Why Making a Career Change Is Hard, Even When You Know What You Want

I had a plan for my ideal next career move sitting on a shelf. Before the pandemic, my coach, Christine, helped me create it: I wanted my own coaching and consulting business. But it felt too scary, a bit of a pipe dream. It was a someday plan.

The reason it stayed on the shelf was money. I’m financially conservative. For years, I balanced my need for meaningful work with financial security by working for someone else. I had a steady paycheck, a 401(k), stock options, great benefits, and a successful career doing work I loved. That security wasn’t just comfortable. It felt responsible. But parts of the work weren’t fulfilling, and by the time I was laid off, I was also burned out.

I’d changed direction before. I walked away from a career as a journalist when I was younger and the financial risks felt less pressing. Later, I made a career change quietly and successfully without blowing up my life. I’d found a way to move toward work that fit me better without giving up the security that mattered to me. This time, I couldn’t have both. Building something of my own meant no steady paycheck and no benefits.

When Security and Fulfillment Pull in Different Directions

I call this the messy middle of career change. I knew exactly what I wanted. I also knew what I was responsible for. A mortgage, my family, planning for retirement. Part of me said, “This is your chance.” Another part said, “Be sensible.” Both felt true and at odds.

I wish I could tell you I had a clear plan and confidently went after it. I didn’t. What I did have was a coach who helped me look at what was going on beneath the surface. I’d spent years doing work I was good at, work that gave me a professional identity and a steady income. Letting go of that was one thing. Giving myself permission to try something different without knowing how it would turn out was another.

Taking the Risk Without Ignoring Reality

Eventually, I decided to take the risk. I didn’t ignore the money question. I decided how much uncertainty I could live with. We downsized our finances, big time so I’d have a financial runway to get the business going.

And the first thing I did? I overengineered it. I set up a corporation, created processes for every eventuality, and tried to anticipate everything that could happen. Looking back, that was my need for security showing up in a new form. It was overkill.

I also realized I didn’t know how to market myself. Inside organizations, I’d never been responsible for generating my own business. Now I was, so I got help.

Three years later, things are still messy. I’ve made significant financial changes to make this business work, and I still worry about money. The tension didn’t go away when I made the decision. I just manage it differently now.

The Gap Between Knowing and Doing

I see this same tension with clients who are considering a career change. Sometimes people know exactly what they want, but there’s a gap between wanting a career or job change and being willing or able to make it happen. They may be worried about walking away from a career they’ve spent 20 years building, have financial responsibilities that make risk feel irresponsible, or feel uncomfortable being a beginner again.

For me, taking the risk didn’t mean I stopped caring about financial security. It meant I was willing to trade some certainty for the chance to build something that mattered to me. Even with all the messiness, uncertainty, and financial trade-offs, I wouldn’t change a thing.

What about you? Have you made a career decision that meant giving up some sense of security for something that mattered more? How did you weigh it, and looking back, would you make the same choice again?

If you're considering a career change but feel caught between what you want and what feels safe, you don't have to figure it out alone. Schedule a complimentary consultation, and let's talk about what's keeping you stuck and what moving forward could look like.