This Might Change How You Make Big Decisions

I can be decisive when something feels like a full body yes (aka a “hell yeah!”). There are moments where the answer is immediate and clear. Leaving the practice of law wasn’t one of those moments.

I thought about it for years. It wasn’t because law was objectively bad. I worked with people I genuinely liked. I was well compensated. I had flexibility and autonomy. From the outside, it looked like a career that made sense to keep. But something inside me kept pulling in a different direction.

I felt misaligned with how I was spending my days. I was spending too much time in my inbox and in front of a computer. I wanted to feel like I was improving lives in a meaningful way. I wanted a deeper sense of purpose in my work.

When I discovered coaching, it resonated. It felt like the type of work I should've been doing all along. Even then, the decision to leave law didn’t suddenly become easy. Most of my attention went to what I’d be giving up. Security. Predictability. A steady income. A clear and established path. I’d built a career over many years, and walking away from it brought a lot of uncertainty.

At the same time, there was another question that I couldn’t ignore. What would I regret if I stayed?

I trusted that I could figure out how to start and grow something new, but I’d never done it before. That experience gap created self-doubt. The unknown was extremely uncomfortable. The decision held a mixed bag of emotions. Excitement. Fear. Doubt. Freedom. Loss. It wasn’t a “hell yes.” It was quieter than that. It was a recognition that if I didn’t try, I’d carry that regret.

In the end, the fear of regret outweighed the fear of uncertainty. So, I chose to leave law to start something new. What I’ve come to appreciate is that meaningful decisions often involve grief alongside opportunity. Sometimes the right path doesn't feel clear because we're not only moving toward something, we're letting something important go.

Every yes contains a no. It requires letting go of an infinite number of other opportunities. We don’t need to resolve the tension to make a wise decision. We only need to be willing to hold it.

A Reflection

This week, notice a decision that feels heavier than it “should.” When mixed feelings arise, pause before you interpret them as a problem. Can you allow a decision to be both right for you and still feel uncomfortable?

A Quote

“There is no greater agony than bearing an untold story inside you.”

— Maya Angelou

An Invitation

If you’re navigating a big decision that feels unclear, you don’t have to figure it out alone. Coaching offers a space to slow down, make sense of what you're experiencing, and move forward with self-trust, even when the path is not perfectly clear. If this resonates, reply to this email to book your complimentary discovery session. It’s a chance to explore what you’re navigating to see whether coaching could support you in making a decision that feels aligned and honest.