Alan Heymann on Making Successful Career Transitions

Transcribed from the episode audio by AI, so it may contain mistakes.

Ravi0:16Well, I'm joined today by Alan Heymann, executive coach. I'm looking forward to this conversation. Alan, thanks for joining.

Alan0:25It's a pleasure to be here. Thanks so much for the invitation.

Ravi0:29Well, we met online, as happens to many people nowadays. And I suppose you found me online and reached out. I think you found my podcast. And I clicked on your website, which is Peaceful Direction. and instantly thought, okay, I need to have a chat with Alan and see what's up. Do you remember how you found me? So

Alan0:54my recollection is a little hazy because it's been a few months and we're in, we all have pandemic brain to some extent these days. But I think you interviewed somebody I was either interested in or new on a prior episode. And I thought, you know, if there was some overlap of things that I was interested in, maybe I could bring something interesting to your audience as well.

Ravi1:13Yeah, it is amazing how that just follows. knowing curiosity or interest leads somewhere really cool. But I'm glad we have a chance to explore, you know, your background from being a lawyer to being an executive involved in the water industry. And I interviewed a friend Adam Tank who worked in the water industry, which may be the connection. Yes, I know, Adam. That's

Alan1:37what it is done. Absolutely right.

Ravi1:40He's on an earlier episode. And everything from your interest in meditation to running. I think there's a lot of threads here for us to explore. But let me just hand it over to you. I mean, tell me and everyone listening a bit about yourself and your background and also what you do now from a coaching standpoint.

Alan1:59Sure. Maybe I'll answer the question backwards. So I have a coaching practice. It's called Peaceful Direction, as you mentioned. And my specialty these days seems to be along two tracks. And there is some overlap between the two of them. So I coach a lot of introverts because I am one. and I know very well the dynamics of being an introvert in an extroverted world and how it can be a superpower rather than a hindrance. And I coach a lot of leaders in transition. So folks who are looking for their next thing and need some help getting there along the way, or folks who have recently undergone a big transition, a promotion, a new job, a new career, and they need some of that scaffolding to help make them more successful.

So that's primarily where I'm finding my clients these days. What else can I tell you? I'm in my mid-40s. I live in Montgomery County, Maryland, with my family, have a 12-year-old daughter and a dog, have a bit of a running habit, as you mentioned, and have followed a plant-based diet since 2002.

Ravi2:52So maybe we can go back a bit to your own transition. You help leaders in transition. It seems like you've had a transition yourself. And I'm always fascinated with what inspires people to make a shift in their life, whether it's changing a role at a company, changing companies, changing careers, moving where they live. I mean, I've experienced all of the above a few times in the past decade. And what inspired you to move in a coaching direction?

Alan3:27Sure. So I think this was the latest and perhaps the biggest in a series of transitions. Went back at some point not long ago and figured out, I think I've had 14 or 15 jobs during my career. So this has been fairly frequent. And this one was different because I found myself at the end of the transition working for myself for the first time in 20 plus years as an adult. I've always been somebody else's employee, never been self-employed until, you know, this recent transition. And I think what it comes down to is I discovered the power of coaching as an employee and as a client of a coach seven or eight years ago at this point.

And I held that with me. And I had the opportunity to go to coach training, got my coaching certificate at Georgetown, as many of my fantastic colleagues have, and was thinking for a while that I would have a job that involved some elements of coaching. And it just didn't for a variety of reasons. So on the one hand, there was this collection of responsibilities that I had that was becoming less and less fulfilling to me. And this thing that I was really interested in and wanted to dive into wholeheartedly, but I didn't have the I made a plan.

I saved up some money. I found some clients on the side, was coaching a little bit at night and on weekends, primarily people in different time zones so I could do it after work. And then in November 2019 is when I jumped out and launched my full-time coaching practice, which in hindsight turns out to have been just a few months before the pandemic started.

Ravi4:58How did you know if you can think back to that moment of insight, if it was an insight, were you transitioned? How did you know you were ready to leave? Well, maybe before we get there, you were working in industry as a leader for a while, right? So you had like over a decade of experience, right, 15 years or something like that. So what was that, what was it that made you say, okay, now I'm jumping? Was it a moment like that where you said, okay, now I'm becoming a coach, or did it, was it more of a gradual?

Alan5:35You know, there wasn't a solid. inflation point, I would say. It was more like a growing awareness that this was something that I wanted to do more. And I found myself frustrated with some of the dynamics that we all have to face when we're in organizations. There are office politics. There are leadership challenges. And I couldn't devote the time and attention necessary to sharpen the skills and get good at the craft that I had recently picked up by going to coaching school. So, you know, I don't think it was ever a moment in time where I just knew this was a thing that had to happen.

It was just something that built up over a period. And I'm a fairly risk-averse person. And I have not taken big leaps of faith much in my career in the past. This was a bigger one. I felt comfortable with it because I knew we had some cushion around us. I knew that I had had some early successes in coaching with clients that at least gave me a sense that this could be viable. But what I didn't have was, you know, the grand spreadsheets and the five-year plan and the growth journey and all those things that people often feel like they have to have when they're jumping into a business.

