A man stands in front of a blackboard full of question marks.

Not every choice in your career will be an easy one. Image source: Getty Images.

In my 23-year working life, I've held 16 distinct jobs. That count admittedly includes some positions that overlapped, but it's my best guess at a total for a career that has taken me from newsrooms to a toy store and from Playboy to The Boston Globe.

I've run a factory, done public relations for a non-profit, and worked at a now-defunct internet pioneer that held an initial public offering. I served as executive director for a rock band camp for kids, curated content for Microsoft's news and finance apps, and most recently have spent nearly four years writing for The Motley Fool.

It's a career that has not always made sense, but one that has taught me a lot of lessons along the way. By stumbling around from job to job for over two decades I've learned a lot of things have helped me, which can also help you. Not every lesson here ties directly to a specific job, but each one has been learned over a long, twisty path to my current employment bliss.

Two men shake hands.

Sometimes change can be a good thing. Image source: Getty Images.

Don't fear change

At various points in my professional life I've left a job because of pending changes in management or in company strategy. That's OK if you know the new person in charge is a bad choice (or at least a bad choice for you) or that the changed direction is a mistake.

For me, however, that has not always been the case. I've generally been afraid of change because, well, it's uncomfortable. It's not always the right choice, though. At one job, a boss I liked was pushed out and replaced by a total stranger. The new boss turned out to be a good match for me, one who supported my career then and has ever since. Had I followed my instinct to flee before major change, I never would have learned that.

A man hands over multipe hundred dollar bills.

Money is important, but it's not everything. Image source: Getty Images.

Experience can trump money

Obviously everyone needs to make a certain amount of money. If, however, you find yourself choosing between two positions, don't automatically take the one that pays more.

Weigh what you will learn, what you will do, and the experiences each position brings. If the lower-paying job has an edge in those areas and will leave you better off in the long run, consider taking it.

A plane is seen in the foam on a cup of coffee sitting next travel documents.

Take advantage of opportunities to move or see other parts of the country or even the world. Image source: Getty Images.

Travel while you can

Right out of college I had the opportunity to move from New York to Philadelphia for a two-year job program. I also had the opportunity to try out as one of the people driving the Oscar Mayer hotdog around the country. I passed on both because I was afraid to leave the comfort of being near my friends.

In reality, as you get older, whether you move or not, other people do. Take work travel opportunities while you can because once you have a spouse, a mortgage, and a child (as I do now) moving for work becomes a much harder proposition.

A man gets ready to throw a paper airplane from his desk in an office

Don't take a job you won't find stimulating. Image source: Getty Images.

Never settle

At various points in my career I've taken jobs that I knew wouldn't work out in the long-term. Maybe I convinced myself that I could make a go of it, or maybe I just wanted to stop looking for something better.

In reality, while taking a less-than-ideal job just to make ends meet may feel good, it almost never works out. Unless you are unemployed and need the money, it's always best to keep searching until you find what you're looking for.

A woman raises her arms in triumph.

Believe in yourself or nobody else will. Image source: Getty Images.

Believe in yourself

Before I became a financial journalist, I kept applying for jobs in the business/finance space. I was mostly met by people telling me I had no experience in that space.

That was true, I had no direct experience -- but I was convinced I had enough indirect experience to do the job. I had run a retail store and a factory where I bought commodities. That plus plenty of journalism experience made up, in my opinion, for the fact that I had never had a full-time job covering business/finance.

While that attitude may have seemed a bit arrogant, I had it not only because of my faith in myself, but because I had seen what others could do. At countless jobs I watched co-workers perform tasks they weren't qualified for or find a way to get the job done well, even when their resumes suggested they wouldn't be able to.

Sometimes it takes a person willing to give you a chance (in my case my first boss at Microsoft, who gave me my start as a business journalist). In other cases it might take a battlefield promotion where you fill a role because nobody else is available. Whatever it takes, it will only happen if you believe in yourself and make it so.

An illustration of men holding onto an arrow poitning into the air

Take a long-term view and your career can go steadily upwards. Image source: Getty Images.

Play the long game

For my first few jobs, at a variety of magazines, newspapers, and websites, I came in, saw what was wrong, and immediately tried to take over in order to fix everything. I wasn't wrong about what needed to be done, but my approach was off.

The people who had been at those companies a long time did not take well to a new (and young) person coming in to tell them what they were doing wrong. That made it hard, even when I had the authority to make changes, to get things done.

In every case, I would have been better off playing a longer game. Make small changes, nudge the organization in the right direction, and save the big pivots until after you've won respect and support.

Perhaps a respected, grizzled veteran can come in and immediately take over and make huge changes. Most people aren't that person, however, so for most of us playing a longer game makes sense.

People network at an event

It's important to meet people in your field and keep up the contacts. Image source: Getty Images.

Who you know matters

I've seen people with no business being hired get a job because they knew the right person. Sometimes those people fail, but in other cases all they needed was a chance.

That taught me that it's better to be the person who gets a job through a connection (and then performs well) than to be on the outside looking in. Cultivate relationships and consider them a long-term asset as you navigate your career.

A student studies in a library.

Keep learning whether it's in school or elsewhere. Image source: Getty Images.

Keep learning

Many years ago, before I married my wife of 17 years, I decided to go to one of those broadcast schools they advertise on the radio. It was a good experience and I probably could have landed an entry-level on-air position in a small market, but I never pursued it, and for years the money spent seemed like a waste.

Years later I co-authored a book and did hundreds of interviews on the radio. Since then, I've appeared on podcasts and radio now.

You never know when learning something new will pay off. I've been in work situations where the fact the I spent years taking Spanish lessons has paid off, even though my skills are basic to say the least. If your office offers training or learning opportunities, take them -- even if the benefits are not immediately obvious.

Co-workers huddle around a computer.

Be a good teammate. Image source: Getty Images.

Be a good teammate

In my many career stops I've worked with hundreds, maybe thousands of people. I remember the truly bad ones, but mostly I remember the handful that went out of their way to work well with others -- the ones who sacrificed for the good of the team.

Those are the people I want to work with again, and the ones I've helped get jobs or served as a reference for.

A blindfolded man in a suit

Don't be blind to opportunity. Image source: Getty Images.

Have one eye open

If you love your job it's OK to be content and stop looking. If you don't, but aren't miserable, it's important to keep looking for a better situation. I've always been quick to move on, but I've seen colleagues get trapped in good enough jobs where they aren't exactly happy, but aren't exactly miserable.

Take the initiative to better your situation. Don't leave just to leave, but be open to the idea that something better is out there and that you deserve happiness. 

A man types on a laptop.

No matter how trivial the task, perform it well. Image source: Getty Images.

Do every job well

In my freelance days I took a number of jobs that were perhaps beneath my talent level. In two cases relationships I made doing fairly tedious work led to much better jobs down the line (in one case I got the job, in the other my relationship led to my wife getting hired).

In another case, much earlier in my career, I took a grunt job fact checking at a major magazine and did it OK, but not well. Perhaps that cost me a position down the line. It certainly cost me having anyone who worked there give me a recommendation.

A confused man looks at a blackboard full of equations.

It's OK to sometimes get an answer wrong or make a mistake. Image source: Getty Images.

It's OK to make mistakes

I've seen bad bosses yell at, or even fire, well-intentioned employees who made mistakes. When that happens everyone becomes cautious, and while mistakes may be eliminated, so too is innovation.

If you become a boss, embrace mistakes when they come from the the right place. As an employee, understand that striving for perfection may be a good goal, but it's not a realistic one.