How I Switched Careers to Pursue Writing Professionally

If you’ve thought about switching careers, you’ve undoubtedly encountered this classic dilemma:

Pursue dream and be broke vs.  Pay bills and stay in mediocre job

It’s a pretty common dilemma for writers, artists, and creators. You want to feel fulfilled in your career, but financial stability is also nice – and necessary. So should you give up your dream to afford a roof over your head or live like a starving artist so you can feel fulfilled? Either way, it feels like you have to give something up. 

As tempting as it may be to storm into your boss’s office and yell, “I’M OUT, CHAD!” you don’t have to make a drastic move. If you’re working full-time and want to make the switch, you don’t have to quit your job immediately. It may work for some people to take the leap without a safety net, but having that net in place will save you from setbacks. When you switch careers without a plan, you make yourself more vulnerable to failure.

Jumping without a parachute works for some people, but there are so many things that can go wrong. If you’re anything like me, these things can cause you to stress out and give up on your dream altogether.

Balancing Support Work With Dream Work

When I was employed as a technical writer, I was happy. I loved my coworkers. We had free breakfast every Friday. I made pretty good money, and I was grateful.

Still, I knew I wanted to pursue a different kind of writing career. My writing goals have changed over the years  — I wanted to be a journalist, then a novelist, then a screenwriter, then an essayist  — but regardless of the medium, it was always my goal to write creatively for a living. Despite the fact that I liked my job, I knew I had to leave it.

You don’t have to quit your job, either. I’ve met plenty of people who have a “support career” and a more creative career on the side. They do what they love and they pay the bills. Eventually, switching careers may be an option, but in the meantime, they’re happy doing both.

However, if you do want to quit your job, consider strategizing an exit plan. It comes down to a few steps:

  1. Look for side work while you’re employed in your support career
  2. Save up money to support yourself when you DO decide to quit
  3. Set an end date in which you would like to leave and launch your switch

Here’s exactly how I followed each of those three steps to craft my own career switch.

Line Up Gigs While You’re Still Employed

The moment I got my first technical job out of college, I started looking for freelance writing work. I was pretty aimless at the time, and I didn’t even think switching careers was in my future. All I knew was I wanted to write, so I started writing on the side for extra money. While I was employed in a technical job for three years, I always had a side gig or two:

  • Writing press releases for local small businesses
  • Writing gallery reviews for a local art magazine
  • Writing and editing web copy for local businesses

None of these gigs paid particularly well, but they served a purpose in helping me learn how to become a freelance writer. They let me build my skills and experience so that when I did end up switching careers, I could command more money. It was also easier to find work with some experience under my belt. Finally, these jobs gave me a taste of what it was like to work with deadlines and make editors happy.

Build a Career Switch Fund (and Schedule)

Two and a half years after graduating from college and working as a technical writer, I knew my exit was coming.

I was lucky enough to have a job that paid pretty well, but I was spending that money on expensive clothes and overpriced candles for my apartment. Meanwhile, I had an itch to do something entirely different with my life, so I had a realization: Why am I not using the money to scratch that itch?

I started saving. At first, my savings goal was vague. I was just saving as much as I had left over every month, trying to be more conscious about my spending. It worked okay, but then I actually made that goal SMART (specific, measurable, assignable, realistic, time-based):

  • Specific: Save 6-8 months’ worth of living expenses
  • Measurable: I would measure my progress in a savings account
  • Assignable: The savings would come from my paycheck and any side gigs
  • Realistic: I had to save $1,000 a month. Realistically, it would take me about a year, probably more.
  • Time-based: I would try to reach my goal in one year and leave my job.

This helped me come up with a schedule for leaving. Making the goal SMART, even if I wasn’t familiar with the concept at the time, helped me come up with a realistic plan for leaving my job and doing something else. By specifying how much I would need, it was easy to figure out how much I would need to save every month and how long it would take me to get there.

Looking back, I probably should’ve saved more, but it worked out. I figured if worse came to worse and I couldn’t find work within three months, I would get a support job, even if it was working at the grocery store, in order to keep my savings intact.

Job Crafting: Make Your Current Job More Meaningful

With an exit plan in place, it’s easy to start shirking the responsibilities at your current job. You stop taking it so seriously. Maybe you even start resenting it.

This is not a good idea. For one, you’re still getting paid to carry out specific responsibilities, so putting in an effort is just the right thing to do. But by ignoring your work, you also miss out on opportunities to use your current job to support your future one.

During the year I was saving for my career switch, it was easy for me to look at my job and think “this isn’t at all what I want to do with my life.” Instead, I approached it this way: I’m building the basic writing, editing, and communication skills (and financial cushion) I’ll need to launch a more creative career. It completely changed how I approached my work and how I benefited from it.

Yale researcher Amy Wrzesniewski talks about this concept in the context of “job crafting.” In this article over at The Cut, she told me,

“One of the things I find exciting about job crafting is it’s not just about getting people to think about their work differently. It’s behavioral. Changing the way you think about a job cognitively changes the way you approach your tasks, then changes how those tasks would then unfold.”

In other words, you can literally change your job experience just by thinking about it differently and therefore approaching it differently. It’s a fascinating concept and I recommend reading the entire article, but job crafting basically comes down to three steps:

Step One: Understanding what your employer wants

Step Two: Understanding what you want

Step Three: Finding the intersection between both

For example, when I was “stuck” in my first technical writing job and I wanted to be a journalist, I found a way to sneak some journalism skills into my current job. Since I had to write technical manuals on how to put together different gas sampling tools, I interviewed everyone I could about this  — the manufacturers, the engineers, the salespeople. I got really comfortable with asking questions and truly understanding the concept. It was boring work, but it was the perfect job to help me build my writing and communicating skills.

There’s this subtle idea that if you’re not struggling or risking everything, you’re not adequately pursuing your passion. When it comes to achieving your goals, though, I’ve found that kind of “all-or-nothing” emotional thinking doesn’t get you very far.

The work involved with reaching your goals is less about inspiration and risk and more about building habits and scheduling time to work. In other words, the biggest thing separating your dreams from reality might be some simple planning.

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