the case for me, and I was in my third iteration of that.

And it was wonderful.

It felt like home professionally, and there was trust, there was safety.

There was go ahead and take risks and try new things, and if it doesn't work out, we'll support you because it's kind of for the good of the order.

What ended up happening, though, is that the boss left the organization.

And so that is going to create a fair amount of uncertainty in anybody's world, in any organization in mine, because I was a direct report to the head of the organization, because I was in kind of a new and somewhat untested area of the.

There was a vulnerability there, depending on who was going to take over.

And what ended up happening after an interim period of being led by somebody who I also knew and trusted, was that there was a leadership change at the top of the organization.

And my boss was a stranger, probably for the first time in more than a decade, because I had always worked into jobs through connections that I had in organizations where I already had contacts.

That's a common story, at least among my clients, is that you don't necessarily get your job by applying to a bunch of postings on LinkedIn.

You find somebody who knows somebody, you make your way in.

So I was working for a stranger, and there's a getting to know process that happens in that kind of a dynamic.

And I have to say that the early signs did not feel very encouraging to me, but there were no alarm bells.

And when I say this, I say it in the most kind of gentle, charitable way possible, in the sense that not everybody is going to be a match for every person that they're working for.

There are style differences, there are experience differences, there are identity differences.

And to me, that's part of work life.

It's not human tragedy.

It's just there's not always a great fit.

And I started to get a sense that it was not going to be a great fit, but I didn't know exactly, and I was going to give it some time to just kind of work itself out.

And I think, uniquely, you had also that safety for a decade, too, which kind of lowers all of our guards a little bit, too.

So you have a new body coming in here to kind of navigate.

And I guess you said, like, with kindness, you say that, that it wasn't big alarm bells weren't going off, not just yet.

It wasn't going to be like before.

It was not that I knew.

And one of the first things that I began to notice was that there was an issue with access in that, you know, going back to the old Hamilton line, I tended to be in the room where it happened before under the previous administration.

I was being excluded from meetings.

I was being left out of conversations.

I was nothing.

Knowing what was going on at the heart of the organization.

And when I needed access for guidance or for a decision that I couldn't make on my own or for allocation of resources, I couldn't get it.

It was hard to reach the guy.

We were in different buildings.

We didn't meet that often, so there wasn't a lot of contact to base rapport and relationship on in the first place.

And I wasn't getting the kind of access and exposure that I felt were necessary for me to be successful.

And I dont want to make it sound as though I was some sort of needy special snowflake or something along those lines.

I was judicious in knowing that the people that I worked for were busy and I wasnt going to demand their attention where I felt like I didnt need it.

And certainly theres plenty of jobs where you dont run into the boss hardly at all, and you can be successful.

Look at the federal cabinet in the United States government, for an example.

You do your thing.

I tried to do my thing, but there were times where I needed something and I couldn't get it.

And what happened was, we were based in DC and the DC area.

There was travel to a conference representing the sector of the economy that we were in for our organization.

And I took a member of my staff there, and there were a number of colleagues around.

And I did the conference thing and I ran into people from other similar organizations around the country, and I said hello, and how are you doing?

And we caught up and I caught some great presentations, got some inspiration on the very last day of the conference when I was basically almost checked out and just ready to go back to work mode and get home after a bunch of days.

I got invited to meet with my boss and I got invited to meet with my boss at the last minute without much clarity on what the meeting was, which is always kind of a little bit of anxiety inducing when you don't know a person well.

And it turns out what happened was this meeting was in the not yet open hotel restaurant, so its deserted, its tables with chairs folded upside down on them and that sort of thing, if you could picture it.

And at that conversation was not just the boss and me, but it was a couple of members of his team.

And I had brought along a member of my team as well.

So it was almost like kind of like a summit in a way.

And I had no idea how to prepare for this experience or what was going to be needed of me, what questions would be asked.

And usually I like to go in with a bit of a, so im not wasting peoples time.

And what ended up happening, Matt, was actually target practice.

So the boss had invited me to join him and a couple of members of his team with a member of my team so he could take some shots at me and kind of express his frustration for things that he was experiencing in his world related to my world.

And it was very odd because it was not an experience I had ever had before, since it was very pointed questions about, why didn't you go to this meeting or talk to that person?

And isn't it true that this thing you said you would do, you didn't really do?

And at one point, he was actually insinuating that I was more loyal to my prior boss than I was to him and saying that he wouldn't be surprised if I relayed the contents of this entire conversation we were having to my prior boss, because this was a fellow who came in and was almost deliberately erasing the legacy of the prior incumbent and wanting to make his own mark.

It wasn't as though you could build on the success of your predecessor.

You had to kind of, like, destroy it to make your own.

And it was odd.

It was ugly, it was uncomfortable.

And the worst part about it was there were witnesses, because it wasn't this one on one conversation that I could go back and process and figure out what to do with.

It was like, in front of an audience, including people who didn't really have any touch with my business function at all.

But they were just there as part of the entourage.

So what didn't I do?

I didn't have the courage at that moment to say, what is this?

What are you doing here?

Or to just stand up and walk away and say, I don't, you know, I don't need this crap.

