Ep 6: From Wall Street to Chocolate
Caroline Witmer, co-founder of Tuck Shop chocolate, discusses her journey of letting go of the 'expected' path to do something fun.
In this Substack:
An introduction to this 30 minute podcast
My deeper analysis as a coach on why Caroline is so aligned and thriving
Caroline’s New York City recommendations
Meet Caroline Witmer
Caroline Witmer is the co-founder of Tuck Shop, handcrafted chocolate that captures the spirit of your happy place.
Do you ever feel like the career you built is the one you thought you wanted - but then you wake up one day and realize it’s no longer clicking?
That’s where Caroline Witmer found herself. Brown grad. Columbia MBA. Wealth management. Private equity. She’d ticked all the boxes, jumped from chapter to chapter with ease, externally she was ‘crushing it’… but never looking inside to ask herself, are you happy? Is this really what you want?
In this episode of Character, I sit down with Caroline—who’s actually a former coaching client of mine—to talk about her journey from finance to founding Tuck Shop, a handcrafted chocolate company capturing the spirit of your happy place.
This is an episode about giving yourself permission to get off the hamster wheel even when you don’t know what’s next. It’s about learning to hold everything a little bit looser when you’ve historically always been the person who checks all the boxes.
Caroline shares how she went from living for external praise to trusting her own compass. How she started a business while pregnant with baby number two. And how she’s building something meaningful while raising three kids under four without the pressure and intensity that colored her career in finance.
If you’ve ever felt stuck on a path that looks right but feels wrong, this conversation will give you permission to explore what’s actually calling you.
In this honest conversation about career change and building a life with Character, we explore:
How do you know when it’s time to leave a career that looks good on paper?
Letting go of other people’s opinions.
Giving yourself permission to play.
Building a business while raising three girls under four.
What it takes to let go of the pressure and hold things looser.
4 Coaching Lessons From My Conversation with Caroline
Lesson 1: Caroline let go of the ‘work has to be serious’ belief and ‘black and white’ thinking
“Work doesn’t have to be so serious, so black and white, but that was certainly my early idea of what work was… like you need to hit this mark so you can go to the next thing to the next thing. And where I am now is continuing to remind myself that life has many chapters. Today’s chapter is going to be different than tomorrow’s and yesterday’s.”
So many of my career coaching clients meet me in this place. They absorbed a belief growing up that work needs to be serious and follow a predictable path. And that if you fall of this path it means you’ve somehow messed up. Personally, the more I’ve fallen off the path I expected, the more I’ve been able to connect to myself and create a career and life that’s uniquely my own and thus deeply satisfying.
Starting Tuck Shop required Caroline to do just this. She had to give herself permission to play and to follow the germ of an idea that made her feel light inside. By using this as her compass not only has she started a business, she’s found new parts of herself - including a realization that she’s actually quite creative. She’s been able to have fun and live a life more in sync with her values and priorities alongside building something fun.
Lesson 2: Caroline didn’t ignore her feelings
“I’m lucky because I don’t really ignore [my feelings]. Once I notice them I’m gonna stop and listen.”
Caroline discusses how one of the biggest realizations she now has as she looks back on the first decade or so of her career is how she wasn’t even giving herself the space to notice her feelings. She was heads down, go go go. But when they finally pushed their way to the surface after a yoga session and she realized that things no longer felt right in her career, she didn’t ignore them. She discussed them with her friend. And her friend referred her to a coach (me!).
Your feelings need to work in concert with your intellect to help you find your way to your most aligned path. Your body will always tell you when you’re not in the right place. You have to create the space to listen - feelings are often gentle at the start - and then you want to honor their messages by acting on them with intention.
Lesson 3: Caroline is slowing down and focusing on the fundamentals
“We’re laying brick right now. We’re building the foundation of a business and in one to two years we’re both going to look up and our kids are going to be a little bit older and how happy are we going to be that there’s already an amazing foundation to something that we could potentially grow and grow and grow.”
As opposed to her early career when she prioritized speed - putting pressure on herself to get to that next chapter as quickly as possible - Caroline is allowing herself to slow down and really just focus on the fundamentals. So often what I see in my career coaching clients is that people are rushing to get to that next step. It’s an approach I’ve morbidly coined “Rushing Roulette”. When we rush we get out of alignment, because the priority is speed instead of fit; clients end up in roles that aren’t right because they’ve just taken the first thing that came in instead of waiting for the right thing. In the entrepreneurial game, rushing can mean that the business isn’t set up to scale when the moment is right. This is what Caroline is focused on getting right.
Lesson 4: Caroline is holding everything a little bit looser.
“Hold it all a little bit looser. There’s no just one perfect outcome. Maybe option A didn’t work out but Option B, C, D, they might be better than option A, you just haven’t even allowed yourself to look at them yet. I took myself too seriously. And I’m glad that that got me to where it got me, but it was stressful, and it didn’t necessarily need to always be so stressful.”
When we hold things tightly we end up in contraction. If it doesn’t work out exactly the way we’ve envisaged it we get upset, which puts us into a negative emotional state. From this place it’s hard to think creatively. It’s hard to explore other options. It’s hard to see that unexpected opportunity that’s actually the magic opportunity because we’re so focused on one specific solution.
My own coach, Victoria Song, lives her life by the mantra: this or something even better, meaning that she’s always open to something else (even better) being the solution or direction. This allows for a lightness around goals and dreams that helps keep you in an open and positive emotional place that is ideal for creating big things. It’s a phrase I tell myself regularly and is why Caroline’s approach of holding everything a little bit looser is so important.
Caroline’s New York
EAT: I love baked goods, and am forever in search of the best croissant in New York City. L’apartment 4F is currently my number one, and their conveniently located new location is certainly helping their case.
DRINK: a cappuccino from Yanni’s. My husband grabs this for me every morning as he walks our dog. I like the act of kindness as much as the drink itself - a perfect start to a busy day.
RESET: getting outside and moving my body. I said it on the podcast, but I can say it again. I walk the west side highway a lot, and I never regret it.
FUN: we love an at home dance party. Our house runs on Taylor Swift - go figure! But joking aside, we love music whether it be a night out, a concert or an at home dance party, music is always on.
SHOP: lately I’ve been going to the specialty food shops in Chelsea Market. I love the care the owners take in their good. My 3 and 4 year old love to come with me, and to explore each shop. I’d say our cheese, bread and meat game have been elevated immensely by this new routine.
Shop Tuck Shop. /// Follow Tuck Shop.
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