I recently spoke with Tim Alison on his Screw the Naysayers podcast. Tim focuses on leaders who have defied conventional wisdom, who have taken a different path, and I was honored to be included.

We spoke at length not only about my leaving the corporate world, but also about building a business as an executive coach, and about the ultimate futility of external goals in defining success.

Please enjoy this episode here.

I recently had the pleasure of appearing on Kyle Weckerly’s Career Challenges Podcast, talking about the importance of self-awareness as a gateway to change.

If you want to change something, you have to be aware of it. And there are a lot of ways to cultivate that awareness, of your thoughts, of emotions, of sensations in your body, of triggers that show up for you. In that way, leadership is self leadership before true leadership of others can take place.

My experience is that without some kind of formal awareness practice, it is difficult to make major changes. If someone else sees something in us, it is often quite difficult to take action on it, even when we agree with it. But when the insight is ours, seeing new possibilities, making new choices, and taking new actions becomes much easier. And in my experience, that kind of insight shows up much more frequently when there’s a practice supporting it.

Kyle and I talked about all of that and more, including some client stories, for almost an hour. Have a listen here.

I often find myself thinking about the next thing, thinking about how far I have to go, rather than celebrating how far I’ve come. And it feels self-aggrandizing even to take a moment to celebrate something I’ve accomplished.

I take time with my clients to celebrate their accomplishments, so I’m going to take time to celebrate an accomplishment of mine here. As Labor Day is often considered the end of summer, I’m going to celebrate a challenge I took on in June, and tell you a few surprising things I learned.

In early June, I decided to learn to swim better. And I set a goal of swimming a mile. That’s 64 lengths of a 25 meter pool without stopping.

I’ve had a difficult history with swimming. I was five the first time I had a swim lesson. At the end of the lesson we were asked to jump off the diving board holding on to a pole. I was terrified and refused. No more lessons for me for more than a decade. I took lessons at the same YMCA so I could swim enough to pass PE in high school. But I hated every minute.

I returned to swimming in my late thirties when I decided I wanted to do a triathlon. I learned about something called Total Immersion Swimming (you can Google Tim Ferris taking about it if you’re curious) that was supposed to be a lot easier than traditional swimming. I even took a weekend workshop on the method and got to the point where I could (finally) swim a length of the pool comfortably. Sometimes I could even make it two lengths. I started going to another Y, in Bethesda, Maryland, to try to get better. But I don’t think I ever got past 4 lengths. And I quit, again. The triathlon never happened.

Now I’m 54 and returning to swimming (and a potential triathlon?) for a third time. And for the first time I’m really loving not only the sense of being and moving in the water, but also the process of learning. While there’s a lot of discomfort at the beginning, there’s also rapid progress.

I started swimming again at the local pool in June. My first workout, I swam for a total of 8 minutes. The most I could swim at a time was two lengths of a 25 meter pool. On August 28, less than three months later, I swam a mile in one workout, and the first 38 lengths of the pool were without any breaks. I have not met my goal of swimming a mile nonstop yet, but I have come a long way.

(I started to swim in a cloudy lake over the weekend and realized I now have a whole new set of mental challenges to overcome if I want to do a triathlon, which has open water swimming. I made it about twenty yards and when I realized I was literally in over my head, I panicked and turned back.)

The value of new challenges

This is one of the reasons I like to take on new challenges. This is one of the reasons I like my clients to take on new challenges. To have the feeling of discomfort at the beginning and to also the feel the rush of progress that happens when you have pushed through that discomfort. The confidence that comes from succeeding at new challenges seems to transfer to other life areas, too.

It’s a good way to experience beginner’s mind, and to practice the acceptance of not being an expert. I can have another swimmer blow past me in the next lane and admire that person rather than beat myself up (at least more than I used to!). This admiration of others and kindness to myself is new for me.

There’s another way that I’ve been surprised, too. In some important ways, learning to swim and learning to be a better leader are actually quite similar.