We're fortunate in this line of work that our overhead tends to be fairly low. You know, you don't have to take out loans to build out of space or buy restaurant equipment and things like that, hire staff. So most of what we make, we tend to keep. And that combination of low overhead and slow building has proven to be very successful for me over the past few years.

Ravi7:05Do you get a chance to apply much of your law degree to what you do now, or have you ever put that into practice? Well, it looks

Alan7:14really nice sitting on the wall right behind me here. So that's the first thing. You know, I never practiced law. So I went to law school at night when I was working in municipal government, and I made some fabulous contacts. I wanted a lot of things about the constitution in the courts, which is what I was aiming for. And it has been helpful in that it helps me put some things in context. So I coach lawyers and I have some common understanding of the language that they use and the issues that they face.

And I can read contracts. And I'm not afraid of, you know, signing something before I have some expert look at it because even though I've never been a contracts lawyer, I have some familiarity and some awareness. Beyond that, you know, I think the major asset of law school in terms of how it helps you think is that that you are required to consider things from different points of view. You're required to be able to argue a case from two different sides. And as coaches, we reframe things with our clients all the time.

We ask them, have you considered looking at it from this angle or from this person's point of view? So that has been helpful as well. But as far as a direct link between lawyering and coaching, it's a little more abstract than that.

Ravi8:20As you talk about that, I can see a lot of parallels being able to have a shift in perspective or to see both sides or to see a bigger picture from a smaller picture. I see how that can apply. And some of my friends who have gone through legal training but are not practicing lawyers, I find that they also have just a way of communicating clearly. Though obviously legal documents can be arcane, I find in conversation, there's a level of clarity with my friends who have been to law school that they seem to have.

if it came from their legal training in some case. For

Alan8:57me, it's hard to pull apart the lawyer and communications person parts of my background because they're kind of fused together. The other thing that I'll say is one of the earliest things that I learned in law school was that I did not want to be a litigator because I don't have the temperament for it. I just don't. Litigators are awesome. They're problem solvers. They help us move society along in many ways. And I also know that that's just not me. I don't have the instinct to win.

at all costs. I don't have the instinct to destroy the other side when there's an argument or a discussion. So my favorite classes in law school were actually the alternative dispute resolution set, the mediation, negotiations, the types of engagements where everybody gets a little bit of something out of the deal. And I find it very familiar because I know a lot of coaches who also do mediation.

Ravi9:46Yeah. So I want to, before we talk about your specific practice, you You mentioned you've worked with coaches before, and would love if you can share any experiences that were memorable and impactful for you based on what you got from a coaching relationship that maybe planted some early seeds that you wanted to do this yourself. Absolutely.

Alan10:13My coaching origin story is one of my favorite stories to tell, in fact, because it came at a moment where I really did need a coach, but I did not know what coach was. So I was working, heading up the communications function at a large international nonprofit. And I was in that job probably about nine months before I realized I was drowning and I needed some support. And I didn't know what that could look like or where it could come from. And meanwhile, all these expectations placed upon me because this was the biggest job I'd ever had.

And I was working in an organization that I was personally aligned with. I had friends who worked there. I thought I was going to retire from this job. someday that this was it and I had arrived. So I went to see a colleague of mine on the executive team who was not my boss, but she actually was going through the Georgetown coaching program at the time in addition to having an executive level function at a big nonprofit and commuting from D.C. to Florida every week because that's where her home was.

And I took notice of it because it seemed like the kind of thing that was important enough to her to be able to devote that kind of time and attention to it. So we talked. And the end result of that conversation was that I hired one of her classmates and became this coach's second ever paying client as she was transitioning from a big corporate job into a full-time coaching practice. And she was in North Carolina. I was in D.C. at the time. So we talked only by phone.

We never met up in person for coaching. And I would come home at 7 or 8 o'clock at night and flop down on the couch and call her. And what we were able to do together was was simple but essential. And she helped me understand what my stuff was. And we all have stuff. You know, I had really. roadblocks and limitations and obstacles and blind spots versus the institutional stuff that likely was never going to change. And making that distinction for me helped me understand the situation I was in in a way that was extremely helpful, that was extremely tangible.

And I ended up leaving the job, not long thereafter, and going into a much more fulfilling situation. But what coaching was able to achieve for me never left. And the more I started to think about it, the more I realized it's a discipline that kind of knits together various things that I've enjoyed doing throughout my career and gotten fairly good at, if I can say that. So I started as a reporter. And what do reporters do if they're good at their job? They ask powerful questions.

They elicit information and stories and answers from the people that they're interviewing. So of course, there's no audience in coaching. It's one-on-one. It's confidential. But it is a similar set of listening skills, if you do it properly. Loved bringing along emerging leaders during the course of my career and loved communicating. which is, you know, at its heart what what coaching is. And so many of my clients come to me with questions about executive presence and how they're showing up in their workplaces or introvert issues. And all of that has to do with communication.

So it's it's solidly in the middle of what I've been doing for a very long time.

Ravi13:12Give us a sense of your client base right now. Who do you work with? Who do you help? Sure.

Alan13:20So I have clients and work in several different buckets. And the first bucket, which I think is a great thing for me and for many other coaches, is that I do a fair amount of contract work. So there are large coaching providers that have sprung up in the last 10 years or so. And they will bring in big institutional clients that need 100, 200, 1,000 people coached at once and match up the coaches to do the work. And I was lucky enough to get engaged with one of those companies early on in my coaching journey as a practitioner.

