If Willy Wonka Was A Former Engineer

There’s this whisper so many of us hear when we’re in transition. 

You’ve never done this. How are you going to do this? Are you sure this is going to work? Maybe this was a mistake.

New job? Starting over. 

New relationship? Starting over. 

New dream? Definitely starting over.

But the truth is, you’re never starting from scratch. You’re starting from experience. Every misstep, success, and late-night “what now?” is data you get to use this time around. You’re not new; the experience is.

And maybe it’s not about the start at all, it’s about the pursuit. The pursuit of meaning, alignment, and becoming who we already are.

That came through so clearly in this week’s conversation on Wait — What Do You Do Again? with Brian Krichbaum, co-owner of Gilbert Chocolates, a 125-year-old family company in Michigan that he and his wife, Sally, now run together. Their story isn’t about explosive growth or a viral moment that took off — it’s about what happens when you take what you’ve learned and build smarter the second (or third, or fourth) time around.

And look, being the owner of a chocolate company sounds amazing. But Brian will be the first to tell you it’s not all Willy Wonka and cocoa dust. When he and Sally took over the business, the longtime owner saw what sustainability would take, pulled a Danny Glover and said, “I’m too old for this,” selling them a beloved but cramped 800-square-foot cottage that served as both factory and store.

Instead of taking out loans or chasing instant expansion, they focused on steady progress; fixing what was broken, modernizing equipment, and keeping quality at the heart of every decision.

Theirs is a story of real-life growth: the exciting, hard, unsexy kind. Built on optimism, discipline, and a deep desire to succeed, they’re growing something that lasts.

A Few of My Takeaways:

1. Start with what you have — grow smart. Brian and Sally improved what they had and prioritized quality. By avoiding large loans for quick expansion, they’ve been able to focus on sustainable growth and weather life’s curveballs.

2. Legacy is a strength, not a limitation. Instead of feeling trapped by the company’s long history, Brian and Sally treated it as a foundation. They honored tradition and evolved the business — adding vegan options, embracing e-commerce, and keeping the heart of the brand intact.

3. Partnership takes re-learning. Working with your spouse, family member, or friend means unlearning old dynamics and creating new ones. Sally and Brian learned to work with each other, not at each other. (Spoiler: they’re still married.)

4. Optimism needs structure. Dreaming big matters — but it has to be grounded in discipline. Brian’s optimism was backed by planning, process, and a willingness to adapt when things went sideways (like snowstorms disrupting shipments right before Christmas).

All of it circles back to that bigger idea that growth is about doing it better and creatively because you know more now.

If you’re open to it…

Think about something in your life that feels like a restart.

What lessons from the last round could you bring forward this time?

How can you apply what you’ve already learned (especially the hard parts)?

xoxo,

Meghan