Change is uncomfortable. When you’re engaged in a physical pursuit like swimming you clearly feel discomfort in making your body do things that it’s not used to. But most people don’t see that leadership is an embodied practice, too. If you’re trying to be different as a leader, you will feel discomfort in your body. That’s actually the only place that discomfort can show up. You know on some level that what you are doing is different. Your body automatically resists new things by making you uncomfortable. It’s trying to protect you! You might feel a flutter in your stomach, a tightness in your chest or throat, or something other physical sensations that indicate you are outside of your comfort zone. These sensations will change as you get more and more comfortable with your new way of being.

Like any journey of mastery, no matter where you start from, you can always improve. I’ve talked to leaders, often longtime ones, who are always learning, and my swim coach says he’s still learning after swimming for more than 30 years. There’s a humility and respect for the process that seem to be necessary, and present both in the best and those aspiring to be the best.

The more awareness you have, the more rapidly you will progress. This includes getting feedback from others. A trusted observer is essential to progress, especially one who has been through the same journey you are going through. You can read about things but until you have a coach looking at you or you see yourself on video you might not have a clear perspective on how you are actually doing things and how that compares with what you’re trying to do. A change as simple as where you put your hands with you push off the wall can take seconds off your lap time. A change in how you hold your body as you ask for feedback can make a huge difference, too.

A lot of the fundamentals are counterintuitive

Three areas of swimming struck me has having very distinct parallels to leadership, in that the thing that works is actually opposite of what most people instinctively try.

The quieter you are, the more effective you will be. In swimming, you see a lot of beginners kicking and splashing as hard as they can as they move up the pool. Like me, they are exhausted by the time they have completed a length or two. But look at an expert, especially an expert distance swimmer, and you will see very little splash. You will hear very little noise. You barely see their heads when they breathe.

What does this look like in leadership? We all know the classic leader who pounds his (and it is almost always a he) fist on the podium, exhorting his people to greater effort. Whoever came up with that t-shirt that says, “The beatings will continue until morale improves” was thinking of this kind of leader. This can work. For a little while.

But the most effective leaders over the long term are often the ones who don’t make a fuss. Who rarely raise their voices. They focus on connecting with their people rather than being in the spotlight. And not only do their people take ownership, the leader is happy to give them credit for their success.

It’s more effective to reduce resistance than it is to increase effort. In swimming, you see a lot of people kicking a lot at first. This is a terrible way to move through the water. Generally speaking, the reason that people are kicking is that they have their heads too high—they want to have access to air! They have to kick to stay afloat because their heads are so far out of the water that it pushes their legs down. But when they lower their heads, when they rotate to the air instead of lifting, their legs magically pop to the surface. And they discover that gliding is a lot easier (and faster!) than kicking.

Lowering resistance is something that you used to see in Washington. Back when I was a child, there were lawmakers who worked diligently, across the aisle, seeing how to get a deal done, seeing how they could improve things for the most people. They lowered the resistance of those on the other side by seeing what could work for everyone. These days, a willingness to compromise is often seen as a negative. The effort is there—politicians on both sides tirelessly declare that they have a monopoly on truth and pledge to their base that their view will prevail—but resistance to actual progress (however defined) has increased rather than decreased.

The folks who get things done, whether in politics or business, are often the ones who are working with those with differently perspectives to see what is possible. They are willing to move a little at a time toward their goal rather than making an all-or-nothing effort and failing over and over. And because of that, they go a lot further over time.

You can control the commitment, and the goal, but not the timing. I decided to commit to learning to swim better. I set a specific goal of swimming a mile at the pool. At that point, though, from what I can tell, I was no longer in control.

When I’m committed to a goal, I usually meet it. But I often have no idea how long it will take to meet that goal, especially if it’s something I’ve never done before. I could not have told you if it would take a month, or three months, or two years to get to the point where I could swim a mile. And while I am close to swimming a mile without stopping, the local pool is now closed and I will have to move to an indoor pool in the next town, which will not open for winter for another week. Sometimes things happen that are outside of our control.