I'm out of here.

I just sat there, and I kind of took it.

I answered a few questions.

I kind of realized my role in this conversation was just to kind of take the hits, not to actually provide information or rebut after.

That probably wasn't even about you.

Exactly.

And I can't tell you how long it actually lasted.

It felt very long.

But I went to the bar afterwards and huddled with my colleague from my team, and she was pretty devastated, and she was almost in tears, and she said, you know this is really bad, right?

I said, yeah, I know this is really bad.

I don't have words to protect us or chart the path forward for us based on what just happened.

I need to process it a little while.

But, yeah, I agree with you, it's pretty bad.

So meeting over conversation, debrief with my colleague in the bar over afterwards, I think she went out and did a little bit more processing of her own after the fact.

And that was the moment in which I decided, okay, I don't know when, I don't know exactly how, but I'm going to leave this job and start my own coaching business, and it's going to be sooner rather than later.

Because you wanted to have no one else be in that situation before.

Was that kind of the impetus of that?

Yeah, it's a couple of different things.

With the coaching element, I should tell.

You that the coaching piece had become less and less of my portfolio within the job.

So in addition to any kind of friction or frustration with the boss in that relationship, like, the subject matter of the work I was doing was getting progressively less and less interesting.

And then we had this flashpoint in the hotel bar in Nashville at the end of the conference where I'm like, okay, so my job here is apparently just to absorb the frustrations of the chief executive rather than actually do something productive or something that feels good to me.

And that was the moment that after almost 25 years of having been somebody else's employee throughout my entire career, that I kind of got over having a boss.

Yeah.

Cause you don't want to be in that situation before.

I mean, from you telling that story, I think, like, as this grown adult now, I'm like, that was nothing about you.

It seems like he was just trying to show off and show power with his insecurity in front of other people.

I mean, you don't have those conversations with people in that way, but I can't imagine being in your situation because it's like, what do you do?

Like, I know you said this is what I didn't do, but, like, are you even supposed to do that?

Like, we're.

These are not things that we're taught to experience, nor should we have to.

So, you know, I think, like, what would I do in that situation?

I probably feel really defeated.

Yeah.

And I did.

And I don't necessarily, you know, I say all the things that I didn't do and could have done.

Obviously, in hindsight of many years, I don't think my response or my lack of response was the wrong call at the time, but it was very middle school playground.

And what I came to learn about this person and the way that he led was, yes, as you say, it was power over.

And sometimes he would respond well to if he throws a punch, if somebody else hits back, which is good to know in hindsight.

It's also nothing.

All my style as a leader or as an employee.

And so what that tells me is that I don't have what it takes to kind of be successful in that environment.

And again, that's my very neutral way of saying that, because it doesn't, you know, cast judgment on either party.

It's just like, okay, this is the leadership dynamic within the organization.

This is a dynamic that makes me uncomfortable, that doesn't fit well with who I am, therefore Sia.

And it was far different than what you had experienced for the decade prior, right?

100% different.

And, you know, these things do happen.

And as I said, bosses change.

And sometimes your moment of knowing that this is not a good fit is not as focused or as dramatic as mine was.

But, you know, it's almost as though I had been kind of waiting for a sign for a little while.

And, you know, it doesn't get any clearer than that.

No, not at all.

And you hadn't heard, like other people say, like, their experiences with him or anything like that?

Oh, yeah.

Okay.

You know, and that, you know, what I can share is that people I was close to were not treated kindly on their way out, whether it was their decision to leave or whether the decision was made for them.

And there was a lot of turnover, there was a lot of turmoil.

There was a lot of fear in the environment.

And I think that was kind of by design, and that's not the way that I like to lead.

And I think that the good news is, one, that I was able to turn the corner and establish my own business and be successful, not have to talk to this guy ever again in my life.

And two, is when I do have clients who are working their way through what I would call a toxic leadership environment, I know how to recognize the signs.

I know what it's like to go through that experience and to kind of walk along with them as they figure out what the proper path is supposed to be.

So when you left that conference, was it a lot of soul searching of, like, how do I get out?

Or did you already kind of start.

Had you already started building a little bit of an idea or a plan to move forward?

Because you said things were getting kind of not exciting, not, I think it was built.

So what I had been doing for a little while was I was coaching on the side.

Im East Coast.

I would coach some clients on the west coast after I got home in the evening, take some PTO, take some lunchtime.

So what I at least had was proof of concept that this was something I could do and get paid for.

That makes sense.

Was fortunate to build up some savings so that there was a bit of a cash cushion, especially once I made the decision, but before I made the jump.

And so for me, it was more like, okay, let's make a plan.

Let's have a timeline, let's execute on this thing.

And that has always been something that comes rather naturally to me, as in, let's take some time and gather some inspiration and check in with some people on the decision itself.

But once the decision is made, I will come up with a plan and I will get us there.

We'll decide, my family and I, that we're going to go to Seattle for four days in August for vacation.

And that decision is what I need to kind of build the plan from there.

So that's what I did.

And it was careful, it was quiet.

I did not talk to a lot of people about what I was doing.

