Sometimes a mistake can turn into a positive.

Maybe you accidentally copy an email to someone that contains complaints about that person. That's a potentially ugly situation that could end a relationship, or it could lead to an apology followed by an open conversation.

Sometimes a mistake in your career can be turned into a positive. That's not always immediately obvious, but over time, lessons can be learned, and what was once painful can become if not illuminating, at least valuable when looking back.

A man stands at a fork in the road.

Making a career mistake can sometimes become a positive. Image source: Getty Images.

Taking a job I didn't want

Maurie Backman: Back when I first started freelancing, I was, admittedly, pretty desperate for work. Though I knew it would take some time to develop a client base, for each day that went by when I didn't earn a dime, I grew increasingly nervous. It was that desperation that prompted me to take a job I knew I shouldn't accept.

I found the job through a freelancers' board online, and the ask was simple enough -- create a series of blog posts for a start-up marketing firm. The problem, however, was that the pay was laughable, and as part of the arrangement, I had to agree to unlimited edits before I could be paid for a particular submission.

I had a really bad feeling about the job, but I went in with a positive attitude -- only to realize immediately that I'd made a huge mistake. My first 10 posts -- yes, 10, because they wanted them as a batch -- were ripped to shreds, even though I'd followed directions to a tee. I reworked those posts, resubmitted, and held my breath, and sure enough, they were rejected again. I finally had to walk away, unpaid, after countless hours of back and forth with virtually no progress.

But here's the silver lining in all of this: I learned very quickly what sort of jobs not to accept as a freelancer. And from that point on, I only took jobs that paid me a fair wage and came with reasonable demands. It's easy to sell yourself short when you're desperate for cash, but there comes a point when your time and sanity are worth more than a few extra bucks.

Not having a plan

Selena Maranjian: I look back on my college days now and marvel. Like many kids, I didn't really know what I wanted to do or be after college -- even as I approached graduation. Unlike many kids, though, I didn't think things through carefully, making a list of possibilities and their pros and cons. Instead, I just figured I'd go to grad school because I couldn't think of anything else.

For a variety of reasons, I abandoned that Ph.D. program after one year and embarked on a mishmash of career moves -- getting a different postgrad degree, teaching high school, getting an MBA, and eventually landing at The Motley Fool. I see my not having had a plan as a mistake, as it would have been better to have thought more about career possibilities while I was still in school. I might have landed on a job that was a great fit for me.

Instead, I ended up on a zigzaggy path to where I am now. It all ended well, though, because I still ended up in a great place, doing the kind of work I enjoy and earning enough to keep a roof over my head.

I would recommend that others do more thinking, exploring, and planning regarding their careers; just having lots of informational interviews with people in different fields can make a big difference, especially if you ask them what their days are like, what skills they use, what they like and don't like about their jobs, etc. Still, accidental career paths can work out well, too.

Being too ambitious

Daniel Kline: In my early-career days I had a furious desire to be in charge. That was partly because I never liked being told what to do, and partly because I wanted the status and esteem of being the boss.

I had not learned that paying your dues and gaining experience matter at least as much as skill, ambition, and hard work. I had also not learned that being the boss (at least the way I do it) can eat you alive, as the problems of everyone who works for you become yours.

That mode of operating -- or character flaw -- followed me to various professional stops along the way. Sometimes I got the job, sometimes I didn't, but in all cases I would have performed better had I focused more on the moment and less on taking over. And when I did get the job of boss, on a number of occasions, I built up ulcers and lost sleep due to the stress of sitting at the top of the pyramid.

Now, at 43, I've run newspapers, websites, and a variety of businesses. I could probably land a fancy title and a job where I got to be the boss if I wanted them. I don't.

It's a happier life to work with people you respect who value your opinion and input than it is to be in charge. I'm not opposed to running things, and I certainly take leadership positions on projects when asked, but it's no longer a motivation. Had I figured that out sooner, I would have spared myself a lot of grief, and perhaps I would have had a smoother path to getting where I have happily ended up.

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