Reverse-Engineer Your Writing Career

Private sector → freelance is no longer the standard.

Freelancing has always been gatekept by vets of the private sector.

A style of living and working reserved for only the most experienced, the most accomplished, the most revered of professionals who’d cut their teeth for decades in cubicles before opting to work on a Bali beachside.

But low and behold, that paradigm has been shattered. The gatekeepers have left their posts.

Now you have 20-something freelancers absolutely killing it. They watch some Neil Patel videos, take a few LinkedIn Learning courses, get on Fiverr, dive into cold outreach, and voila — a new career is born.

All you need is a few well-paying clients to make it happen, after all.

That’s what I did

I went into IT sales straight out of college, cold calling 100+ strangers every day and pumping toxic amounts of Red Bull into my bloodstream.

It wasn’t my cup of tea.

I’d go home, my creative muscles aching to flex, and write some poetry or journal a bit to unwind. Writing kept me sane.

Then I found Fiverr — a place where you can make money with words. It’s also the perfect playground for budding writers with little experience.

It’s a freelancing platform that offers services at every level. You can pay pennies for garbage, hundreds for premium work, or get lucky with a cheap high performer. Which is why it’s a great place for fresh content and copywriters to launch their new careers.

Fiverr is where I started. From there, you can flaunt your work to private clients or even full-time employers, which is exactly what I did. Samples and social proof are key.

From freelancing to full-time

Trigger warning: I’d rather learn the ropes in the private sector than risk teaching myself poorly.

After Fiverring for a few months and landing a staff writer gig, I started applying for full-time copywriting jobs.

Keep in mind that at this point in time (mid-2021), when COVID was in full swing, the job market was tight. It still is. So people prioritized security.

With the portfolio samples from Fiverr and that magazine, I landed a FT role at an agency within six months.

I know that there are countless ways to teach yourself nowadays. YouTube, Udemy — you name it.

But I wanted to learn from the pros firsthand, before eventually returning to the freelance world with more weapons in my arsenal.

I think this is a huge hack that former generations could never leverage.

Bringing it full circle

Past generations could never start out freelancing and go full-time with the ease that we can. Thank you, internet.

You can hit Fiverr to gain experience, land some private clients, go full-time, then return back to Freelance Land once your confidence is set.

I’m currently in stage two of the process: working full-time as an in-house copywriter. I recently moved from agency to in-house.

After a few more years of skill-building, I’ll be ready to dive back into the freelance pool.

This is the power of the internet in the 2020s. You can start a side hustle today that grows into a replacement for your FT job.

It can be leveraged for dramatic career shifts, nixing sustained professional unfulfillment. Fiverr and my first private client are what/who I thank for getting me out of sales and into copywriting.

Now, I can’t imagine not writing for a living.

Which route will you take?

The freelance world is the wild west now. Thanks to platforms like Fiverr and Upwork, it’s never been easier for newbies to land paying clients (not necessarily a good thing, but if clients are looking for cheap work, that’s on them).

Then you can continue freelancing if things are going well, or go full-time for the experience and security.

Or you skip a step and start FT if that’s your goal. Maybe you did a few internships in college. This is far more difficult as a new content/copywriter with no portfolio or experience backing you.

That lack of social proof is why I took the reversal route. Now my words are salaried, and every day adds a new item to my portfolio.

Take advantage of this recent paradigm shift, because freelancing is no longer reserved for the vets.

Thanks for scrolling this far. I appreciate your read!

If you enjoyed the article, consider…

*Subscribing here

You’ll receive 3–4 articles per week on:

• Writing
• Digital/Content Marketing
• Mental Health x Workplace
• Communication
• A poem or two, if whiskey is around.

See you in your inbox!