And that enabled me to coach people on the West Coast and in Europe and in Asia and in sectors of the economy where I've had no connection whatsoever. I know you worked in technology for a long time. I'm a nonprofit and government guy from the East Coast. So no reach into health care or finance or any of those types of companies. And I got it. So I got the experience. I found the clients. Very engaging experience that I've had with that. So I do probably about a third to half of my work there.

On the private side, I do almost exclusively individuals and occasionally a little bit of organizational work. And these are folks who are probably mid-career. I do work with a few emerging leaders. I've had, you know, one experienced CEO who was looking to make a jump into another position that would probably be his last. And I also coached somebody who was just coming out of undergrad and trying to figure out this whole working world. So I've kind of run the gamut of people's ages and levels of experience.

But I tend to get the introverts and I tend to get the folks who are curious and they're ready for some sort of change in their lives at this moment. And that readiness brings them to me. And at this point, given that, you know, I'm a couple, three years into the practice, I don't have a huge following in terms of strangers who, you know, encounter me on my website and come, you know, hear me speak and then become clients. Most of the people that I'm coaching on my private side are one, two, and three degrees removed from my existing network.

It's a lot of word of mouth. It's a lot of referral, which is not, you know, the greatest way to drive volume if you're really looking to scale up your practice by leaps and bounds. But I'm keeping up with the workload and enjoying the clients very much. So it feels very authentic to me at this moment.

Ravi15:36Yeah, exactly. Exactly. I can definitely relate to that experience now on, I think eight years in, but still feel like brick by brick, client by client. it builds. But I'm interested in, let's talk about transitions because you shared your transition. And maybe we could talk a bit about what you're seeing with clients and transitions right now. Where are they challenged in transitions? I can imagine, well, I've seen in my own practice, predominantly working with leaders in tech. If you're in a role for more than two years, you're like the veteran.

And I stayed at one company for my entire corporate career. I was at Microsoft for about 14 years. But I see many clients, you know, every couple of years, they're moving around. And if we, you know, don't consider that good or bad, it just sort of is what it is. People tend to move or companies change quite quickly in certain industries. I'm guessing you're seeing some of the same types of things with your clients. So maybe speak a bit to what are you seeing regarding clients looking to transition now?

Is it accelerating, decelerating? Where are they stuck in their transition process? I would love to hear your take on.

Alan16:59Absolutely. So for one thing, I think we're in a great moment of transition. In that, certainly I've had a number of clients approach me to prepare for transitions, as I mentioned, but I've been fairly often surprised by existing clients bringing these surprises about upcoming transitions of their own. I'll be coaching somebody for four months and then they'll say, you know what, I've decided to retire in the spring. And I'll say, well, that's interesting. We didn't cover that two weeks ago during our last session. I think what has happened is that the pandemic has forced a look at priorities.

And a lot of us are thinking about what is important to us within, but also outside of work. And the things that we really need to have out of this employment experience versus the things that we would rather live without. So a lot of that work has already been happening among the folks that I'm coaching even before we get into the session, but we can certainly talk through it and unpack it together and we have. And then it's just a question of, you know, folks are oftentimes a little hesitant to grant themselves permission to dream a bit, permission to imagine, permission to think about what could be.

They may have become ingrained with this idea that they have to accept a certain set of conditions as fact or as permanent when a lot of evidence to the contrary seems to be coming up these days, you know, across the economy. So one example would be folks who are thinking about transitioning into a different line of work or perhaps a different employer because they're having certain requirements placed on them in terms of return to office. And that is perhaps fueling some migrations these days. if you've gotten used to working from home because you're an introvert or because you have a two-hour commute typically when you're going into your office or you have small children or parents who need care for, you know, that sort of thing.

You can make choices like that these days because companies are differentiating themselves in terms of what they're requiring. So helping folks understand what their negotiables are and their non-negotiables are is a key part of planning for a transition, And I think what is also happening with a lot of folks going into freelance work, perhaps more than ever before is we're seeing more and more models for how this could work, And those models are going well beyond the traditional nine to five butts in seats going to the office every day kind of model, even looking at some part-time or job sharing type of arrangements, or people who are retiring early or taking gap years, or a good friend of mine that I know from the coaching universe has a practice advising would be digital nomads on how they can put their lives together in a way that is completely location independent, which is something that I know plenty of people did prior to the pandemic, but it's become a lot more obvious that that's an interesting thing to do these days.

So the menu of options is vast. I think part of it starts with just making sure people are aware of what they can have access to. And then, you know, we all make these these calculations in our head about risk and reward and what we need and sometimes it can be really helpful to sound through all of that with a you know a disinterested third party

Ravi20:06How do you help a client? Let's let's suppose a client comes to you. They've had a career. Uh, let's say they work for 20 years. They have an ang, this, this growing feeling of dis-ease or angst, or sense that they're not. They're not firmly situated where they want to be in their work. They don't don't know what's next, Like where do you even start?