And I said, okay, this is now February, that this incident is happening in Nashville.

I want my quit date to be Friday, November 1.

And that's what it was.

That's very specific.

Yeah.

And there were different things operating in terms of school year and vesting of retirement plans and various things like, so that's not important.

But the target was November 1, and I kind of, like, put the steps in motion backwards to make it happen.

I like that.

A planner, the planning is an important aspect, and it's not always great to just jump.

But I'm wondering how you show up.

How do you show up as a good employee after a situation like that?

In that interim, how do you do it?

Yeah, it's tricky.

And I think my past experience is kind of like a recovering diplomatic people pleaser.

Comes in handy in a situation like that, and then I'm not going to be unpleasant to people.

I'm not going to be throwing bombs in my wake or just kind of try to blow the place up on my way out.

I was the founding head of this particular business unit that I was leading, so there was important work to be done in getting the transition ready, and I really did want it to continue succeeding after I left.

So I didn't bear any ill will toward my colleagues, my staff, the actual organization itself.

It was just, I knew I wasn't getting along well with the head.

And so there was succession planning.

There was a fairly long period of time there where I knew I was going to leave and nobody else did because I needed to kind of keep it to myself to keep the plan going, to get the clients to have in that was a little bit anxiety inducing because there were people who I knew and trusted in the organization who announced their plans to leave, it turns out, too early, and were basically told, heres your cardboard box, youre done now.

And I didnt want that to happen because I wasnt ready financially, mentally, etcetera.

So it was a lot of quiet, behind the scenes work, almost in two directions.

One future of the business going to continue without me into this new thing that not a lot of people are going to know about.

And it was headache inducing at times, a little bit stressful to kind of be in both places in your head at the same time.

But I've done it before in the sense that I'm about to leave a job for a new job that I've accepted that people don't know about back here, it was just a longer incubation period, and it was my own thing that I was starting that was deeply tied to my identity as a professor professional, rather than just signing on the dotted line to take another job someplace.

Right?

Yeah.

Cause I was gonna ask if it was, like, really draining to have to show up in a, I guess, diplomatic way.

Cause I could imagine, like, you can't fully be yourself because you're, like, scary.

That guy's scary there.

But then you also have this exciting part.

So, like, I wonder if there was like, this balance of, like, oh, well, that one's sucking all the energy, but this one's giving me all the energy.

Yes, I think that was absolutely true.

And I think that what I would describe in hindsight is escalating levels of relief from struggle.

And so the height of the struggle was in the moment where I was basically being dressed down in front of an audience.

But the relief that came afterwards was almost instantaneous, and it was monumental to the point where I think if you asked her now, my colleague, who I went to the bar with afterwards, who witnessed me taking all these shots, would have been concerned about how not bothered I seemed at that moment when she had been through exactly the same with me, near tears, wondering, what's going on?

How do we make sense of this?

I had immediate clarity, and I felt really good in that moment about the fact that this was it and I had decided to leave, you're like, thank you.

I didn't say it to my colleague or anybody else.

And so the source of that relief would not have been obvious.

So for the interim period, there was that very tangible, very instant relief, along with all of what you just described.

And then when, of course, I left November 1, then it was all of the relief.

It was light as air.

Did you get to tell him that you were leaving?

I did.

I did.

And it was an awkward, uncomfortable conversation.

And expect that, right.

There were not actually many one on one conversations between the big sort of dressing down sporting event, whatever, and the resignation moment.

I gave about a month's notice, and he was not expecting it at the time that it happened, but it was one of those things where when you're a leader, you have a responsibility to understand and to internalize the impact that you have on people through your words and actions.

And what this was was I had a meeting scheduled with him, one on one, that was dropped onto my calendar by his assistant with no subject line and no information for late in the afternoon toward the end of the week.

And so I walked into this meeting prepared to resign from my job, not knowing if I was also going to get fired.

And at that point, of course, it didn't matter, but it was still a little bit like nerve wracking and all of that.

And the thing is, the conversation we had was perfectly pleasant.

It was probably the most pleasant conversation we had ever ended up happening.

And he conducted himself exactly in the way that I would have expected somebody who has this type of conversation on a fairly regular basis would do.

It was pleasant.

He listened.

He understood.

He shared a few things.

He expressed, actually, a little bit of disappointment, which I dont know if it was sincere, but it was shocking to me.

This was toward the end of the week.

The following week, his assistant called me and said, so, are you going to give us a letter?

Sure, ill write a letter, no problem.

So I wrote the letter.

I went upstairs, I handed it in, and I went to a meeting or something.

And I came back from the meeting, and the member of my staff who had been with me in Nashville looked at me and said, have you checked your email recently?

And I said, no, I was in meeting.

She said, check your email.

The boss had sent an organization wide announcement that I was leaving while I was in the meeting, after I turned him, so he scooped me on my own nuke.

Yeah.

Power.

Yeah, exactly.

So that was it.

I was there for a pretty easy month afterwards, doing transition, handing stuff over to my successor.

November 1, I was out, but it was like there had not been any doubt about my decision in that moment at all.

But if there had, there's another sign for you.

