I wrote a couple weeks ago about the midlife reorientation, one of the most dramatic and profound transitions many of us go through as professionals and humans.

Transition is a central theme in my work with clients because startup CEOs are nearly always in the process of at least one, if not multiple, transitions, from series A CEO to series B CEO, from Partner to starting their own fund, from married to divorced, from the first half of life to the second half. These transitions, in all their forms, are the road I walk alongside my clients.

It’s common, I’ve learned, for leaders to get stuck at various points throughout a transition.

Today’s issue is about how to get yourself un-stuck.

Understanding transition challenges

I wrote last week about the midlife reorientation, one of the most dramatic and profound transitions many of us go through as professionals and humans.

Transition is a central theme in my work with clients because startup CEOs are nearly always in the process of at least one, if not multiple, transitions, from series A CEO to series B CEO, from Partner to starting their own fund, from married to divorced, from the first half of life to the second half. These transitions, in all their forms, are the road I walk alongside my clients.

In each of these transitions, I’ve noticed that leaders make things significantly harder than they need to be, because mixed in with the work one needs to do to effect meaningful change are myriad judgments about the transition itself. About its appropriateness, its feasibility, and even its morality.

When you realize you need to make a change – when you realize that the cofounder relationship isn’t working or the partnership or even the company – when you gain clarity around that, the natural first thing that happens is you judge it. And yourself. You have the realization that you have to make a change, and then immediately, as if the thoughts were joined at the hip, another part of you tells you all the reasons why changing things would never work. And how your own shortcomings are the cause of all the problems anyway. You should just knuckle up and be better, you say.

It’s normal to get stuck in this tension. To get snared by all these protective patterns, designed to preserve the (ego’s) status quo.

The way out, the grease on the skids, if you will, is something you might not expect.

The role of grace in navigating change

CEOS are used to making decisions logically. Rationally. They are used to having to justify everything to their boards or their cofounders or their investors, so before making any move they make sure they have all their ducks in a row and can explain the rationale just perfectly.

That’s appropriate for strategic decisions. But that’s not how life transitions work.

There will always be great reasons to stay exactly where you are. Listening to those reasons over your own knowing can cost you years of your life.

So what do you do, when you realize that something needs to change, but you feel stuck in the status quo for a bunch of good sounding reasons? How do you get things moving?

One word: grace.

In my work with leaders in transition, the word we most often return to is grace. Grace for where someone is in their journey, and grace that they are feeling all the things they are feeling. Complete acceptance and empathy and love toward what’s true for them, even (especially) if it doesn’t make sense. Complete appreciation and respect for their own truth, not because it’s the right answer. But because it’s their answer.

Paradoxically, in the search for reasons to push forward and make a change, when people are beating themselves up over their stuckness – their knowing that things need to change and their inability to make the move – it’s giving themselves grace for things being exactly as they are that gets things moving.

Letting go of judgement and fear

When I talk about grace with clients, they often feel two things. First, an intuitive relaxing into a partially recognized truth. And second, an acute fear that allowing themselves to feel what they feel, and to go where they’re called to go despite logical reasons and judgements not to, would lead to them losing out on the life they’ve been building.

Both of these things are true. And in holding both as true, a person has the opportunity to grow into something new. Something bigger.

If a call or even a whisper to initiate change is true for you, it is ok to pursue it for only that reason. And yes, in doing so you might lose out on what you’ve spent so much time building.

It’s scary to think of losing things that have been important to you, and reckon with the potential judgements of those around you. But it’s scarier to consider dying without ever having followed your heart. Instead holding back in the safe place of the well known, and holding on to material things you can’t take with you anyway.

In the context of the particular things you’ve been building, yes, following your inner knowing may cost you.

But in the context of your life, continuing down the same path when you know in your heart it’s not yours may cost you a great deal more.

You are on the path you’re on for any number of good reasons. And you can expect all those reasons to come up in defense of the status quo when it’s time to make a change.

But when it’s time to change, give yourself the grace to feel what you feel, and to know what you know. To trust yourself, even if it doesn’t make sense.

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The role of grace in transitions