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.

One of my clients has a long history of feeling that she is not enough. That there is nothing she can do to prove to herself and others that she is worthy.

This despite the fact that she hears from people all the time how amazing she is. That she is well-regarded by both the CEO and the president. That people have stayed with the organization just to have the chance to work on her team.

This has been an ongoing conversation, and she’s been consistently frustrated by the voice in her head that is constantly telling her all the things in her life that she is failing at.

A common challenge

Many of my clients, both men and women, struggle with a version of this story. It seems in fact, that the more successful they appear, the more they struggle with this story. And they resist giving it up. Because if they were enough, if they were satisfied, what would they do? Maybe they would just sit on the sofa and eat donuts all day!

My experience is that this doesn’t happen.

A bold experiment

Back to my client. I asked her if she wanted to do an experiment. And she is generally enthusiastic about these experiments, so she said yes.

But the experiment, in my mind at least, was a bit woo-woo, a bit out there, especially for someone who is in the middle of a high stress corporate job. I had some thoughts like, “What is she going to think of me?” and “What if this doesn’t work?” and “What if she laughs at me?” I tried by best in that moment to take action anyway, because at some deeper level, I felt the experiment to be “right.”

The experiment was this. First, to see that the voice in her head was trying to protect her. That it wasn’t about beating her up or making her feel bad. That it really wanted the best for her and was doing it in the most helpful way it could see—by providing constant reminders of the things that were left undone. By berating her, because that is what her parents had done, and because that is what she had absorbed as the best way to succeed in life.

She saw that with a little reluctance, but agreed that yes, this voice was trying to protect her, and was actually trying to help her succeed by making her feel like there was always more to do.

Talking to that voice in your head

Now the experiment begins to get a bit weird. I asked her to talk to the voice.

Some of us have talked to the voices in our head. I know I have. But it’s often from a perspective of wanting the voice to stop, of berating the voice that feels like is berating us.

I took a different approach here. I asked her to tell the voice that she appreciated the voice’s efforts, its dedication to service, and its protection and help over all these years. I asked her to really feel that appreciation. And then I asked her to ask the voice to be quiet, just for a few minutes. After all, there are other parts of herself that might want to say something. Aspects of herself that she was not as familiar with.

The voice agreed to be quiet. And then I asked her to listen with her whole body, to be open to something other than language, perhaps an image in her mind, perhaps a felt sense.

We spent some time in silence together as she was going through this process. And what happened after just a minute or two was profound.

Allowing something bigger to emerge

First, she said she had this immense sense of knowing that she was in fact, enough. More than enough, really. Amazing even. She was a bit embarrassed to tell me this.

But then, as she was telling me this, we both got an image in our heads. Of a tattoo, on her inner left wrist. Something that she could look at every day, in moments of doubt, as a reminder of this felt sense of being enough.

While I did not get a clear image of what the tattoo would look like, my client did. It was an infinity sign.

She has not gotten the tattoo, and the actual design has evolved somewhat, but in that experiment, we established that she can feel her own deep knowing that she is enough. And we now have a consistent language, and a consistent practice that we have developed together, where she can access this bigger part of herself whenever the voice threatens, well-intentioned though it is, to make her life miserable.

And every day, she draws her soon-to-be-real tattoo on her inner left wrist.

Having that reminder, and having access to that space, helps her to see things differently. It has helped her to say no to things that are not consistent with her talents and values. And to say a more focused yes when that is called for, too. She has more impact, with less stress.

When the mind slows, when the voices clear, when the panic subsides, we don’t stop doing things. But what my client says, and what my experience is, is that we often see even bigger possibilities than the ones we were considering.

When we see that we are enough, that we have always been enough, that the intelligence that is looking out through our eyes is the same intelligence behind the flowers and the trees and the stars, we can ask ourselves, with sincerity, “If not us, who? If not now, when?”

Even my own willingness to engage in this experiment was about a deep sense of knowing, and being willing to proceed despite the question that my own judgmental, afraid of being laughed at, loud-but-small voice was asking me.

That voice has been telling me not to write this piece as well, and yet here I am and here it is, emerging from a quieter presence.

The voice is always there, always trying to protect me, always trying to protect you. But there are other aspects of you, too, and some of these aspects are much, much bigger. And just like the bully who goes away when you start to ignore him, that voice can eventually quiet, too.

What calls you in your quiet moments?

Can you ignore the  voice trying to protect you and keep you small? In those moments when that voice is quiet, can you feel the bigger part of you that wants to emerge? The vast intelligence you are made of? The infinite presence looking through your eyes?

Rest in that, as often as you can, and watch your world change.

Turns out the coaching profession has a lot of things wrong about human change.

Goals are actually counterproductive.

Focusing on weaknesses? Counterproductive.

Making project plans and elaborate to-do lists? You guessed it.

What does work?

Fun. Play. Dreaming.

I’m summarizing a lot of neuroscience research here, but it turns out there are two networks in the brain that are used for very different things. And there are two different emotional states that generally go along with these networks that are also used for very different things.

When we are looking at the world through the lens of fear, or activation, or stress, we are being driven primarily by the task positive network (TPN) and the sympathetic nervous system (SNS). This system can be very helpful when we are trying to get (insert your word here) done.

When we are looking at the world through love, through openness, through possibility, through connection, we are primarily in the default mode network (DFN, our sense of a self) and the parasympathetic nervous system (PNS). This system helps us rest, recover, connect, and contemplate.