Yeah, there's a couple thank yous that come along with, like, thank you for doing what you did, even though it was terrible.

Yeah.

And also thank you for just doing that, because you just confirmed that all my decisions are.

Are the right ones.

I wonder if he even remembers the conference moment.

Probably not.

It sounds like he was like that.

I would be surprised just because he remembered.

Yeah, it seems like that kind of thing was a bit of his style.

All of the people who were involved in the conversation, other than him, are no longer in the organization, so there wouldn't even be anybody to lean on in terms of a memory of that.

Yeah.

It's so interesting.

I think there's a lot of people like that, and they don't.

Like, somehow they.

Maybe they do, but it seems like they don't realize that maybe they're the common denominator to a lot of these situations.

And I.

You know, I was gonna say, I wonder if you work with people like that, but they wouldn't be aware enough to reach out to you for coaching help, so probably not helping those types of people.

It depends.

It depends.

And sometimes you don't reach out and.

Be like, I hear you're terrible.

Would you like to be?

There may be a board member or an executive committee or some sort of entity like that makes a gentle suggestion.

I don't know.

I'm somewhat skeptical of the idea of coaching as a remedial practice of coaching as a place where you send someone to get fixed for something.

However, I will say this.

I think my background as an employee and as a coach very much led to the clarity that I experienced in the moment that I had in Nashville.

And I can imagine very much having a client that I'm either working with already or somebody new comes in, trying to process through a moment like that and figure out exactly what it means and find the right framing to make it actually helpful, as you've described, to turn it from this, like, crisis into the.

Thank you.

I feel like they're just like.

Just like with therapy, I think coaching, like, someone needs to have enough self awareness that and, like, onus on the things that they do to be able to make those things.

This is just me assuming that to make those things changeable or doable or, I think, like, therapy.

I didn't go until I was in my thirties, because I wasn't ready, like.

And then when I was ready, it was like the clouds parted and all the things happened and, you know, but I knew if I had gone in my twenties when I was pushing everything and blaming everything and all those extra things, I don't know that it would have sunk in.

So I think coach, I think of coaching very similarly.

I think in the sense that both of them start with a desire for change on the part of the participant, then, yes, 100% the remedial part.

I feel like they would just check a box and then maybe go back to their old.

And this used to be the thing.

This used to be almost the pity move as the person was gently nudged out the door.

We'll try to set them up with a coach and see if they can salvage something before outplacement happens.

Not very effective, in my view.

And so I'm glad that we're not focused this way.

And I've been fortunate to work with a number of quite young emerging leaders in this practice, and getting to them at that moment when they're first developing as the leader and everything is wide open and they haven't even nailed down their own style yet is amazing because they can have such impact.

Do you look at that moment as anything in you changed?

Or was it like you had this slow fire burning and then that was the oxygen it needed to light?

I think that was it.

I think it was an accelerant on something that was already kind of smoldering rather than a big change pivot kind of within me, because there wasn't, I couldn't say.

And that was when I discovered I was an entrepreneur.

No, it was just that I discovered that the timing for a bunch of things I had been wondering about or wishing to explore was now rather than later.

Did you have the confidence before that you could run your own business or was this like, well, let's try, because this sucks kind of moment for you?

I think I would answer the question in a couple of different ways.

So I had been a partner in a very small business in my early twenties, and I had started this sort of business within a business that I was actually working in at the time that this terrible conversation happened.

So I guess what Im saying is, in terms of the mechanics of launching an entity, of bringing a corporate body into being and systems and processes, yeah, 100% totally fine.

And I dont want to overlook that because a number of people in my line of work dont have the skills or the confidence or the they need to outsource it or get on top of it right away.

That was not the issue for me.

The issue was, can I make a living at this?

And fortunately, at least early on, it was not, can I replace my existing full time, every other week salary with this, but can I make a living at it?

What I needed for that was really two things, proof of concept and savings.

And I had been accumulating both.

And one of the reasons why it took from February to November for me to leave was also the savings piece to be able to give myself enough Runway so that if this thing didn't take off quite the way that I thought it was going to or hoped that it was going to, we would still be okay.

Like a pragmatic, practical jumper.

Well, yeah.

And to this day, I wrote a blog post just this last week about how in the month of July of 2024, which is now almost five years into my business, I made $600 like gross revenue, which is less than I would have made if I was working a week at minimum wage in the jurisdiction where I live.

It happens.

Theres a lot of up and down in self employment and were fine.

And I saw it coming and I knew why it happened.

And its all good.

But I would not have had the confidence at that moment, right after that meeting in February in Nashville of 2019 to be able to say, guess what, Alan, of the future, youre going to make $600 at some .4 and a half years from now, and youre going to just still be loving life.

Trey no, I said that in a way that its great that you have the ability to plan and think ahead and think through all the options, because I think theres also a bucket of entrepreneurs that are so passion driven that the rules and the roads and the things dont matter because theyre going to jump fully.

And its like you have this succession plan for yourself, like, of how you were going to move through this space.

And he just, like you said, through some, you know, lighter fluid on the, on the fire that you had, because you had the proof of concept, you had a process, probably, of how you were going to do things.