Alan20:31I think it starts with values. I think it starts with what is important to you, you know, in your being in terms of what you believe in and what you want the purpose of your work to be. And some people have that, you know, they can, they can rattle it off, you know, at the tip of that. And some people need some exploration on that front. They really need to sit down and give it some thought because maybe they never have or because that list just hasn't been refreshed in a couple of decades.

So that's the first thing. And a lot of times that that feeling of angstiness, you know, or unease, as you called it, comes from a growing sense of misalignment between your values or purpose and what you're actually doing for a living. Or it's just gotten stale after a while. And you didn't realize it until you had a slightly new focus on what you've been doing. So, you know, I've worked in plenty of sectors outside of tech where longevity isn't a limiting factor. It's a an asset.

And what happens then is you've just sort of been out of the field for so long that you're not really sure how to go about starting. And that's a great place to engage with a coach. You know, what do you do in terms of encapsulating your experience over the last 15 or 20 years into a phrase or a sentence or a paragraph? What do you do in terms of stating the value that you might be able to provide to a prospective employer that could be in a different sector or a different part of the country.

These are things that you can sound out very well with a coach, and that can be very helpful.

Ravi22:02In your experience, I'm assuming you were like me, perhaps at some point, you know, buying nonfiction books, self-help books on, you know, design your career, explore your values, find your value. You know, I used to go to Tony Robbins seminars in my early 20s and all kinds of stuff. And while I got value out of some of these things, reading books or sitting with worksheets and workbooks and doing all this stuff, I've never have the kind of insight that's come from either my quiet reflection independently or co-creating and reflecting with a coach.

And I'm just curious for you, what is different in your view of how you see clients revealing their values in dialogue with a coach versus just sitting down with some worksheets are reading a book and thinking about it on their own. Yeah.

Alan22:57And I like to think that there is plenty of room for both. So I am one of those coaches who is constantly flinging forth resources, you know, either to people who read my email newsletter or to my clients in that if an issue comes up in a session, obviously I'm not the expert on it, but I'm pretty good at figuring out who the experts are. So if you give me time management or delegation or executive presence or something along those lines, I'll share with you what I think is the best book on the topic and you might be able to go read it and have some insights that we can talk about in a future session.

But in terms of self-service versus having some support, I think there's a couple of ingredients that are different. One is a thought partnership. And the thought partnership is a person who will challenge your assumptions, who will question your beliefs, who will reframe things, who will reflect back what you think that they're saying in a way that they may not have thought about before. And having that slightly different, slightly shifted context or perspective is incredibly valuable. And you can't get that from yourself looking in a mirror.

You can't get it from a book that doesn't know you. And you can't get it from your boss or mentor or spouse or sibling because they're all vested in the outcome and a coach isn't. And the second thing that I think is incredibly valuable is accountability. So, you know, it's one thing to read a book about changing your relationship with email, let's say. But it's another to have a conversation with your coach about how stressed out you are about work. And you can't believe, you know, your vacation is coming up tomorrow and you have so much to do.

And your coach is going to ask you, okay, how many days can you go through your vacation without checking your email? And you're going to say, maybe one. And your coach is going to say, how about two? And you say, okay, two, I guess maybe I can do that. And then sure enough, two weeks later in the next session, your coach is going to ask you, how did it go with those two days of being on vacation without checking your email? And you're more likely to do it if you know that person is going to be sitting there asking you that question two weeks later than if you decided to do it yourself.

Accountability is incredibly important. And I've relied on it time and time again in coaching relationships of my own.

Ravi25:06I've just found there can be, you know, being on the with people. There's something quite fun also with having this be a be a partnership versus just all right, now I got to figure out what I want to do versus having my team or my coach with me exploring with me. It could be really fun to be together on something versus just having to go it alone. And I personally find that quite fun. And yeah, there is a nice accountability. That can be I've always taken the accountability as being, oh, isn't that nice?

Someone cares about me to ask versus, oh, God, I got to perform for my coach now. Better get the task done, which obviously is the other side of accountability. So just going back to transition. So, okay, you've got values, you know, clear on what you want, what you really want. Like, what's next when you think about helping a client who is really taking a hard look. And I completely agree. in the pandemic. I've seen, you know, just to put a rough percentage on it normally about, and I generally am working with clients, some who already come into coaching, thinking they need a new role.

But I'd say two-thirds are content in their work. They're just trying to be better leaders. And generally in my practice, about a third of clients at any point are realizing, hey, I need a transition. I'd say now it's more like two-thirds are questioning what is that they want to do. been pretty dramatic over the past year, how that dial is swung in the other direction. So I completely sort of agree there's something in the air, if you will, people waking up to the fact that there are many ways of working and questioning what they really want out of life, not just out of work.

But what do you do once you, okay, once people are starting to get clear on what they value, I mean, what's, what else goes into this whole transition process?

Alan27:11Yeah. So the next thing that I I would probably ask someone to consider is this. And I'm very fond of using analogies in coaching, both analogies that come from my own brain, but also sometimes the clients will throw them in themselves. I'm actually collecting these to do a book project on it at some point. So one of the ones that I've been using a lot lately is to imagine that you are packing to move to a different country. So you're moving house from one nation to another.