When you are working furiously to meet a deadline, you are in the SNS and the TPN. When you take a break, go for a walk in the park, and have that sudden insight of how to save 10 steps and do the project better, you are in the DFN and the PNS.

When we go about trying to make changes, our first instinct is to think about our weaknesses and create a project plan to overcome them. We use the TPN and SNS to try to wrestle the problem to the ground.

It’s a reasonable instinct, and not surprising given how much of our lives are typically about doing. But while the TPN and SNS are great at focus, that focus is accomplished by shutting out the possibility of thinking about things differently. In other words, by using these systems to try to change, we shut down the very possibility of the change we are attempting!

Have you ever tried to lose weight by counting calories and noticed that all you think about is cheesecake?

That’s the TPN and the SNS, trying to use your existing wiring to get to your goal as efficiently as possible and, by the way, failing miserably.

But if you dream of an image of who you want to be, and then ask yourself “what would that person do in this moment?” you have a better chance of tricking the system.

If you play Rich Litvin’s “perfect system” game, where you make an exaggerated point around exactly how you created the system that creates your stress, overwhelm, or whatever else is in your way, you have a better chance of tricking the system.

And dreaming and playing are easier and more fun, too.

I’ve decided that every Friday is going to be my dream day.

To dream big about who I want to be, what I want my business to be, who I want to work with as clients and colleagues.

To dream big about the world that I want to create, where more and more leaders create companies where the best people and ideas thrive, where more and more people bring their full selves to work, where fewer and fewer people they have to make compromises to make money.

To dream big about a world in which we take care of our workers, our customers, our suppliers, and the environment, rather than trying to extract maximum shareholder returns (and employee well-being) in the short run and let everyone else fend for themselves.

To dream big, and then to take tiny sustainable steps toward that creating that world.

And to have fun doing all that.

I work with so many leaders who have “achieved” their whole careers and now are trying to step off that hamster wheel because the path has become the obstacle. They see what they have given up with their relationships and their health. They see that they have built a success that felt great in the first few decades of their career but now feels empty. They crave a meaning that is missing and they see that what they are doing is no longer working for them. They know the next step is to step away (at least from a lot of the day-to-day drama) but they don’t know how. One of my clients, a CEO with 100 employees, calls it being stuck between being a small company and a big company, with his day-to-day involvement being the main obstacle.

He doesn’t see (yet) how to step away so his company can grow. But as we dream more and more, as we play, as we begin to take the whole project a lot less seriously, the chances of him having that insight become a lot higher.

Fun, play, dreaming can feel so trivial sometimes.

But it turns out if you want to change, they might be the most important thing you can do.

 

I used to write about things like big visions and impossible futures.

And while I still believe in both, my experience is that many people tune out when I write that way. It feels too daunting. Life is already hard, and now you’re asking me to dream bigger?

Maybe my “impossible future” is that I want things to be just a little bit easier. A little less overwhelming.

That’s where “What if?” comes in.

My experiment with “What if?”

My experiment with “What if?” is actually a pretty big one. (At least if feels big to me.)

“What if I could create an abundant life in a beautiful place doing work that I am passionate about with people I love?”

Your “What if?” might involve moving across the company and changing careers at age 50 (as mine did).

It might be bigger. It might be smaller.

But “What if?” conveys a sense of play that seems to work a lot better than planning.

The folly of five year plans

For one period of my life, early in my career, I would wake up every morning and think about my five year plan—where I wanted to be, what title I wanted, how much I was going to be making, and so on.

Every morning.

And it only took me about fifteen years to figure out that I had no idea what was going to happen in five years. When I was a partner at a global consulting firm, I had eight jobs in 15 years. Sometimes, I left home one day with one job and came home with another. I planned for very few of those jobs. One day I actually came home with the news that we were going to be moving across the country.

What’s that quote? “People plan and God laughs?” Somehow, the universe always seems to provide what is needed, yet it does so in ways that I could never predict. (See my “what if” above.)

“You don’t need to know how.”

I recently had an insight that felt, in my bones, one hundred percent true, while at the same time going completely counter to my past tendency to come up with five-year plans every morning.

You see, I’ve felt compelled to write, to share, to dive deeper and deeper into these topics of how we find our way in the world, how we become more human, how we lead from a place of authenticity and even love.

And yet there are days where I send email after email to total strangers and have no idea what to do next.

There is still that muscle in me, still that tendency, to want to know what to do. To want to make sure that I am “working hard,” so that I can “earn” this thing called “success.” I want know how things are going to turn out and when I am going to have “made it” down this new path, this “what if” experiment that, seemingly at the universe’s urging, I created for myself.

But the insight was this—

“You don’t need to know how.”

I don’t need to know how this is all going to come together. And, when I can trust, there is great peace in this.

Your invitation to the universe

I believe that this system that we are all part of is perfect at bringing us exactly what we need exactly when we need it. And when I look at the biggest gifts in my life, I had no idea when or in what form it would come. I did what I felt I was supposed to do, and then the universe, time after time, did its part.

“What if?” is your invitation to the universe.

“What if?” is the invitation that every one of my clients has made.

“What if I can make more money working for an organization with a mission that inspires me?”

“What if I can create new line of business while my employees take over the existing one?”

“What if I can be the leader my organization needs?”

“What if my team can be as committed as I am?”

While the universe never seems to answer in exactly the way that I (or my clients) expect, it does always seem to give us exactly what we need.

And if you’d like a guide as you live out your version of this mystery, I’m happy to help you in any way I can.