“I’m not sure what I want. I have a good job: it’s interesting, it pays well and I like most of my colleagues. Of course, it has its fair share of frustrations and politics, but it’s a good job. Still, I feel like something is missing: I’m not learning as much and work is not an exciting challenge anymore. Sure, my hours are reasonable and I’m well compensated, but, … Part of me thinks that I could be doing so much more, and some of my classmates seem to be doing so much better. I wonder if “future me” will regret having stayed in this comfort zone so long.”
Many of my coaching conversations start this way. The professional in front of me is clearly successful: with 15-25 years of experience, they have achieved many of the goals that they dreamed about when they started. They have worked really hard to get there: they’re smart, ambitious, dedicated and perseverant. They have delivered results and managed relationships to get things done. And now they find themselves in the house on the hill (or, if you’re mathematically inclined, at a local maximum).
Imagine an Alpine landscape: high mountains in the distance, covered in white snow, against a clear, blue sky. Further down, a verdant valley with a pristine river. And in the middle, a lofty hill, with a charming house on the top. That’s where my client is. He certainly likes the house and enjoys the landscape. But sometimes, he looks at the high mountains and feels their call. A couple of times, he decided to climb them, but as he started, he found that all the paths leaving his house went downwards first and, further down into the valley, a dense fog made it hard to see where the paths led. So he went back to his house on the hill, prepared some coffee and went back to the deck to gaze at the distant peaks.
The mountains can represent various ambitions: starting a company, a C-level role at a larger company, or a transition into PE or into the nonprofit world. My clients know that they could get there, eventually, but the goals are often hazy and the paths unclear. They understand that there will be some trade-offs to get started, in terms of salary, seniority, status, hours of work or other dimensions, and they’re willing to consider them. But they are also hesitant: by now, the stakes are higher and it’s no longer an individual decision - leaving their current comfort behind for an uncertain exciting mountain might negatively impact their families. So they stay in their house on the hill and look at the mountains.
If this resonates, you may be thinking: so, what’s the alternative?
The good news is that there are many things you can do to start the ascent and de-risk the transition. The bad news is that it will probably take longer than you expected and will require extensive research and networking. But it can be done - I’ve seen many clients reach much better destinations.
A great place to start is Herminia Ibarra’s book “Working Identity.” It prepares you to advance in three areas: people (to network with, to learn from, to be inspired by), activities (prototypes, side projects, executive education) and narrative (crafting the story that explains your past, your goals and your motivation). Interestingly, the narrative is often the hardest part, as it’s deeply connected to identity - career transitions involve leaving part of who you are behind, and there may be internal resistance to letting go of past elements that were helpful.
If several options are on the table, the Odyssey Journeys exercise in the Designing Your Life book by Bill Burnett and Dave Evans can help clarify and contextualize them. Career decisions don’t happen in a vacuum: family, health, community, financial goals, purpose, values and past experience often add constraints and slow down action, particularly in the short term. A longer term perspective (3-5 years) can unlock creativity and energy to take on the new adventure.
The journey can be exciting but will have difficult moments. While you can go it alone, it’s usually easier and more enjoyable with someone else: get a friend, a spouse, a mentor, a (former) colleague or a coach to support you in this process. They will encourage you to go through a particularly dense fog patch, get out of a blind alley and jump to the other side of the river. And when you get to the top of the mountain, you can celebrate together!
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