And so you know that there's going to be a lot of shifting a lot of moving around of different parts. And so the first thing you're going to need to do is pack your backpack for the plane run, which is going to be long. So what is it from your existing set of belongings in your apartment in the first country? Do you absolutely need to take with you to have right away for the journey to the second? Those are the essentials. So I ask them to consider what are the essentials from your current employment situation that you feel like you can't go without?

You have to have them regardless of where you are and where you're going. That's the first thing. And that could be anything from, you know, access to my boss on a regular basis to get support and direction, to, you know, a certain focus for my responsibilities, to a certain size of a team, to a certain salary. These are the must have. And the second thing I ask them to think about is what is the first collection of things that are going to go into the dumpster as soon as you've made that decision to move?

What are you giving up? You know par for the, you know absolutely must get rid of right of way. And this could also be anything. This could be for example, I've decided that I don't want to supervise people for a living anymore. I want to go back to being a highly skilled individual contributor. Okay, So we're throwing leadership into the dumpster for the moment, et cetera. And I think once they have a pretty clear list of what has to stay for the moment and what must go, they can start working in the middle a little bit.

The things we're going to pack up and send with the movers that aren't going to show up for a few weeks, or the things that might be nice to have, or the things that we might be hoping to pick up along the way, like the new furniture and curtains and things like that. So envisioning a move like that, then, can be helpful. Also, I will ask them if they've seen examples of the type of work or the type of role elsewhere is one of the things that I always go to with you know, especially people who are looking to make big leaps, or leaps that are just very different and challenging is this notion of almost find who you want to be when you grow up.

Ask that person You want to have a podcast, What's your favorite podcast? Let's see how they got started. Let's see if you can reach out to them to get 15 or 20 minutes to see what the journey was like. And maybe there are some lessons there for you, some steps that you can emulate.

Ravi29:55Right. You know, when you, when you were sharing the pack your bags metaphor, I remember when, you know, as a family, we used to go to, I was born in America, but my family's from India originally. And whenever we would go back, we would take, you know, suitcases in suitcases. So we'd have like extra suitcases that we'd take goods from America that you couldn't get in India, I mean, back in the 80s, right? And then you have extra suitcases there. And so you show up and you have just space for new.

And we would never know what we're going to bring home. But there was always something. And so as you were, as you were speaking, I was thinking, well, what's nice about the move is I get let go of a bunch of stuff. stuff and I have space, and then in that space, new stuff will come. Yes.

Alan30:41And the openness for potential in what that new space could be filled with. Exactly,

Ravi30:45exactly. I mean, I used to always wonder what, like, why are we taking almost like these Russian nesting dolls? We'd have like suitcases in suitcases and suitcases. And my dad would always say, hey, you never know what we're going to find. Yeah. And he was always right. We always found stuff to put in new suitcase.

Alan31:04I love the image of having luggage for your luggage. Yes,

Ravi31:07exactly. So that was really good. And then, you know, for me, just to sort of share a bit on transitions, I completely agree with what you're saying. And I don't know, it feels like many people forget what it's like to really explore. You know, I remember what it was like when I was in college. And well, did you, did you go into undergrad with an idea that, okay, you were going to go to law school?

Alan31:37I didn't. You didn't? But I went into undergrad absolutely with the idea that I was going to have a long and successful career as a broadcast journalist. And that was the last time in my life that I had a big plan like that. And that career lasted exactly three and a half years. Okay.

Ravi31:54I went into college. At first, before I applied, I thought, well, I was going to be an engineer because my options were, well, all the models of, you know, okay, going to be a doctor or an engineer that my parents were. And then very quickly realized, I don't quite have the knack for this engineering. I loved computers. I taught myself how to program, but I didn't want to go into the depth in that field. Then I thought, oh, I want to go into finance. So I majored in finance.

And I was like convinced that was going to be it. And then as I started to get internships, I realized, I don't know what I want. And I started to just explore and sort of be less beholden to my plan. And I know my friends also, we were all like, I don't know what I want. want to do. But we just picked a direction and then we're open to change. And then I also remember as I got into my corporate job, I almost felt like, and this was totally made up in my mind, my direction had calcified.

So like, here I am. This is what I'm doing. And once five years passed and 10 years passed, it sort of got fixed. Of course, that was just a thought, but it felt that way. And so it It seems to me that there's something about realizing that exploring can be just as much part of our nature as having a goal and being, you know, trying to climb the proverbial mountain. But we tend to forget that, that idea of everything's up for grabs. You know, we can try different things.

I mean, it sounds so simple, but kids get it. And I think we all get it at some point in our schooling that we don't really know what we want and that's okay. But as adults, we forget that we can be just as playful and exploring and sampling at the buffet of careers later in life as we did earlier for many of us. It's a good

Alan33:40reminder. And I totally agree with you that kids are absolutely better at this than than adults tend to be. I think it gets socialized out of us at some point. And I also think that the older we get, the more responsibilities we have, the more complex our lives become. we just sort of struggle under the weight of everybody's expectations for us. That's how I look at it. And other people's expectations can be very empowering. So if we don't believe we're capable of something or we don't see ourselves headed in a certain direction and somebody that we know and trust says, have you thought about this or what if you did that?

It can take us in a place that's absolutely wonderful. And I've had the benefit of a few bosses and mentors throughout my career who did exactly that for me. So they freed me up to be thinking in different ways. but other people's expectations can also do exactly the opposite and they often do. So if people are typecasting us into a certain role in their lives, in their companies, in their organizations, it's very tempting to just stay stuck in that mold for a very long time, longer than is helpful.

