My three biggest career mistakes

Most of us don’t get too far in our careers before making some sort of mistake. I’m sharing mine here in case it helps someone avoid the same mistakes I made.

Taking a dream job

I used to fervently believe in dream jobs. Not only that, but I focused significant energy on finding my dream job. This belief and hefty dose of optimism led me to take a job that for many reasons was an unmitigated disaster. By believing that a dream job existed, I ignored potential problems. I swept those red flags right under the career rug. By refusing to look at the potential trade-offs or downsides of the opportunity, I was shaken to the core when it turned out not to be so great.

My job went from dream to nightmare very quickly. In fact, it was so bad that I cried nearly every day for the entire six months I was at that job. I’m not actually exaggerating. I was utterly embarrassed to announce that I was leaving just a few months after declaring it my dream job.

Embarrassment aside, I’m kinda glad it happened. I learned an essential lesson.

No job is a dream job. Every professional situation has some downsides. Maybe it’s the right role but your boss isn’t an ideal fit. Or perhaps the role doesn’t turn out to be exactly as advertised so instead of doing the work you love the most, your day-to-day entails something that’s much more uncomfortable. Now I know that sometimes there might even be good reasons to stay at a job you hate.

Lesson learned: Be realistic

When you look at new opportunity realistically without the rose colored lenses of a dream job, you can more accurately assess the potential trade-offs. So if a part of the job goes south, you’re less likely to be surprised and more likely to be able to find your footing faster. As a recovering workaholic, I've discovered that a more realistic attitude about my career translates into having other hobbies and interests outside my work. If I do find myself less fulfilled in my professional life, it doesn't crush me as I'm happier with other aspects of my life.

Confusing my skills with what I enjoy doing

I got my start in tech managing million dollar projects for an interactive agency. It was a company full of smart, creative people — some of the best I’d ever worked with. Along the way, I was given challenging projects, the ones that were complex or needed rescuing. Managing logistics and processes was like second nature for me; I found it all easy. Given the startup nature of our company, we lacked many basic processes, so I created them to help me in managing my projects and teams.

I got so good at project management that I was promoted to head the department. The work weighed on me and I wasn’t super happy but I was too busy clocking 60-70 hour weeks to do much about it. Then the recession hit; the agency went under and we all lost our jobs. As I hit the unemployment office, I pondered what to do next. While heading the department I’d discovered how much I loved supporting others in their careers. So as the economy foundered, I transitioned my career to become a certified career and executive coach. I didn’t make much money those first years but it was incredibly fulfilling. 

Eventually I had found my way onto the board of an industry organization in a role which mostly consisted of project management. I discovered that even though I was good at it, I hated project management. Finally I understood why I didn’t like my project management job, despite loving my colleagues. I was good at managing the work of others, keeping projects on track and figuring out how to make a deadline. Still, I hated what I was doing.  After that I vowed never to do work I didn’t enjoy, no matter how good I was at it.

Lesson learned: Being good at something isn’t the same as enjoying it

Just because you’re good at something doesn’t mean you have to do it for a living. Learning to make the distinction between things I was good at and things I also liked to do was a career changer for me. You might be good at something you dislike doing like troubleshooting hairy technical problems or tracking down trouble-some bugs. Just because you have a skill, doesn’t mean you have to use it. Don’t take on roles that require you to do work that exhausts rather than uplifts or is interesting to you. Never allow someone else to define your professional path for you. If you find yourself in a role that requires this skill for a large part of your tasks, it might be time to leave.

Not knowing my worth

It was the height of the 2008 recession. I’d been laid off twice — in a year. After six months of job searching, I needed money, and fast. I was finally making progress. I had two really good opportunities. I took the first offer without negotiating or finding out if the other company would counter offer. I actually accepted the job right there on the phone, when the CEO called to offere it to me. I didn’t negotiate a thing. The problem? The salary he offered was 30% less than my last job. Yes, it was the recession, yes I was desperate. It was still a mistake.

After I got off the phone I knew I'd done the wrong thing. Not only was I  underpaid, the salary meant I would have a tough time paying my bills -- and the job was high pressure. My self-esteem took a dive after that and I stopped trusting myself.

Not knowing your worth often shows up in negotiating a salary — not doing it all or not doing it enough. But the implications of not understanding your value has farther reaching consequences than salary negotiations.

Not valuing yourself might make you reluctant to raise your hand to take on challenges projects, eventually stagnating your growth. When you work for yourself not knowing it can mean not charging enough or putting up with bad clients far too long.  You might not monetize that side project, even though it provides a ton of value to others. For me, not knowing my worth also meant wasting too much time on one-sided relationships or trying to help people who didn’t want to help themselves. 

When we undervalue ourselves, it can haunt us, burrowing deep inside us, affecting future decisions about our careers.

 Lesson learned: 

This career mistake is really about confidence. When you don’t know your worth, you don’t trust yourself and are much less likely to advocate for yourself. Even though this career mistake smarted for a long time, it was a turning point. I learned to see my capabilities and my value in a more realistic manner. After that I started listening to and advocating for myself. I stopped making career decisions that made me feel bad.

I’m not saying that if we advocate for ourselves that we’ll get our fair share. There are still plenty of factors at play that we can’t control. What I’ve learned is that when I know my worth, I focus on situations and people who bring me up, rather than down. When I know my worth, it’s far easier for me to ask for what I want rather than eagerly taking whatever is offered to me. When I know my worth, I have less stress and more career fulfillment.

I’ve also learned never to take an offer on the spot. I now have a 24-hour rule when for sizable career decisions. Having time to sleep on it helps me slow down and make sure I’m happy with the situation or if I need to change the terms.

P.S. You might want to read this thread about biggest career mistakes. If you share your own, please tag me so I can read it.