My Story of Working Two Full-Time Remote Jobs

A story in the Wall Street Journal caught my eye with the headline, “These People Who Work From Home Have a Secret: They Have Two Jobs.”

That was me. Two full-time 6-figure per year salaried positions. It lasted exactly one year before they both found out. What happened, why’d I do it, and would I do it again?

Read on, friends.

In early 2020 I found myself in the job market. I was looking for account-based marketing positions but in January was contacted by a recruiter who had a client with a demand-gen position open. I applied and got the gig, which required me to be in the office once or twice every couple of weeks. This was a mostly remote position even before March of 2020. In February one of my ABM applications had gotten noticed by a fantastic tech company with a 100 percent remote workforce. Wouldn’t you know it, I got the offer from them and considered leaving the demand-gen role for the ABM one.

But then I thought about it. I ran a marketing agency for nearly 10 years and handled multiple clients on my own. Why would this be any different, I thought? I could handle two “clients.” Especially with fully remote work and no limitations on workday hours. Why would it matter if I built a webinar at 10 pm instead of 2 pm, so long as it was finished and ready by the deadline?

To be clear, I checked the contracts of both positions and both mentioned that outside employment was acceptable so long as it didn’t present a conflict of interest. These positions were in completely different industries so I truly believed I was okay.

So in March 2020, as the world was shutting down, I was ramping up. Yes, I had to juggle call schedules during the day and play some Tetris with my calendar. But I did it. For 12 months I collected 4 paychecks per month and met my obligations to both companies.

That WSJ article mentions how some people worked two jobs but only put in 40 hours a week combined. That was not me. I gave both jobs as much attention as they needed and yeah, it meant some early mornings and late nights. But it was my life at the time and I enjoyed it.

We saw success, and challenges, at both companies but worked through them. I had some personal drama unfold at the time but dealt with it and had fantastic support from my team and my leadership.

There’s a David Ogilvy quote that I loved since my agency days that says, “I never tell one client that I cannot attend his sales convention because I have a previous engagement with another client; successful polygamy depends upon pretending to each spouse that she is the only pebble on your beach.”

That was my mantra. No missed meetings, and full devotion to each job; just often not in the traditionally “accepted” hours of work.

In early March of 2021 my employer at Job 1 needed another me; someone to handle demand-gen for a new pillar of the company. The recruiter who found me for that role had checked my LinkedIn page and saw a different position listed. She called my boss to ask if I was still there. He said yes, she mentioned my LinkedIn page, he checked it, and called me.

I came clean and told him I’d been working for the past year with another company, but in a different industry. My boss at Job 1 called my boss and Job 2, told her about my “polygamy,” and, well, that is the day I went from making high 6-figures to making zero figures.

It’s also the day I realized the world of work has changed, even if the concept hasn’t quite caught up with employers just yet. Covid has taught us that we don’t need to be confined within four company-leased walls and work defined hours to get a job done. Employment is no longer an exchange of money for work completed in a defined 8-hour period. It is an agreement to trade money for working toward and achieving company-defined projects and goals. Yes, meetings and Zoom calls often need to happen within traditional business hours. But if an employee decides that his or her best work will happen at 11 pm, after getting the kids settled or after handling other obligations, why is that a problem? Why are we focused on time served versus projects completed?

I’m proud of what I accomplished in that year and have no regrets about working for both companies. I adore the people at both and hope both achieve every goal they have set for themselves. I had good relationships with the leadership of both firms and appreciate the love and support they gave me while I was there.

Given the opportunity, I’d probably do it again. I’m proud of my entrepreneurial spirit. I know that my knowledge, skills, and experience can be useful to growing companies. I realize that posting this will probably severely limit my potential for future full-time employment, but that’s fine. I’m a go-getter, I have high expectations for myself, and I know that the right people and/or organizations will appreciate that.

What are your thoughts on holding multiple jobs or working non-traditional hours?