In swimming, when I got that first rush of progress I started looking for triathlons that I could do this year. I even found one in southern Utah at the end of October. But my coach pointed out that the process is supposed to be fun! How easy it is to forget that! It was a big learning for me to realize that I actually wanted to enjoy the journey, and that I would enjoy it more if I thought about a triathlon next summer rather than a couple of months from now.

In business, you see deadline-based goals all the time. In fact, Wall Street often demands them. But, especially when it is something that hasn’t been done before, it’s almost impossible to predict timing. I had all kinds of overachiever ideas around how quickly I could build my business. My ego was strong enough that I decided that I would take the time it typically takes a successful coach to establish their practice and halve it. And then I beat myself up for not meeting that. Being hard on myself didn’t do anything other than make me feel bad. Things went a lot better when I accepting that I could only control my commitment, my goal, and the actions I was taking toward it. Not the results of those actions or the growth rate of the business.

Making the commitment

Have you beat yourself up for not being able to change? Maybe you want a different role, or to take your business to the next level. If you’re clear on your goal, commit to it! But don’t get too attached to how or when you get results. You’re doing your best, and learning to enjoy the process of change is a practice in and of itself. You may find, as I have, that life has an even better plan for you than you do. And that you will be pleasantly surprised from what you learn along the way.

This week has been a week of reflection, of anniversaries, of mourning, and of gratitude.

In Memory of Doug Silsbee

On July 30, 2018, one year ago this week, my coach and mentor Doug Silsbee passed after an intense battle with lung cancer. Doug had never smoked a day in his life, and at the age of 64 he was far too young. Yet the ripples that he made through his passion for the study of coaching, through the three books that he wrote, and the hundreds of coaches he trained will be felt for a long time. While I continue to mourn his passing, I am also filled with gratitude that I got to know him, that I got to work with him, and that I was able to witness and be inspired by his life journey and even by the conscious way that he faced illness and death.

A different kind of passing

On August 2, 2016, three years ago today, I was let go from my position at Fidelity Investments. And while things look very different today, it hit me hard at the time.

Suddenly, I was in a land with no name. For almost thirty years I had worked at large well-known firms in employee benefits and health care. My identity was tied up in those firms, and often, in being their public face, both in Washington, DC, where I worked with legislators and regulators on complex issues, and with clients, where I created strategies to help employees more effectively address their financial challenges.

And now that was gone.

For the rest of August, I was simply trying to find another role within the firm, so that I could stay at Fidelity and keep my benefits. But it quickly became apparent that was not going to happen. Then my last day came and with it a strange mix of panic and certainty.

On one level, I had this deep certainty that I was not going back to a big company. That the time had come to go out on my own, to just be Jeff, not “Jeff from [fill in name of well known employer here].” But how exactly to do that seemed overwhelming.

I had thought about executive coaching for a long time. I had even set up a website when I was at another employer (got into a bit of trouble for that…). But in a world in which 90 percent of coaches make less than $20,000 a year, the prospect seemed intimidating.

I had a couple of ideas for consulting businesses, but when I test marketed them they went nowhere. One of the people I was testing my ideas with said, “I thought you were passionate about coaching.” While big firms were hiring employees, no one was looking for consulting work. And then I got an email about a coaching intensive from someone I had been following for a while. Hmm.

The journey to this point

Everything seemed to be pointing me toward coaching so I plunged in. It was hard. It was messy. I had no idea what I was doing some days. I had bouts of sleeplessness and lots of difficult conversations with my wife. But three years later, I have a business that is working, clients who I love working with, and I get to live in a spectacularly beautiful place. I wouldn’t trade it for anything, and yet three years ago I had no idea it was even possible.

I also celebrated a major victory with one of my clients this week. I told her about my anniversary and asked her about what she was doing three years ago. We reflected, with incredible gratitude, how much each of our lives has changed and how intertwined in each other’s success we have been.

Here’s a brief summary of both our journeys, and some of the things I have learned along the way.

August 2016. I was fired. Coincidentally, my wife had been going to a small mountain town Carbondale, Colorado (about 30 miles from Aspen, on the Western Slope of the Rocky Mountains) to do yoga for several years and had brought me to visit on July 4 after we had been at a family wedding in Colorado Springs. When she asked me what I thought, I said something I will remember the rest of my life. “It’s beautiful. I can absolutely see living here someday. But this place is three hours from a major airport and I’m in Boston every other week. As long as I’m at Fidelity, this could never work.” One month later I got my notice and a nice severance package. Hmm.

My client had topped out in her role at a big consulting firm. She loved the team she managed but had a difficult relationship with her boss. She had thought about leaving but had no idea what she might do elsewhere and was sure she would have to take a pay cut. It seemed like she was stuck.

August 2017. At this point I had opened a coaching business and had moved from Washington, DC, to Carbondale. Between the severance that I got from Fidelity and downsizing our house, we could generate a nest egg to fund the new business. One coincidence after another seemed to keep things in motion. I hired my own coach and later decided to start coach training with Doug Silsbee. I spent hundreds, perhaps thousands, of hours training and practicing my new craft and telling people about what I was doing and who (and how) I could help. In perhaps the most auspicious event of the whole move process, we had found “the” house in Carbondale and put an offer on it but needed to close quickly. We hadn’t put our house on the market in Bethesda, MD, a solidly liberal DC suburb. This was in the months after the Trump election, when Republicans were moving in and Democrats were moving out. I was deeply concerned, and yet we sold our house for five days, for cash.

We needed one offer, and we got it.

My client spent that year struggling. We had worked together at one point and she knew what I was up to. She became my first paying client in June of 2017 and we got to work on improving her relationship with her boss so that she could begin to network and explore. She began to see some possibilities.

August 2018. I was now certified as a Presence-Based Coach and had had many more coaching and business development conversations, but only had two new clients to show for it. It seemed like things were moving in the right direction, but they were moving much more slowly than I had been hoped. My client was accomplishing her goals more quickly. She had left her firm for a dream job with a mature health care startup whose mission resonated and whose leadership team inspired. She was making more and on top of it had a generous equity package.

August 2019. Suddenly it seemed like the business was viable. I had always wanted to work with CEOs and at first I thought it was a pipe dream. But then one hired me. And then another. And then another. Today I have a solid book and a rapidly growing base of clients—CEOs, business owners, and senior leaders at bigger companies. I’m not where I want to be yet financially. It has not gone as quickly as I would have liked. But it has come, and after a couple of really slow years financially, I’m on track to match my old base salary by the end of this year.

My client has blossomed, too. She just celebrated a year at her new position and we just finished another six months of working together and are heading into six more. While she has always been great at knowing what she wants and getting it, she always struggled with overwhelm, with a sense of not being enough. And lately I’ve seen her make incredible strides. Her new challenge is to stay centered and present managing an organization that is much larger than the one she started with. She has been giving two new groups of people to manage just in the last week. And one person even threatened to leave unless he could report to her. I, her boss, the president, and the CEO are amazed at the growth that we have seen in her in such a short time.

The lessons and themes

So what have I learned from all of this? Here are a few themes I see so far.

Identity is everything

When I lost my job I lost my identity, too, and I didn’t just “become” a coach a week later. I remember the first time I was at a party and my wife introduced me to one of her influential friends as a coach. I had a panic attack just like the ones I used to struggle with twenty-five years ago. I’m sure I didn’t come across very well with sweat pouring down my face, looking for an escape route to the nearest restroom so I could towel off.

I had to grow into that new identity, just as my client had to grow into hers. And I yet had to “be” a coach before people would hire me as a coach. That might be the biggest trick in all of this, the precursive faith that you can do something before you have actually done it.

Burn the boats if you must

In 1519, Hernan Cortes set sail from Mexico to conquer Spain. It was an arduous journey and when he landed his men were weary, and hopeful of returning home to their old lives. In what has now become legend, once the ships landed, Cortes ordered his men to burn them.

