Over the course of a long career, nearly everyone has regrets. You wonder about the path not taken and where it may have led.

In some cases, even as we pass on things or choose to not go after them, we know we're being risk-averse in a way that could hurt our careers. It's easy to do that, because taking risks means things may not work out and you might fail.

In hindsight, though, sometimes it's easy to see where not taking a risk turned out to be a mistake. Here, three Motley Fool investors look back at the risks they wish they had taken.

An illustration of a woman standing at a fork in the road.

It's not always easy to know which risks are worth taking. Image source: Getty Images.

Writing a book

Maurie Backman: Though I started my career in finance, writing has always been my passion, and so I'm happy to say that I'm finally doing what I love. But if there's one other thing I'd really like to do, it's write a novel.

Now technically, I've written one already, but it's sitting on a flash drive in my office in fairly raw form, and I'm not even sure I want to publish it. But in general, part of me wishes I would've taken time off from my paying gigs years ago to hammer out a novel I'd feel good about submitting to a publisher.

The only reason I didn't when I was younger boiled down to money, and my fear of not having an income. And now that I'm older, and have a mortgage, car payment, and host of financial responsibilities, it's not something I see myself doing anytime soon.

That said, I'm not giving up on that particular part of my dream. Perhaps I'll reach a point where my savings are stronger and my expenses are lower, and I feel more comfortable taking on the risk of sinking months into a project that may not yield me so much as a penny.

But for now, it's just not in the cards, and I'm also OK with that. I still have that initial novel, rough draft and all, tucked away for safekeeping, and who knows -- I just might rework it and publish it one day.

Making the jump sooner

Jason Hall: Before I started writing full-time for The Motley Fool, I had a pretty successful career. I was well established in my industry and well known among my customers and competitors, and I made a solid living. I also had the usual corporate benefits, including a 401(k), healthcare, and paid time off.

But I didn't have one of the most important things that a career can give: a sense of purpose. 

I spent a couple of years freelancing part-time for the Fool while still working my day job before making the jump, and I knew that I was helping people invest better. I knew that I wanted to do this full-time, that regular people -- people like me -- struggled to find reliable insight to make better investing decisions. And I knew The Motley Fool gave me a platform to do just that. 

But I was afraid to make the jump -- afraid to walk away from the predictability of working for a big company with all the benefits and salary that come along with it. As a contractor for The Motley Fool, I'm more like a small-business owner than an employee, and it can be pretty scary walking away from the comfort of what you have to pursue even something that you have a passion for. 

While it's certainly worked out great, I wish I'd taken the leap sooner. I spent a couple of years not doing what I wanted to do, letting my fears about the risks of starting something new keep me from doing something I wanted to do far more. It was a risk leaving a great job for the uncertainty of being a full-time writer. But it's one that, in hindsight, I should have taken sooner. 

Not being willing to move

Daniel B. Kline: In the early days of my work life, I had dreams of being a radio talk-show host. That's an unbelievably challenging space to get established in where even talented people lose their jobs.

To have any chance of entering that space, however, a younger person needs to to be willing to move. In my 20s I lived in New York, which is a top-tier market. Had I been willing to move somewhere much less populated, I probably could have landed on-air work.

That would have meant committing to at least a few years, maybe longer, where I would move quite often. I would have had to establish myself in small markets, then move to a bigger one, repeating that process until I was successful somewhere I wanted to be, or until I gave up the dream.

Instead, I didn't want to leave my comfort zone, my friends, and whatever other things seemed essential in my 20s. Now, at 44, I can't pack up to move to Iowa to get barely paid to host a talk show. I am lucky that through my work at The Motley Fool I do get to guest on radio shows and appear on podcasts. I do, however, wish that when I was younger I had taken the risk to find out if a job I still think I'd have been pretty good at would have been everything I dreamed it would be.

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