Have you ever woken up in the middle of the night or first thing in the morning with your mind racing about work?
Maybe you start replaying decisions you’ve made, wondering whether you handled something poorly, whether you should have taken a different opportunity, or whether you chose the wrong career altogether.
The questions can be difficult to shake:
- Did I screw this up?
- Did I make the wrong choice?
- Is this really what I want to keep doing for the rest of my life?
I’ve had conversations with dozens (maybe hundreds) of people who have found themselves in this position, particularly when they’ve spent years building a career that looks successful from the outside but no longer feels right on the inside.
When that happens, it’s easy to look backward and question the decisions that brought you here. But before you conclude that you chose the wrong career, I want to offer you a different way to look at your professional journey.
Your Career May Look Different Than You Expected
My own career is a good example of how much things can change over time. I started in mechanical engineering and software after earning a mechanical engineering degree.
Today, my work looks quite different. I spend my time coaching, writing, speaking, teaching, creating content, working as an executive recruiter, and helping people navigate intentional career transitions.
If you had shown that job description to the 24-year-old version of me, I’m not sure he would have believed it.
Does that mean I chose the wrong career when I studied mechanical engineering or started working in software? I certainly don’t think so.
I still love engineering, and I remain closely connected to the engineering community. My experience in that field has shaped the way I think, the people I know, and the work I do today. Engineering taught me how to solve problems, think in systems, understand organizations, and appreciate the challenges engineers and leaders face. It gave me experiences that continue to inform my coaching, writing, and work with technical professionals.
I couldn’t do what I’m doing today without that chapter of my life.
Looking back, I can see how my earlier experiences contributed to the person I’ve become, even though my current career looks very different from what I might have imagined when I started. That’s an important perspective to remember when you begin questioning your own professional choices.
Stop Treating Your Career Like a Multiple-Choice Test
Sometimes we evaluate our careers as though we were taking a multiple-choice exam. We imagine that there was one correct answer, and if we selected the wrong option, we somehow failed.
Maybe you chose mechanical engineering when you should have studied computer science. Maybe you accepted a job at a large corporation when you would have been happier at a startup. Perhaps you pursued management and discovered that you preferred technical work, or you stayed in the same industry long enough to realize that your interests had changed.
When you look back, you may be able to imagine a different path that seems more appealing. But you’re evaluating that earlier decision with information you didn’t have at the time.
When you make a career decision, you’re working with the knowledge, identity, needs, and opportunities available to you in that moment. You have a particular set of skills, a certain understanding of yourself, and a specific set of circumstances. You make the best decision you can based on what you know.
Then life happens.
Your priorities change. You develop new strengths. You discover interests you didn’t know you had. Your family circumstances evolve, your responsibilities shift, and you gain experiences that change how you see the world. A role that once felt like an excellent fit may no longer provide what you need today.
That just means you’ve continued to grow and learn, and your career needs may have shifted along with you.
Look Back to Learn, Not to Punish Yourself
When you’re unhappy with your current career situation, it’s natural to revisit the decisions that brought you there. Reflection can be valuable, particularly when it helps you recognize patterns, understand your preferences, or make better decisions in the future. The problem comes when reflection turns into repeatedly criticizing yourself for choices you can no longer change.
Instead of asking, “Did I choose the wrong career?” try asking questions that help you understand what your experience has given you and what you want to do with it.
For example:
- What has this career given me so far? Consider the skills you’ve developed, the relationships you’ve built, the opportunities you’ve had, and the experiences that have shaped you.
- What have I learned about myself? You may have discovered the kinds of problems you enjoy solving, the environments where you thrive, or the responsibilities you would prefer to avoid.
- Who have I become? Think about the confidence, judgment, technical abilities, leadership skills, and perspective you’ve developed through your work.
- What do I now know I don’t want to continue doing? Even difficult experiences can help you become clearer about your values, priorities, and professional needs.
- What am I preparing for next? Consider how you can use your existing experience as a foundation for the next stage of your career.
These questions help you extract useful lessons from your past while giving you room to make different choices going forward.
You don’t need to convince yourself that every experience was wonderful or that every decision was perfect. Some choices may genuinely have been mistakes, and some experiences may have cost you more than you expected. You can acknowledge those realities while still recognizing what you learned and how you’ve grown.
Your past deserves an honest assessment, but it doesn’t deserve to become a reason to keep punishing yourself.
Don’t Let Your Past Become a Reason to Stay Stuck
Please don’t get stuck in the sunk cost fallacy.
You may feel that because you’ve invested 10+ years in a particular career, you need to keep going. You’ve spent so much time developing expertise, building a reputation, and establishing yourself that changing direction feels like throwing all that effort away.
That investment can make it difficult to consider other possibilities, especially when you’ve reached a level of success that others admire. You might think, “I’ve worked so hard to get here. How can I walk away now?”
But the time you’ve already invested cannot be recovered, regardless of what you decide next. The more useful question is whether continuing on your current path makes sense given what you know today.
You don’t have to stay in a career simply to justify the years you’ve already spent there. Equally, you don’t need to abandon a career just because you’ve started questioning it. The goal is to make an intentional decision based on where you are now and where you want to go.
Use Your Experience to Build What Comes Next
If you’ve reached a point where you know something needs to change, give yourself permission to explore what that change might look like.
Start by identifying what feels misaligned. Perhaps you want more meaningful work, greater flexibility, new technical challenges, a different leadership opportunity, or a career that better accommodates your family and personal priorities. Get specific about what you want more of and what you want less of.
Then begin exploring your options. Talk to people who are doing work that interests you. Look for ways to use your strengths in a different context. Consider whether a new project, role, team, or organization could give you what you’re missing. If you’re contemplating a larger career pivot, experiment with possibilities before making a major commitment.
You don’t need to have your entire future mapped out before you take action. You need enough clarity to identify a reasonable next step, learn from it, and decide what to do after that.
Looking back can help you understand how you arrived at this point, but looking forward is what opens up new possibilities. Your past career doesn’t have to define your future. It can provide the experience and perspective you need to build it.
Your Next Chapter Is Still Yours to Create
If you’re lying awake often wondering whether you chose the wrong career, I encourage you to pause before judging the person who made those earlier decisions. That person was working with the information and circumstances available at the time. Since then, you’ve learned, grown, and changed.
Take what your experiences have taught you, including the difficult lessons, and use that knowledge to make more intentional decisions about what comes next. You can appreciate the opportunities your career has provided while acknowledging that you may be ready for something different.
You don’t have to justify staying where you are, and you don’t have to make a dramatic change simply to prove that you’re moving forward. You can take time to understand what matters to you now and choose a direction that better reflects the person you’ve become.
If you’re asking yourself, “Did I make the wrong decision? I don’t know what to do next, but I know something needs to change,” this is exactly the kind of work I help people navigate through my Engineering Career Accelerator program. Together, we can explore your options, gain clarity about your direction, and develop a practical approach to making a career transition.
Please don’t try to figure everything out alone. Reach out to connect with me on LinkedIn or by email at jeff@jeff-perry.com, and take a look at the free resources available at https://jeff-perry.com/resources/.
Your career has already taught you a great deal.Use those lessons to move toward a future you’re genuinely excited to build.
I can help!
Watch more in the video below:
