10 Years In: What I’ve Learned From a Decade of Running Pivot Journeys
Ten years ago this month, I walked away from my last traditional job and committed fully to building Pivot Journeys. It’s amazing how fast 10 years go by.
I wanted to mark the occasion and share some of my top reflections with you. But first, some numbers:
419 individuals served through 1:1 coaching
3,100 coaching sessions
2 part-time Pivot coaches hired to support the work - Kate joining 6 years ago, and Smita 2 years ago.
57 public workshops (plus countless more for external groups) + 31 Career Navigation Roundtables, reaching thousands of professionals
26 partner organizations for retreats, programs, and workshops
70% of our individual clients come from referrals
But what have I seen and learned about careers and myself over the years?
So many things, I could write a book. But I’ll try to summarize just the top few that I think would interest people most:
People are wildly, beautifully different — in ways that stretch me every day.
It feels silly to say that people are different — of course we all know that. But it’s those differences that stretch me as a coach in ways that are both challenging and genuinely fun.
In a three-hour window this week, I worked with two clients whose approach to the exact same task could not have been more different.
At 9am, I spoke with a client about his LinkedIn profile for the third week in a row. He had watched our videos and viewed our templates, and still wanted more time to research, talk through the strategy, and figure out how it aligned with his values. With him, my role was to gently push toward execution — to help him get something on paper and trust that we could refine it together.
Two hours later, I met with a client who had the opposite instinct. She didn’t want to talk it through and felt comfortable following her gut on what felt natural to write. My style had to take a 180-degree turn to slow her down and get her to see she that hadn’t considered the big picture strategy, and didn’t have a sense as to what her career narrative should be for her intended audience. At that moment, I was a coach, but also an advisor, helping her pause before hitting publish. (What’s wild is that these two clients actually share some of the same CliftonStrengths talents — people are complex.)
All the research tells us that great leaders tailor their style to the person in front of them. What I didn’t fully anticipate was how much constant flexing that would require, hour to hour. It’s a real mental tax that comes with deep 1:1 work. It can be tiring. But it’s also one of the most fascinating parts of this job. No one is better or worse. Just different. And I love getting to meet people exactly where they are.
What once triggered my imposter syndrome has become the most rewarding part of my work.
In January 2018, I started coaching a client who worked in a job I knew hardly anything about - global operations for a huge bank. I was so nervous I wasn’t going to be able to help him figure out where he wanted to go in his career. Even midway through our work I wondered if I was really helping him, and questioned whether I should just stick to working with people in industries/roles I knew a ton about. But he landed in a great stretch role that led him to a few other positions where he’s reached a high level of success. When we started working together again this year to map the next chapter of his career I had zero anxiety or worry about supporting him.
Now, I LOVE when I get to work with someone who does something I don’t know much about! It’s just FUN to learn all about different types of jobs. Arctic science research, fashion design, high-level military operations, biotech research, cable sports production, talent managers for writers, comedians, and countless other types of work that I would never have learned about if I had said no to working with that guy. (Thanks for taking a chance on me in 2018, Mike!)
I am so grateful for the breadth of careers I’ve gotten to learn about and the personal stories are what make it the most fun.
Finding the balance between encouraging big swings and being honest about what’s likely is really tricky.
Walking the tightrope between encouraging people to dream big and helping them understand what’s realistically possible, given their constraints, is challenging.
I want people to go after work that feels more aligned and exciting than what they’re doing now. I’ve seen enough surprising and awesome outcomes over the years to know that people can execute big career changes that are life-changing for them. At the same time, I’ve also seen how timing, market conditions, compensation needs, existing experience, grit, perseverance, and plain old luck! shape what doors actually open for folks.
That tension shows up most clearly when someone wants to make a significant leap — for example, moving from an account management role at a tech company into a Chief of Staff role at a nonprofit, or a program officer role at a foundation. I get the appeal - those roles sound meaningful, influential, and special. And many people do have transferable skills for lots of types of work!