You had the experience running the other businesses.

So it's like a really a nice blend of what probably a lot of entrepreneurs that are kind of winging it would love to have in their experiences.

I appreciate that.

I think it truly is a balance.

And I'm fortunate to be connected with a lot of entrepreneurs in my space who have great vision, who have great purpose, who have great ability to inspire, which I need more of in my own personal mix, because I'm methodical, I'm risk averse, I'm cautious at times in a way that is comfortable, in a way that is safe, but a way maybe that doesn't stretch my boundaries the way that I could.

And I've had the good fortune to work for a good number of leaders as an employee where that was their strength.

They could pull the best out of their people through that inspiration.

And it's something that I miss sometimes now that I'm working for myself.

So being connected with others kind of helps scratch the itch there a little bit.

Trey, what have you learned from coaching all of these people like about yourself?

What is this new journey in your life been like for you in your growth period?

I think I could point to a few things, one being the struggles that I experienced as a leader within organizations are not unique to me in the sense that my clients are often bringing them in.

And I think part of that is because there's almost a universal nature to leadership.

And part of it is that I think my clients tend to meet a similar profile, and sometimes that profile is similar to me.

And there's a nice kind of reassurance in that that I may not have known it at the time, but I was not alone in what I was experiencing.

Two, ive been very, very lucky to take careful note of my preferences in energy levels and capabilities and to know what I can deliver effectively and when I can be in service of my clients and when I cant.

So one of the things I think we all fall into as entrepreneurs is we just take, say, our target dollar figure for the year or past salary, whatever that is, and back it into the number of possible working hours in a year.

And the thing is, much as I'm imagining, you can't record five or six podcast episodes in a day, every day for a whole week, and then do that for a year.

I have a limit on how many coaching sessions I can deliver in a week, or how many facilitations I can do in a month before my energy level is compromised and the quality of the work starts to suffer.

And I've learned that a little bit through trial and error and a little bit through experimentation, and too much.

And too little.

But it's a great thing to know, because then I can decide how much do I need to do to make this thing work for me, for my clients, for my family?

And I did go into this with at least the idea that I would try to be working a bit less than when I was full time working for others and commuting back and forth into an office every day, because remember, that was pre Covid and I've met that milestone.

So I'm not putting in the hours that I did in past jobs.

I'm thankful for that, and I probably could do that if I wanted to, but being in service to the people that my practice supports and to my family is the priority, and I can't do that beyond that kind of threshold of diminishing returns, right?

No, I think that's super important, especially for entrepreneurs to hear that you still have to create, you actually have to create that balance, you have to create that awareness, you have to create that space so that this is business, this is life, and you have to find that balance.

I think a lot of people, like you said, just dive right into it, try to do it, but also on the same thing.

And I wonder if this is true for you.

Are there certain people that you just won't work with if they want your service, but you find out a little bit more about them and it's like, that's not a right fit and you're okay saying no.

Is this something that you do?

It seems like yes, but yes, that.

Is definitely something that I do.

Not often, because I think whatever it is that passes for my client attraction process these days, and it's pretty loosely defined, tends to bring in people who I'm interested in working with.

That's fair.

I work as a contractor to a number of different coaching service companies, and the ones that I'm working with now are very skilled at bringing together coaching clients.

So they'll put myself and two other colleagues in front of someone and let them choose.

And it would have been a great fit for all three of them kind of thing.

But it does happen, and I have gotten quite comfortable over the time that I've been doing this business at letting folks know, hey, this is not my sweet spot, I'm not skilled in this area.

Or there's something about your profile, it's not a great fit, or we're having an introductory conversation and there just isn't the chemistry.

Very, very happy to refer a person like that out to somebody else in my ample network of fellow coaches who do things slightly differently or do slightly different things than I do.

Sometimes it's timing, sometimes it's pay or the amount of effort that would be required in engagement.

Sometimes it's style.

And I remember very clearly before I even left my position as the full time employee that we've been talking about this evening, I was getting inquiries, and I was having conversations with prospective clients, and it mattered at that point because every session that I booked was a session I would get paid for, which was proof of concept and experience and networking, all that.

I got a call from a friend of a friend who was in pretty dire straits and was looking for a coach to support him in the leadership journey.

He was the number two person in a startup, and I basically said hello.

And he was probably 25 minutes into the call with complaining about how terrible his boss was.

And when he finally paused, I said, hey, I just want to say at this point, I don't think you need a coach.

I think you need a new job.

And he didn't really want to hear that from me, but he heard it.

We didn't have another conversation.

There was no coaching engagement.

I don't know where he went or what he did, but it was this kind of aha moment for me where it's like, wait, I would love to have revenue, I would love to have clients, but I can't help this person where he's at right now in the way that he thinks he needs me to.

And so clarifying that and what coaching is and what it can deliver is important because I want to make sure we're meeting people's expectations.

No, I love that.

I wish a lot of people in certain fields would have that understanding or have that click type moment in which it's like, could I take money from you and could I do this?

Sure.

But am I going to?

No.

Because it's not the right.

You know, like, and that's.