Turning back, going home, was no longer an option.

The standard advice when starting a new business is to do it as a “side hustle.” To develop a couple of clients and a level of income before quitting the day job.

That never worked for me. But when I had no other options, when I had to make it work, that was when I become motivated. That was when I became focused.

I wasn’t reckless. I had ample savings to cushion a year or more of making no money in the new business. I had retirement savings as a backup if I needed it. But I did find that doing something 40 or more hours a week was a lot more fruitful than doing it ten. And I know people who have gone into debt, or spent all their retirement money, or both, and the resulting panic isn’t good for business development. So there’s a balance.

For my client, she had loved her job but the business had changed and no longer required her special magic. The founder, the most inspirational boss she had ever had, had tragically passed away, and the new boss was not a fit for her.

For different reasons, she couldn’t go home again either. Everything had changed. She had to find a new way. And she has.

It will seem like nothing is happening

There’s a lot of foundational work that has to happen before you begin to have success. For me, it was not only training, but practice, and seeing myself as a coach, and beginning to build an identity in which I could confidently help the people that I wanted to help. There are a lot of distractions along the way. There are a lot of shiny objects. There are a lot of people who want to tell you that Facebook ads or SEO or some other magic solution will allow you to build a business without actually talking to people.

That may be true for some businesses. But in coaching, I have to know and trust and be willing to be vulnerable with the person I want to coach, and they have to know and trust and be willing to vulnerable with me.

Sometimes it takes a year or more of conversation before someone hires me. They have to both trust me and face a situation where they need help, and that can take time. But three years in, I have a lot more of those relationships to draw upon, and a much clearer identity of who I am and how I help. I know of no shortcut to get there. Suddenly, the revenue turned upward, and I wanted to think that I could have skipped the years of struggle. But it was building the very foundation of the success I am now having.

My client spent six months networking and thinking about what she wanted before she entertained any job offers. She spent another year (a lifetime, really) working with her stories of overwhelm and inadequacy. She’s totally different leader today, and yet all that work was foundational. Again, no shortcuts.

Watch the leading indicators (not the cash flow)

One of my coaches, Rich Litvin, is a big proponent of this. If you are connecting with the right people, if you are having the right conversations, the business will come. But you have to be prepared for this, to see it as a feature, not a problem.

There will be fewer ups than downs

I have more months where I sign no new business than months where I do. Cash flow is lumpy, but as long as effort is consistent, things seem to work out.

Be willing to be surprised

There’s a fine balance between being focused and being open. Of watching the indicators along the way. Of going with the flow. One thing I noticed is that I was more successful when I worked less. That I was more present when I got more exercise. I’m 20 pounds lighter than when I started this journey, and all came off in the last six months. It just seemed to emerge, and I’m grateful for it.

There is no there

A great myth of all small business (of life, really) is that there will be a point where you have “arrived,” where you can coast, where the business takes care of itself. But my experience is that even when things are going well, there is more you want to do. You find yourself drawn to different people, or different ways of doing business, or different products or services.

This, to me, is actually the most exciting aspect of the journey. The fact that it is always fresh, always different.

This is true for my client, too. Our conversations are never the same. The role continues to evolve. And she continues to feel challenged and grow.

Celebrate the successes

There is a coaching move called “taking in the good” that is incredibly valuable. The idea is that we so often get caught up in what we haven’t done that we don’t reflect on what we have accomplished. But when we do, when we sit with what we have done and the new identity that we have become, we strengthen all those new connections and more deeply embody the changes we are making.

I did that with my client this week. I wanted her to see and feel good about everything that she has done, and the new leader she has become.

And a lot of the reason I wrote this post was to do the same for me. The journey has been difficult at times, but with the help I have had from mentors, from coaches, and especially from my wife (our anniversary is August 4), it is something I want to celebrate. I hope this post has also been helpful for you, both in celebrating your successes, and perhaps, in helping to inspire you to create that thing that has been calling you.