Ravi34:45You know, the other part, I suppose if we were to think of this transition as you're saying, okay, get in touch with what you want and then, you know, start moving toward it. Now we can maybe talk about the, okay, now you've picked a direction. And then there's what happens then. And I would love to hear just in your own personal transition. And it could be your transition into coaching, which might be more recent and fresh for you or another transition. But what were you and maybe right now having to work through?

What were some of the challenges and struggles after you picked the new direction? You started making your moves. and then reality met, you met reality. And I'm assuming there was some friction there, some challenges, maybe if you'd be open to speaking with some of those that you faced personally and then how you got through those. Sure.

Alan35:39Well, no job experience turns out exactly as you expect it to turn out. There are always challenges, there are always growth opportunities. And, you know, looking back on my own career, I think, you know, it is tempting to think that my experience is typical when perhaps it may not be. But when I'm speaking with folks, you know, maybe not even coaching. Maybe if I'm just talking to friends of mine who are looking for new positions or people I know in my network, I think there tends to be this focus on volume and looking for posted opportunities.

And my experience is that that's not typically how things have worked for me. So I've been fortunate to have people looking out for me during the course of my career all the way through. And looking back on 20 plus years of professional experience before joining my coaching practice as a sole proprietor, I had exactly one job where I applied cold to a listing that was posted someplace and got it. It was probably the worst job I've ever had, and it lasted about nine months. So everything else, someone has said, hey, you should take a look at this or you should talk to this person.

And I think sometimes people can have a reluctance to activate their networks in that way because they're concerned about what it might look like to hold themselves out as wanting to try something different. And that was something that I thought about when I launched my coaching practice. What's it going to be like for me to go to all these people I know on LinkedIn and all the people I've worked with in past jobs who know me as journalist, communicator, leader of a communications team, perhaps marketing person, maybe lawyer, and say, hey, here's this thing it's different that you might not have heard about.

It's kind of interesting. It's kind of new. It's related to what I've done before, but it's different. Here's why it's important to me. Will you please look out for opportunities? Because I need some clients. That's a moment of vulnerability. That's the sort of thing that I didn't approach very easily. One, because of concern of just kind of being ignored or people having questions about why now or what makes you think you're good at this after all this time and doing something else. And secondly, because it just doesn't come naturally, it had not prior to this experience come naturally to promote myself.

So I was a communications guy for 20 plus years before becoming a coach. All the techniques, all the tools, all the conversations about promoting somebody else's program, candidacy, agency, product. And suddenly, I was the product. So I had to get over that before I was willing to put myself out there as somebody who was worthy of everybody else's attention. Why should they care? And I realized, well, wait a minute. So, yes, you're an introvert. Yes, you've been building a career talking about other people's stuff for a living.

But you have an ego. You started your career on television for crying out loud. Get over it and just put yourself out there. And that is what I started doing. And I've had a lot of conversations with folks that have not led to clients that have not led to new business, but just have been nice, friendly reconnections for no other purpose than that. And that has been lovely in the last couple of years.

Ravi38:56How did you get over here at Nico? You said, you just got over it. How do you, how does one do that?

Alan39:05Yeah, I don't know that you ever get over it completely. That might be an oversimplification on my part. But it was more along the lines of, you know, this comes up in sessions with clients a lot as well, because those of us who are perhaps a bit more reserved, those of us perhaps who harbor a bit of social anxiety, we're not the first ones to put ourselves forward. And I do work with clients on that a lot. And what I do is to help them understand this is not self-serving work that is necessary here.

This is work that is necessary to elevate the profile of the team, of the business function, of the organization where the person is working. And they need that person as the leader to do that elevation because it lifts everybody else up and makes them more effective and gives them better access to resources. So understanding that they're doing it for a group of people beyond themselves and understanding that they're doing it for a purpose that is larger than self-interest is where I go in the coaching. And it's also where I went for myself.

So I'm coaching because I believe in the practice, because I think it is useful as it was useful to me. But I'm coaching for the people that I coach. I'm coaching for my clients and coaches and their organizations, and the impact that I have will ultimately touch the thousands, if not tens of thousands of people they'll be responsible for over the course of their careers. That is a huge potential impact that goes well beyond myself. And it makes me so much more comfortable to think about it in those terms rather than, you know, I'm going to try to be the next whoever that has the, you know, a million-dollar book deal and has all these followers and is making money off of.

all these different endeavors rather than the one-on-one work and a small group work that I prefer to do at this point.

Ravi40:49It's like, you know, I find that we'll often do more for others than we will for ourselves because we get out of ourselves when we're helping others. Like we recently moved, and before we moved, a neighbor had an issue. They needed some help with their house. And I spent an inordinate amount of time helping and I didn't give a second thought. It just was such a natural thing. And then I came back home and my wife asked me, hey, what were you doing? I'm like, oh, I'm just helping them out.

They're trying to fix this thing. And she's just like, you know, ours is broken too. It was like a sink disposal thing where I was helping a neighbor, but my own was still not fixed. And I just laughed in response. But there is something to that. I think you're onto something when we get out of our own ego or what's in it for us. We connect to something much bigger. And it's a whole lot easier. to do do things when we see the bigger picture and the connection to others.