Side note: If I had a nickel for everyone who says they think - and think they’d be great at being - a Chief of Staff... And the runner up of interest for the most folks: working at a foundation.
Pulling off what I call a ‘Double Pivot’ (changing your job title & function + your industry) is doable - we’ve seen many people do it successfully, but a) there are some pivots that are just harder because of the supply/demand of the job market, b) they take a lot of time and perseverance -- and therefore, they are not the norm. My coaches and I don’t screen for talent. Or resilience. Or someone’s network to know if they’ll have someone who will open an unexpected door. So it’s impossible to predict who will get the break.
Part of my job is to level with people without crushing their spirit because pretending otherwise doesn’t actually serve the person I’m coaching.
What we can do is help people understand the terrain — where the path of least resistance might be, what tradeoffs they’re making, and what kind of effort and patience is likely required. (I’ve found on exploratory calls (aka sales calls) that I spend more and more time setting expectations with folks so they really know what’s ahead if they want to make a big change.)
Learning how to hold that balance — encouraging possibility while being honest about probability — has been one of the more challenging parts of this work. And it’s something I still think about constantly: how to support ambition without selling false certainty, and how to offer realism without extinguishing hope. It’s even more challenging in today’s job market.
The hardest part for me has been saying no and setting boundaries.
When people ask me what the hardest part of my work is, I think they expect me to say ‘business development’ or ‘marketing and getting clients’. In the beginning, yes, that probably was the most difficult part of my work. But as years went by, it became saying no and setting boundaries confidently.
What does this look like? It looks like telling someone who is anxious to get started that I don’t have openings for 4 weeks. It looks like enforcing a late fee charge when someone reschedules a session the day of. It looks like saying no when a new client wants to schedule a session on a day I had planned not to work. These types of things happen every week and without a doubt, dealing with things like this is the hardest part of my work. (Yes, I’m an enneagram 2.)
And yet — boundaries are the only way the work stays sustainable.
It took me years to learn that saying no doesn’t make me mean or difficult. It makes the work better because it helps me show up better for the clients I serve. But that doesn’t mean it’s not the most difficult thing I still struggle with.
You get to redefine what success looks like throughout your career — and it changes.
I work with so many clients on their own definitions of success, and somewhere along the way, I had to do that for myself too. Sometimes I meet with other business owners and feel so much less successful because I don’t have a coaching practice of 10 coaches, or don’t make $500,000 a year. When that happens, I have to remind myself what success looks like for me.
In years 0–5, I loved taking the subway home from my office at 8:30pm, walking by the NY Stock Exchange, passing the Fearless Girl, and feeling like I was building a business I was deeply excited about. Getting home at 9pm felt rewarding — like I had done great work. But now? Nope. It’s changed.
I take a ton of time off (an embarrassing amount, truly). I get to be choosy about the clients I take on so the fit is excellent. And thankfully, I still don’t get the Sunday scaries (though I wouldn’t say no to another day off).
Nothing about this later definition would have made sense to me in year one. When you know what success feels like to you (and it’s truly your definition) it’s so sweet and satisfying to build a life that reflects it. I feel enormously grateful for that. I hope it continues.
No one has it all figured out — including me.
Our world changes too quickly, and careers shift too often, for anyone to have a foolproof plan. And I’m no exception. There are days I wonder what it would be like to go back to a big company with hundreds of coworkers, and days I question what I want my work to look like in 5 years, or how to handle challenges in my own work.
What I’ve seen — in myself and in the people I coach — is that the happiest, most grounded folks treat their careers like a journey they’re genuinely curious about. They’re engaged in the process. They wonder what the next chapter might hold without needing the cliff notes or a guaranteed ending. They show up with a mix of adaptability, strategy, and strong executing abilities, knowing the story will keep unfolding in ways they can’t fully predict. And that curiosity makes the whole thing a lot more satisfying.