The strange problem of outgrowing yourself

I haven’t sent out this newsletter in many months.

It wasn’t because I ran out of ideas, and it wasn’t because I was too busy.

It certainly wasn’t because I stopped caring about writing or engaging with my colleagues.

Upon reflection, I’ve become very comfortable with the one identity I’ve always had (an executive coach) and didn’t make room in my self-perception for more than that.

For over twenty years, my work has happened one conversation at a time and generally initiated by the client’s goals and challenges.

Coaching sessions, facilitating leadership team meetings and even delivering keynotes on pre-vetted topics are where I’ve felt most useful and confident and certain of the value I bring.

Writing asks something different of me. It requires me to share ideas before they’re fully formed and validated.

It asks me to start a conversation without knowing if anyone will read it, and if they will agree, disagree or even care.

So, despite wanting to write a more consistent newsletter, I made excuses and justified my hesitation to hit send on these editions by telling myself, maybe it’s not a part of who I’m supposed to be.

And trust me, as a coach, I know all about the techniques like “starting small,” or “making it easy” and am a big fan of James Clear’s Atomic Habits approach to a problem like this 🙂

Clear argues that identity follows behavior: that you become a writer by writing or a runner by running. Repeat the action consistently enough and the self-concept follows. There’s real truth to that, especially when you know specifically what you want to get better at.

But I’ve come to think his framework assumes something it doesn’t quite address. It teaches that the path to a new identity is clear once you simply start.

What it doesn’t account for is the old identity that’s still occupying the space.

You can build new habits and still find yourself feeling like you’re not doing “enough,” or that something doesn’t quite fit. And this isn’t because the habits are wrong, but because you haven’t yet loosened your grip on who you used to be.

This unexplored step isn’t about doing more, but about letting go.

Simply forcing myself to write and send more newsletters out might feel like the obvious answer, but what happens when I start to get on a roll and still feel like I’m not doing “enough?”

I believe for many of us, new habits will inform a new sense of self, but without first exploring who you want and need to “be” before “doing” more or less, you may keep chasing actions with continued restlessness.

In my case, yes I am still a coach and will continue to “do” coaching, but who I need to “be” is someone who can both advise others on their challenges and initiate learning at scale without waiting for validation or initiation from others. This is expanding my future identity but also doing the hard part of letting go of my past one when I notice it’s not fulfilling me or my potential the way it used to.

How we create our own ceilings

I’ve spent much of my career helping leaders navigate transitions, like leadership promotions, scaling new and bigger teams, and meeting expectations across wider stakeholder audiences.

What I’ve noticed about those who get stuck before or after a transition is that it’s not for lack of ability or work ethic.

They often get stuck because the identity that made them successful starts limiting them.

The executive who built a career by having all the answers suddenly needs to lead through questions.

The founder who grew a company through relentless effort now has to learn how to trust others.

The high performer discovers that they have reached a ceiling because they are great at executing on their own but have never shown whether they can drive results through leading and influencing other people.

And the thoughtful person who has spent years staying in the background realizes that visibility now matters.

None of these identities have been wrong; in fact, they’ve been so right for the past that they deceive us into believing they will serve us well forever.

Psychologist Robert Kegan, who has spent decades studying adult development, argues that growth often requires us to examine assumptions and identities we once took for granted.

And I’ve come to think that’s exactly what makes certain periods of life so uncomfortable. Because we don’t struggle to let go of what went wrong, we struggle to let go of what was going well.

Those habits and beliefs that paved the way for where we are shape our identity and even though they were choices we made (not rules imposed upon us) they feel like inarguable facts.

Looking back at my writing habits, I can now see that the gap in my publishing wasn’t a matter of poor time management or laziness, but really a struggle to let go of identifying only as a coach who responds to client needs and becoming someone who is willing to share my point of view in the absence of a request for it.

And I suspect I’m not the only person standing in that uncomfortable space between what has worked and what might be next.

Maybe you’re feeling it too.

Maybe there’s a part of your life where the strategies that once served you no longer seem to create the same results or fulfill you like they used to.

And perhaps you’ve been telling yourself you need more clarity before making a change.

But what you actually need is the courage to loosen your grip on a version of yourself that has already taken you as far as it can.

On the threshold

I renamed this newsletter to Threshold because that word captures something I couldn’t quite name until recently: the feeling of standing at the edge of what has worked, looking toward what might be next, and realizing the only thing standing in the way is your attachment to who you’ve already been.

That’s what I hope to explore with you in coming editions: the moments in life when who we’ve been meets who we need to become. And how to elegantly and intentionally manage the challenges at the threshold of future success.

Not because we have everything figured out, but because we can accept that growth requires letting go, even grieving a part of who we were, to make room for who we want to be in the next chapter.

A question to consider

What part of your identity has served you well for years, but may now be making it harder to move forward?