And, you know, I, I, the what, how'd you got it, get over your ego question. Part was inspired by the picture you have on your wall, those listening. There's also a YouTube video of this interview with Alan that I'm doing. And you can see in the background, there's a, there's a photo of the Dalai Lama and Alan and would love to hear just to segue a bit. what's the story behind that photo?

Alan42:15The photo of him shaking hands with a much younger and less gray-haired me, yes. And much taller of them. Yeah, right, because I'm sitting down. So I was working for a D.C. council member back in the mid-2000s. And I was a constituent services rep. So my responsibility, in addition to communications of the website and that sort of thing was potholes and streetlights and all manner of things that you need your municipal government for. and we became aware probably a couple of weeks before the fact that the Dalai Lama during part of a recently planned visit to D.C.

was going to be visiting a charter school in the ward that my council member represented. And he was sort of going back and forth on items related to the upcoming schedule in a meeting that I happen to be attending. And he said, you know, I'm not sure I'm going to go to that. And so pause, with that idea for a second. I'm not sure I'm going to go to that. And that's stuck in my head. And, you know, I was a much younger person back then, probably a lot less assertive in terms of my own opinion and what I wanted and needed out of life, especially in a professional context, especially working for an elected official.

But somehow, in that moment, I had the presence of mind and this meeting full of people to say, of course you're going to go. And I'm going with you. And so I found myself a couple weeks later in this public charter school in Ward 1 in the District of Columbia in a receiving line of people to shake hands with the Dalai Lama. And we had a very, very brief conversation. I remember it to this day because, of course, who wouldn't. And, you know, what's very interesting to me is in all of our recent discussion in the United States in the last couple of years about race, which has been very enlightening and educating for, me, among others, there's this concept that people of color and immigrants in the United States are constantly being asked, well, where are you from?

I was born in California. No, no, no, where are you really from? So I'm bringing that up to tell you that that was actually the conversation that I had with the Dalai Lama. And so he says, hello, how are you? What's your name? And he basically asked me, where am I from? And so I said, Chicago? And he said, no, where is your world community? Mexico, perhaps? And I said, no, I, you know, my mom. mom was born in Israel. My dad was born in the United States.

Okay, well, nice to meet you, etc. And that was the end of the conversation. But I got, no, where are you really from by the Dalai Lama, which is, you know, the highlight of my moment there. So I had given my boss a Washington National's baseball hat to give the Dalai Lama as a gift and the Dalai Lama duly put it on his head for the photo op. And I realized in my meeting with him and in just, you know, experiencing his presence, somehow I had the state of mind to recognize that there was an associated press photographer sitting in the front row very near where I was standing at the time.

And I knew this person because he lived in our ward. And I had helped him with a streetlight issue that same year. So when I got back to my office and I emailed him, I said, by any chance, if you happen to get any photos of a tall person with a beard and a gray suit, could you share? And he said, yes. And now I have the photograph for all of all of posterity. So that's my Dolly Lama story.

Ravi45:34Are any meditative practices part of what you do? And how does that, if so, how does that weave into your coaching as well?

Alan45:43Well, so I have a daily meditation practice, which is often calming and often frustrating, I think, as many of us who do this kind of work, no. There's this image among people who don't meditate regularly, I think, that we're all just sort of like blist out and sitting silently absent of thought for long periods of time on end. which is not at all my experience. But I do try to sit quietly, you know, in contemplation for a few minutes every morning, usually over my first cup of coffee, usually before anybody else in the house has gotten up.

And I find that it just really sets the tone for the day. It gets me centered and aligned. And at the very least, if the thoughts are flying back and forth as they often do, I have the ability to process them and set them aside once I'm done with the meditation itself. I often, I will find myself heading straight for a notepad after. after that daily sitting experience. But yeah, I've been doing it for a number of years with some regularity. And I think it really lends a great positive element to the way that I prefer to start the day.

Ravi46:45And for you personally as a coach would love to, well, I'm really interested in meditation and mindfulness practices and all of those things. I know there are some people who, you know, they're just naturally quite content and maybe don't need meditation if I could even say that. Some people probably don't need it as much as I do, but I've benefited a lot from various yoga and meditative practices. You know, when you're working with clients, does any of this seep its way into your work with clients?

It could be meditation or anything else. you know, those listening who have worked with coaches are probably used to the thoughtful questions and the deep listening and all of that. But is there anything else you bring into your work with clients that is just different besides just the dialogue and the conversation?

Alan47:40Sure. And I always do my best to meet the clients where they are. And so, you know, I've got some clients who have been meditating for years, probably longer than I have, and others who have never given it a second thought. When I'm doing workshops, I will often start with a short meditation video just to get everybody centered. And I have a few that I really like, or you might think about like box breathing or something along those lines. And once in a while, a client will request something like that to open a session.

Just, you know, let's get ourselves grounded. Let's put our feet on the floor, take a deep breath or two. Another thing that enters an awful lot of my sessions is the power of pause. So, you know, folks are trying to get past a certain state of mind at a critical moment. If you can picture, for example, the crucial meeting with the board of directors. And I only do this once a quarter, so I'm not practiced at it. It makes me nervous. I don't like being in front of people.

