From Bartender to Freelance Writer: How to Prepare for A Career Change

I’ve been in the service industry for my entire adult life, except for one eleven month period when I got out. The phrase “got out” pertaining to someone leaving the hospitality industry is, I imagine, almost synonymous with a felon leaving prison.

The recidivism rate within the service industry is probably lower than most correctional facilities because, in prison, you can at least sit down every so often and punch someone in the face if they complain about the food. My first attempt at getting out of bartending sputtered and stalled, for several reasons.

I failed because I wasn’t prepared. I had money saved, but there was no budget. I lacked the emotional maturity so any rejection or hiccup sent my anxiety soaring. I would give up for the day and drink copious amounts of pinot grigio from a jug while watching HGTV and checking my dwindling bank account. I didn’t have a supportive partner or even close friends in the city I was living in. In hindsight, it’s no surprise I returned to bartending, serving (literally, ha HA) another seven years, or as they say on the inside, 84 months.

Now, it’s time to get out- for good. This will be tricky because I don’t have a job in another industry lined up. In fact, there will be no single job. I’m going from slinging drinks to freelance writing. Not a decision to be made lightly, I’ve been planning for this for a few months.

Make The Decision

I bartend in a corn maze

To be fair, I never liked my current job. Never mind the inconsistency, the low stipend for playing the role of bar manager (really, an inflated title they gave me to compensate for having to deal with a three compartment sink), or the exhausting physical aspect of it, what always bothered me was the low-grade sexism of the place. I’ve worked in places where the sexism was really blatant, which, frankly, would be welcome at this point.

Pointing out that a tank top for female employees reading, “Eat my pie,” is bullshit versus explaining that everytime I ask a question, turning away from me to face the nearest man to give the answer is much harder. Or wondering why male employees receive their supervisor pay on a different check than myself. If I wanted to be gaslit all the time, I would go back to my alcoholic ex.

Tell People/ Find a Support System

In order to make the decision real, i.e. not back out, I told people. So if I did back out, it would also be embarrassing on top of soul-sucking. Telling people what I want is hard for me so this was a good exercise. Plus, I could read their reactions to see if I was making a huge mistake.

To my surprise everyone’s responses were positive and told me to go for it. My partner offered to help as best as he could. Friends were excited to hear the news. I was not expecting an overwhelmingly positive response, but more on that later.

Create a Budget

Creating a budget is like cleaning out your closet. You find an old sweater you were missing (or money) along the way and at the end, even though maybe you tried on an old pair of pants and they’re way too tight (or it costs more to live than you thought), you’re at least facing the truth. Terrifying but cathartic.

To track what I’m earning and spending, I made an appointment with a financial consultant at Next Door, which is free and run by State Farm. How is this free? In return, they use your data to create entertaining commercials starring character actors and beloved quarterbacks so we buy more insurance products from them. Tit for tat, baby.

After a nice woman collected data from me (College? How did you get here? Rent?), she handed me a worksheet. The sheet listed expenses into categories: fixed, variable and non-monthly. Fixed is a set amount you spend every month like rent, variable would be bills but they vary a bit, like groceries or utilities and non-monthly would be clothing or gifts. After you tally those, you add them up and subtract from your monthly income. Hopefully, you have money left over, which would be either disposable income or savings. If not, you scream until you figure out what you can cut from your life. Actually, regardless, there will be internal screaming.

A seagull, after seeing his monthly clothing budget

Since I’m going into freelance without clients, my income would become me paying myself from my savings. Awesome because I can give myself a raise whenever I want to the detriment of my boss, me, who will simply ask more out of me, the employee.

Make a Plan

All right. I made the decision, I told people, and I created a budget. Now. What’s the plan? What needs to be done to start getting clients? I wrote things to do on Post-It notes:

  • make your website look professional, i.e. take down drunken rants from three years ago (but save as drafts; they are money)
  • find a domain name that isn’t stupid
  • start an Upwork account
  • research other avenues to find clients
  • start blogging
  • create more specs
  • decide what kind of work you want to do


Deciding on a domain name took me two days. Then I tried to redesign my WordPress site, which again took a lot longer than the 45 minutes I envisioned. “This theme? No, this theme? This theme? No, this theme? No, this theme.” Researching revenue streams took me down Clickbait Avenue. Trying to decide a niche for myself was another 48 hours of listing things I knew and then asking, “But do I really?” With a timeline of six weeks to get everything together and quitting my job, I needed a sense of urgency.

Rip Apart an Elephant

Do it

What’s the saying? It’s easier to eat an elephant by tearing it limb by limb than biting into the whole thing?

I’m pretty sure that’s it.

When faced with too many things to do, I freeze. To unfreeze, I broke down my to do list into bite sized pieces. I compared it to running. If I’m planning on a 45 minute run, that seems daunting. But if I tell myself to make it to the fifteen minute mark and then the 20 minute mark, then the thirty, it’s not so hard.

So, instead of just a “Organize WordPress site” post-it note, I broke it down into multiple post-it notes: “Draw website”, “Write Copy”, “Organize Pages”, “Write Specs. I accomplished two of those in the same time frame as it would have taken me to procrastinate by baking cookies.

If you hit the proverbial elephant with a grenade

Expect Good Things

Always expecting the worse has been my mantra for the last several decades. While this has given my humor a knife sharp edge, my negativity is exhausting and not much fun. Changing my outlook to positivity is a must.

Generally, people don’t dive into a pool expecting to hit their head on a rock and severing their spinal cord, rendering them a quadriplegic and becoming a burden to loved ones. Usually, as a diver arches their way into the shimmering blue water, they anticipate the cool splash and the suddenly absence of sound, replaced with the gurgling of water. Then you rush to the top, with all your limbs still working and your face breaks through the surface back into the world and you breathe that sweet, sweet air.

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