That's the sign of, like, you're doing what you should be doing, and it's the right space for you, and it feels, like, authentic, and it lights you up.

Like you said, it energizes you.

It's.

All these things kind of make sense, and it's not just, like, another job or another thing to do.

It's so.

It's so interesting because before I started this podcast, to be totally honest, I don't think I knew too many coaches.

Like, it feels like there's a lot of coaches out there that it just, like, it just wasn't even in my awareness that people sought anything other than a therapist, you know?

And so.

But there's coaches for everything.

I mean, I guess I knew there were, like, baseball coaches and things like that, but, like, people in the business world and people in certain areas have, you know, all these different coaches, and you said you have a huge network of people.

Are you finding there's a difference in the last, like decade in the way that people seek out or use coaches.

Has that been a shift in some way?

Absolutely.

So there's a growing awareness of coaching, I would say, and I can trace this back to my own origin story in that ten years ago, I hired a coach pretty much as soon as I found out what a coach was and what a coach could do and that I was having some leadership challenges in a different job at a different employer, and an executive colleague of mine was in coaching school, and I didn't even know what that was.

But it mattered to her and it was important and it was interesting.

And I hired one of her classmates, and to this day, she, my former coach and I are still doing work together, so her business has really taken off.

But, yeah, look, Georgetown University, where I got my coaching certificate, is now teaching more cohorts each year than it did when I was in the program six ish years ago.

The International Coaching Federation, which is our member association, is growing by leaps and bounds.

The conferences get bigger every year.

And when I attrive that, too, is that the field has grown and it has also trickled down past the C suite of, let's say, the Fortune 50 or the Fortune 500, because it used to be that only the really, really, really highly paid executives in any given organization could get coached because it was so expensive and it was in person and it was all day and it was very, very high ticket.

And now I coach emerging leaders at nonprofits sometimes, and it's very valuable, interesting, meaningful work.

And the fact that there's more of us out there doing it has almost democratized it in a way.

And you want to be careful because you don't want it to be a race to the bottom.

And there are some providers out there who are doing that in terms of what they charge and what they pay.

But I think there is a lot out there.

And one of my earliest discoveries on becoming a coach, to my great delight, was that we are kind and generous people for the most part, and we're not competitive or we're not out there trying to take each other's business.

And if I'm not the coach for you, my neighbor over here might be.

And I get a lot of business that way, either working with or for fellow coaches or just referrals, because you also get to the point where you've been doing this for a while and you build the network and there's going to be more demand than there is supply.

So it's great to be able to.

Share Trey from your perspective, which will probably be biased because you are a coach, what are some of the benefits for, for someone if they were to get a coach versus whatever else is out there?

A book?

I don't know.

Sure.

No, absolutely.

I appreciate the question.

And that question, almost with the exact same phrasing, came my way as a gift in one of these introductory coaching conversations with a potential client.

That person, by the way, hired another coach, but appreciated the answer.

And so what I did was I on the fly, kind of off the top of my head, broke it down into four key benefits that I tend to provide over and over again with every single engagement that I do.

And other coaches operate differently, but this is kind of my model.

The first and probably the most important is reframing.

And so what is required to change a mindset is to change actions and behaviors.

And to do that, you've got to be able to look at your situation differently.

And the way you look at your situation differently is you talk to somebody who's not in your situation, who doesn't have your coworkers, who exists outside of your leadership bubble and can see things upside down and sideways and say, have you considered this or what about that?

Item number two is curation.

You mentioned it just now.

What about a book?

Well, I've got a ton of books over here.

There's tens of thousands of leadership books on Amazon that you could order.

What are you going to read?

Who's the expert that you're going to find to help you address your issue?

I know who these experts are because I'm a generalist, not an expert, and because I work in the field.

So I read stuff like this every day.

My clients always get videos and podcasts and Ted talks and books on the things that are affecting them.

Item three is accountability.

We're going to develop action plans together that are going to help you make some change in your world.

You're going to talk to those five people.

You're going to approach a conversation a little bit differently.

You're going to put your phone outside the bedroom at night and get an alarm clock, whatever that is.

Imagine that.

Yeah, imagine that.

Right?

I've had clients who've done it.

It's almost magic.

But seeing it in front of me means you're going to be more likely to do it.

It's the same reason that fitness trainers get paid a lot of money.

They hold people to account for the actions they commit themselves to.

And the final thing is what I call the balance between support and challenge.

I am the supporter among supporters for a leader who's in crisis or having a hard time, because leadership is hard.

I've been through it.

If it was easy, we'd have nothing to talk about here.

At the same time, human beings are human beings, and power is power.

And what happens is there's a bubble that gets created around every leader where they're going to be surrounded with people who will tell them things over and over again that they think they want to hear.

It's not because anybody is evil or nefarious or anything like that.

It's just the way that it works.

I am outside the bubble.

So in a supportive and kind and often loving way, I'm going to say the thing that nobody else is going to say, and if you don't like the thing that I'm saying that nobody else is going to say, but maybe it takes you a little while to go back and process it as you're feeling your feelings about what I said.

I get to stay married and keep my house.