We can talk about pausing and noticing yourself and what you're experiencing in the moment and having that be an experience that's transformational. It might take a few seconds and feel like a few minutes, but is all that is necessary to get you in the right frame of mind to really be at your best before that experience unfolds. And it's happening entirely in your head and most likely nobody else will notice. So I talk about things like that with my clients fairly frequently. And one of my go-to tricks in terms of getting them to just stop and get off this potentially disastrous or destructive train of thought is the power to pause.

And I take that directly from meditation practice because to me that's what meditation is.

Ravi49:19It's almost as if with the pause, the mind finds a natural balance is the way I internalize that. Give it a, give the mind a chance and it finds like a more grounded state, like sort of water filling up an aquifer, just sort of goes there. That's how I relate to it. And yet, and I'm not. curious for you, if you can harken back to your journalist days, it seems like in society, that's not even used. And everything we watch, now I watch the news. Forget about a two-second pause.

There are six people talking. So even just having one person talk isn't enough. It's six people, let alone one person taking a pause. And so we're not necessarily seeing this behavior reinforced. In fact, we're seeing the opposite. We're seeing more information simulcast, even in the same channel. I don't know. I mean, I'm sure the power of pause was dramatic effect, I suppose. They talk about it in cinema. But I mean, why is it that you think it's not used more, given it takes no time, little time, takes actually no energy, because you're not doing anything and it has a dramatic impact.

And yet, I don't see people doing it. Yeah.

Alan50:47Well, going back to the beginning of my career since you asked, you know, dead air is anathema in television and radio. Because if you're giving them an opportunity to flip channels or find something that's more interesting, they'll take it. So we were always taught, you know, fill the spaces, fill the air time. Which is interesting because in coaching, I find it's almost the opposite is more effective. then this is something that I have to train myself on more, I find. So I think that we have a bias toward action as a society.

I think we have a bias toward just go, go, go, be active, do things, make things happen. And amazing things will happen in the white space and in the pause if you let them, but we need to create that space for it to happen. And so one of the things I've been playing with in my practice lately is talking less. And, you know, if it would seem as though, the client or coachee has finished answering the question, maybe give it a second or two more and see if anything else creeps in to fill the space that could be really interesting and juicy, which is something that does not come naturally to me.

Because if I'm done with my question and you're done with your answer, we're just going to sit here and kind of look at each other's eyes for a few seconds. It can be a little uncomfortable. It can be a little intense. But sometimes you might come up with something else and that is the aha moment that we wouldn't have gotten to if I just started talking again.

Ravi52:12Where else are you exploring as a coach? Could be learning, growing, or just exploring in your

Alan52:18practice? A number of different things come to mind. One, I tend to err on the side of support rather than challenge. So I'm challenging myself to challenge more, to push back if there's something that doesn't sound like it makes a lot of sense, or if I think a person is maybe throwing up an excuse rather than challenging themselves. Because I find it's valuable when I do it. They always get something out of the experience. And oftentimes the coach is one of the few people in their lives who will do it.

It's what Adam Grant calls the challenge network that so many of us need but don't actually have. And yet my predisposition tends to be more of oh okay, you know, to kind of be supportive and go along rather than push back. So I'm working on that. The other is, you know, as somebody who has to pay a little bit of attention from time to time to the business side of coaching the value proposition, what you can expect to get out of it, and really my own level of comfort in expressing what I think the service is worth and a lot of command as far as the market.

So that has been a constant learning. And, you know, it started with me almost, you know, coming out of coaching school and being embarrassed to ask for much of anything as far as a fee or a rate. And now, understanding a lot more about what these things are worth, what the cost of not having a coach looks like, and what my market is in terms of people who are poised to be able to use the service that I provide. So that has been a learning too.

And I know a lot of coaches struggle with that because, you know, you don't necessarily get into this work because you're good at business. You get into this work because you're good at people or good at HR or you bring something in that's kind of related as I did. So that's, that has been a learning. And And that's one of the reasons why I think I'm so fortunate to be part of communities of other coaches rather than just feeling like I have to do everything myself and make it up myself every single time.

Ravi54:12And just the last question I'd like to ask, I'm always curious what people are looking forward to. And this could be professionally or personally, what's something on the horizon that you are looking forward to?

Alan54:23I am looking forward to fall. It is my favorite season. I have lived in the D.C. area for 20 plus years and have never gotten myself used to the heat and humidity that comes our way in July and August. And to me, fall has always been associated with renewal. It's new school years, it's new semesters, new seasons, you know, new books and new shoes to get ready for all of that. My daughter's going back into the classroom for the first time in a year and a half in a few weeks here.

And I think that there's a lot of potential for just, you know, growth and human opportunity coming in the fall. So I hope that we managed to get

Ravi54:59there. Alan, it's been wonderful talking with you, learning about your transition, learning about how you support clients. If people would like to reach out and learn more about what you do, where should they go?

Alan55:12So my website is peacefuldirection.com. And I'm also on LinkedIn at Alan Heymann. And you can find me on Twitter at my first and last name as well.

Ravi55:20Great. Take care.

Alan55:22It's been a pleasure. Thank you so much.