A Gig Worker’s Letter to My Younger Self

Jeff Davis
3 min readJan 5, 2021
Photo by Scott Graham on Unsplash

Hey Jeff, I hope this email finds you well (that’s how we begin emails in 2021, you’ll see why).

I’m writing from the future, 15 years since you started your Baltimore PR company JD/PR, and yes, I’m still in the public relations business and enjoying this roller coaster ride you started.

A lot has changed in marketing and PR. MySpace has been replaced, thousands of journalists have been laid off and newspapers are closing. In the world of politics, a reality TV host (the one with the incredible ratings) was elected president.

Even worse, we’re battling a deadly global pandemic. The good news is your skills and ability to work remotely are the perfect setup for what we’re dealing with today. You made the right choice, but here’s what wasn’t so clear when you took the leap in 2005:

No two days are alike. The traditional work world offers a predictable routine, from the daily commute to the awkward Monday morning staff meetings. In the on-demand workforce, the workday has a different feel that you will get used to. Time is now in your hands and it’s up to you to make the most of it. If you want to start your day at 6:30 a.m. and take a workout break at 10 a.m., you can.

You’ll experience heavy focus and concentration. No more impromptu gatherings in the conference room to surprise Becky with birthday cake. Or the random “got a minute?” appearance at your office door. Depending on your work-from-home arrangement, your days are intensely focused and you can get much more accomplished in shorter bursts compared to the old days.

That check? It’s not all yours. That $5,000 payment feels good and validates why you made the leap. But wait, it’s not all yours to keep. The government wants a big chunk, and if you don’t set some aside, tax time will be especially difficult. We didn’t get into the PR business to satisfy a love for accounting, so one of your best investments is a financial advisor — not just a bookkeeper — who can advise you in ways far beyond your rudimentary business skills.

Get it in writing. Everybody says you’re a nice person, but that will burn you if you’re not careful. While you’re OK moving ahead with a handshake, don’t. Prepare a detailed scope of work and written agreement outlining tasks and payment terms. Get it signed before you dive in. For retainers, bill at the beginning of the month for that month’s work.

The freedom is priceless. No matter the ups and downs, the delays in payment, the crazy requests, nothing can replace the freedom you earned. Since 2020 we’ve been dealing with a deadly global pandemic that has caused offices to close. The good news is those of us living the gig-worker life are in a better position. We can work from anywhere and companies now realize they can hire based on talent, not location.

Enjoy the ride,


P.S. For extra cushion as you get things started, the Powerball numbers for Dec. 31, 2005 are 4 30 37 43 46 42

Originally published on the CareerGig blog.

Jeffrey A. Davis, APR has more than 25 years of experience in positioning and reputation management, particularly in media relations, media training, crisis communications and social media. He is founder of J. Davis Public Relations, LLC, a PR consultancy based in Baltimore, Maryland and is a frequent speaker on social media, PR measurement and crisis communications.



Jeff Davis

Public relations, social content and crisis communications insights and ideas from PR consultancy leader and co-host of the Practically Social podcast.