Career Regrets

Do you have any career regrets? I do.

I’m 45 years old. I’ve had a weird career. It started out pretty “normal” (for the olden days), but with my first real layoff in 2006, things have been very much outside of normal.

Here I am, recently laid off from what was supposed to be my dream job at a dream company, and I am kind of unhireable.  In interviews I’m missing out one one or two things (like a certification, or a very specific experience). In at least one interview I’ve had a young VP of product super worried that I had a side gig, and he thought I wouldn’t do the job because I’d focus on my side gig.

I did what “they” told me to do, years ago, and got a technical degree. And I got an MBA. And somehow, someone said that speaking a foreign language would be really valuable in my career (it hasn’t been, although I do love speaking and listening to Spanish, and the whole new world it has opened up for me).

That old advice almost means nothing in today’s world.

I regret, since leaving school, not doing more for my career management.

The irony is that my best in-person presentation is titled Career Management 2.0.

In that presentation, I focus on networking (relationships) and personal branding. I squeezed this into 45 minutes once, and one time I went for 3 hours (and people asked for more… it was really cool).

And here I am, confessing my regrets.

I wish that I would have gotten my PMP certification to quantify my project management skills.

I wish that I would have developed more institutional product management skills. The lack of this has been a problem in interviews… even though I’ve done product management for 20+ years, the interviewers have made it clear they want someone who has institutional (not necessarily practical) experience.

I wish that I would have taken classes in UX. Not graphics, not design, but UX.  I think this is one of the most important fields for every organization.

Those are the three things I should have dove deeper into over the last 13 years. I would have been able to add considerable value to my JibberJobber users, and probably would have had a six figure job years ago.

After working at Bamboo, I wish I would have also dug deeper into marketing. I worked with some crazy smart marketing professionals there, and learned a lot from them. Oh, how I wish I would have been better at that.

I mean, I wasn’t just sitting around. I wrote 3 books (one has 4 editions, each were complete rewrites). I just turned in my 32 Pluralsight course (doing one course is a huge accomplishment). I became a professional speaker (it’s like a public speaker, but you get paid to do it :p), and published LinkedIn how-to DVDs. I was self-taught in many of these things, and I help people know how to do these things for themselves.

So yeah, I have regrets. But I also have so many hours in the day, and I can’t turn back time. I’m not losing sleep over it. BUT, if I ever get a chance to mentor anyone, or give advice or tips, I will definitely encourage them to continue their education… work on professional certifications and other learnings that are quantifiable.

That’s my regret, and that’s what I’m doing about it.

Now, what are you regretting with regards to your career, and what are you going to do about it?


2 thoughts on “Career Regrets”

  1. Very good advice.

    I try not to have regrets. One thing I’ve learned is that you there are things you learn even on the wrong path, that you might not have learned had you done the thing you have regrets about.

    That doesn’t mean that every previous decision was the best, but I really agree with helping others learn some of the pitfalls more easily than going through them directly.

    I do wish I had understood the multiple income streams — practically — earlier. But that is what I am teaching my children.

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