And that is a wonderful benefit of being a disinterested third party who doesn't have a statement of the outcome.

I like that.

I like the idea.

It all makes sense.

And it's like, I always look back, I'm like, why didn't I know of this?

And maybe it was that top tier thing where I just wasn't making that kind of money and I just didn't even, it wasn't even in my awareness because I wasn't out there.

But it's so fascinating to hear how many.

And the people, like, I talked to other coaches that are, like, very specific, they only focus on this or they, you know, like, and it's so fascinating that you can find your own space here.

And it's so valuable because, like, I mean, like, we even that, like you said, fitness coach or, like a baseball coach, like, that's just someone that's gonna help them get better at whatever they're doing in their sport.

And, you know, it's the same kind of thing.

So, yes, it's funny that looking at myself and going, why didn't you even know about, you know, like, it's kind of humorous to think about, but I love that you're, you know, you found something, even though you have it before, but you found something that you can do every day, all day long, if you choose to, that energizes you, also probably drains you, because just as having conversations on podcasts can be draining, right.

If you're talking about really tough things or you're, you know, in a really intense moment with one of your clients.

It's probably pretty draining, but it energizes you just the same because you're helping.

You're doing the things that, you know, I think everyone should be doing with each other through conversation, through, like you said, you end up in this bubble, and people are afraid to pop the bubble every once in a while, you know, to make people uncomfortable and push them a little bit harder.

So I love that you found this for yourself.

And it's like you think back to that moment where that guy was just a total a hole.

I said it, you didn't say it, and you almost want to be like, thank you for that, because you kicked this off.

Like, I know I started it, but, like, you really kicked it into high gear because he did that.

Do you look back at that and go, well, I'm glad he did that?

Kind of.

Yeah, I mean, that was his, I'm quite certain, unstrategic, unintentional gift to me.

Right.

Yeah.

And I will tell you, I've had less painful versions of that conversation a couple of times during my career that were more directed, and I actually have a term for it that I use from time to time when I'm talking to a client who.

They have an employee who's just a real challenge, and they wish there would be a change somehow, but they don't know how to move the needle.

The term that I use is devastating pep talk, and it sort of consists of somebody who's in authority going to the other person and saying, hey, I know this has not been an easy time for you.

I know this has been a bit of a struggle.

I know there's been a little bit of a misfit fit, maybe with your interests or maybe with your motivations.

Will you please take the weekend and give some serious thought to your future and figure out whether this is actually what you want to be doing with your life professionally.

And if it's not, let me know what I can do to help.

Anything.

You have my support, you have my connections, whatever you need.

It's risky.

There are some HR things that you have to be aware of if you're initiating a conversation like that.

And of course you're doing it because you wish the answer will be no, and that they'll figure it out and leave on their own, which I've done a couple of times in my career.

But wouldn't it be lovely if we could all just sort of be adults and be more open about this sort of thing and have a conversation and come to a solution that actually works for both people when those interests are no longer aligned.

So in my mind, the sort of the actionable, kinder, gentler, more giving version of the conversation that I had in Nashville in 2019 is just that.

Like, really?

Is this for you still?

Because in his sort of underhanded, target practice, power over kind of way, maybe that's what he's asking, even though he didn't actually use the words.

I'm not convinced of that.

I like the idea of the devastating pep talk, though.

I like the idea of people being open enough to be human with each other and not just boss and employee or whatever leader and.

And underling, whatever we want to call him.

I like the idea of totally being open and saying, hey, this just isn't the fit, and I'm going to move on.

It's nothing.

You did nothing, any of those kind of things.

But the way you told the story, this guy just sounds like he just wanted to show off in some way, and it wasn't really about you.

But I'll just take that for what it is.

No, I think I kind of have the same kind of parallel to the Life shift podcast and thinking, like, what if we all just had these conversations and talked about the things that were hard and we talked about the things that maybe we weren't good at but we'd like to get better at?

Or we said the vulnerable things out loud, and then we realized, oh, you also feel like that, oh, I'm not alone.

Oh, you got through it by doing this.

Cool.

Maybe I'll try.

You know, like, those are the ideas that I have.

I think, of this eight year old version of me.

Had I known other people that were grown up, they had lost their parent, and they were successful and they were happy and they were doing all these things and they had a path forward, maybe I would have been like, oh, there's hope, instead of being whatever I did for 20 years in this grief process.

And so, you know, I love that idea, and I hope we get there of this.

You know, maybe they're not devastating pep talks by them.

They're just talks, you know, and they're just realistic conversations about not the right fit, you know, like, you don't love it, that's okay.

We can move to the next thing you know.

Yeah.

It's not tragic.

It's just kind of part of work life.

And sometimes things are a fit and a connection, and then after a while, they're not for various reasons.

So it does not always end the way that it starts.

That can be said of relationships, that can be said of family members, that can be said of all sorts of things.

So why should work be any different?

Oh, I think work should absolutely be the same.

And I think what we're talking about here, and the reason that I have work as a coach and you have worked as a podcast host and everything else is that the people part of this, the relationship part of this, is hard.

It takes effort.

It takes making mistakes and figuring out what works and what doesn't.

And it takes energy that we don't talk about very often as we're thinking about KPI's and deliverables and quarterly goals and moving the ball forward on the business.

This stuff that we're talking about here, to me, this is the stuff of leadership.

It's the reason why I'm involved in the work, and it's overlooked at your own peril.

I agree, because I think if you had these conversations, then your work relationship could be stronger, which then can affect your meeting those KPI's and all the things are intertwined because, you know, they're not isolated.

And I think if we could figure that out someday for the whole world to do with, maybe we shouldn't, because then you might not have a job.

So we'll make sure that we still have some strife for you to help with.

But, you know, I think I love that you found this space for yourself, and I know that it's helping other people, and I'm sorry that you had to experience that, but I'm kind of glad you did, because now you're able to help people this in this full time way that you do.

So I always look at these, I try to find these silver linings now at this point in my life of some of these moments.

No, I appreciate that.

And I've had plenty of small t work traumas, I would say, and I could go back and list them one by one.

And every single one to a moment has some sort of a positive outcome later on down the line, either because it led directly into something that turned out to be great, as in when I hired my first coach ten years ago, and now I am a coach and I'm working for her, and life is good to you know what?

This was not a positive experience for me, and I learned a tremendous amount about the sort of leader I choose not to be by watching the example of somebody else.

Exactly.

There's always something to learn from it.

I even say it, had my mom not died, I would not be this person.

And all the struggles that I went through, I would not be this person.

And so in some weird, disturbing way, there are some silver linings from the experience that I had as a child and all the mistakes that I made along the way.

And so I think there's always a place to learn from whatever we experience, if we choose to learn from it.

Yeah.

And I think it's evolution to be in a place where you've experienced something that is the loss to end all losses as a young person who maybe even doesn't know what loss is intuitively at that point, and something that you would never seek to repeat or wish on another person, and at the same time, you kind of don't want to give it back because it's brought you to who you are.

Exactly.

Yeah.

It's a challenge.

Speaking of going back, I like to wrap up these conversations with a question, and I'm wondering if, like, this entrepreneurial five years in, Alan could go back to Alan that was about to walk into that meeting.

Would there be anything you would want to tell him?

Wow.

Well, I would lose the element of surprise if I had inside information.

And I think the.

The surprise and the shock of it all was interlaced with the actual content of the conversation, of which there was not much.

You just walk on by.

Yeah.

So there might be a small amount of, like, hey, don't take the meeting, or, hey, maybe there's some value in you deciding when the meeting is over and getting up and walking away, rather than, like, sitting and tolerating the whole thing.

Maybe there's something better by way of comfort that you could offer the colleague who's clearly suffering through this experience with you.

But otherwise, I don't know that I would go back and make too many changes.

Yeah.

Just like, high five on the way in.

Good luck.

You got this.

And it's going to lead to things you can't imagine.

Yeah, it's.

So how fortunate are we when we have the ability to look back on those moments and reflect on them in a way that isn't, I guess, in a positive ish way.

You know, I think that we're the lucky ones because I don't think a lot of people are there yet in some of these moments because we are taught, like, we started this conversation.

I think there are elements in society that tell us that being a victim can be helpful or, like, we can live in it and certain things can come from it.

And I did that for 20 plus years, and it served me in the way that I needed it to.

I guess but now I'm at this place where I'm able to reflect on these moments and go, wow.

You know, like, that taught me a lot and I'm thankful for it, for sure.

I think that is wisdom and that is age.

Thanks.

No.

If people are interested in learning more about you, connecting with you, finding out about your coaching services, what's like, the best way to find you and get in your space?

Sure.

So peacefuldirection.com is my website.

Peaceful direction is the name of my coaching practice, and it has information on the services that I offer, how to get in touch, how to schedule an exploratory call.

I'm also on LinkedIn a lot.

It's the only social network that I use, so it's pretty easy to find me there as well.

Good on you.

Why LinkedIn?

Because it's where your audience is, essentially.

It is.

And it's the place where you talk about work, and it's the place where I don't get drawn into distraction with memes about people's cats and that sort of thing.

I leave that to my wife and daughter to tell me what's interesting and funny, and I look at it when they're interested.

Hey, that's probably the smarter way to do it.

You also probably have an alarm clock instead of your phone.

I do.

None of our phones live in the bedroom.

It's a family rule.

I love it.

Well, thank you for sharing your story in this way, letting me ask the questions in the way that I did.

I really appreciate you being a part of this journey.

Matt.

This has been a delight.

I am so glad for the opportunity, and I feel like I learned a lot about myself through the questions you were asking.

Well, that is a compliment and I will take that.

Thank you for that.

If you are listening and something that Alan said stuck out with you and you want to reach out to him, please do that.

But also, if there's someone in your life that you think maybe needs to hear Alan's story because maybe they're going through something similar and they just need that little, oh, I'm not the only person going through this.

Why don't you share this episode with them?

And with that, I will say thank you.

And I will be back next week with a brand new episode of the Life Shift podcast.

Thanks again, alan.

Thank you.

For more information, please visit www.thelifeshiftpodcast.com.