This as-told-to essay is based on a conversation with Jessica Winder, a 37-year-old senior vice president of HR for a Canadian tech company and career coach in Las Vegas. It has been edited for length and clarity.
In 2020, I worked two full-time HR jobs simultaneously. I already had one job going into the pandemic, and I decided to pick up a second. They were both fully remote.
With nowhere to go and nothing else to do, I figured — why not? After doing it for a year, I saved over $100,000.
At my first job, I was able to finish my work early and often felt bored
One night while watching TV, I thought: If I have the time and capacity, why couldn’t I take on another full-time job, without anyone finding out?
I didn’t know anyone personally who had done this. I’d heard of contractors juggling multiple gigs, but not salaried employees.
When I picked up the second job, it was always meant to be short-term. I told myself I’d do it for 90 days, save up some money, pay off my credit cards, and then quit one of them.
I applied via LinkedIn to several jobs and made it to the final round for two companies. I picked the one that seemed the easiest. In the interview, I just made it seem like I’d be leaving the first job.
The second job was always the one I planned to leave
I didn’t care about it. I cared more about the first one, where I’d been for a while.
Both of my jobs paid six figures. After reaching my first goal of paying off my credit cards, I thought, Well, they haven’t found out yet, so I kept going. I set a new goal to save $20,000.
Once I reached that goal, I continued to create new ones. I put some of the money toward my wedding, honeymoon, and relocation to Las Vegas, and I still have some of the money in my savings to this day.
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I didn’t change my lifestyle at all; I had the same car, apartment, and everything else. I may have eaten out more, but besides that, all of the money went into my savings account.
It was chaos at times
At one company, I was in a leadership role. I had enough autonomy to block time on my calendar — marking it as “hold” — so it wouldn’t raise a red flag. Still, it didn’t always go smoothly.
There was a day when I had to be in two meetings at the same time. One company required cameras to be on, while the other didn’t care. I set up both laptops: on one, I had my camera on and was fully engaged. On the other, I logged in and turned off both the camera and the sound. The whole time, I was so anxious, constantly worrying that one meeting might somehow hear the other one.
When I tell people this, they often say, “You know, you’re greedy,” or “That could have been someone else’s job.” I understand where they’re coming from, but my stance is also: They paid me to do a job, and I did it. I think you can have 10 jobs if you want to — if you’re willing to get the work done.
There were some pros and cons, too.
Pro: It gave ‘recession-proof’ income
During the pandemic, I saw a lot of my friends get laid off. That’s when I started thinking: If I have two jobs and one lets me go, I’ll still have a job. In my mind, that felt recession-proof.
That was the thinking behind it, and honestly, I still stand by that.
Pro: It was cross-training on a whole new level
In one role, I focused heavily on training and development, while the other was much more centered on employee relations. I was getting the best of both worlds.
That kind of cross-training just doesn’t happen in a single job. Normally, you’d specialize in one area or the other. By juggling both, I expanded my skill set in two different areas at once.
Con: It was a lot to balance
From 8 to 5, my entire day was packed with meetings, bouncing back and forth between the two companies. Then at night, I’d get the actual work done — splitting my evenings between company A and company B.
I often worked 12- to 13-hour days and kept it up for 12 months straight. There were so many moments when I’d be working on something and suddenly think, Wait — am I doing this for the right company? I was constantly switching back and forth.
I also had to constantly monitor my Slack messages — it was complete chaos. To this day, I still have Slack notifications turned off because just hearing that sound makes me anxious.
Con: Juggling time off was exhausting
This was during the pandemic, so it’s not like I was vacationing much, but when I did want to take PTO, I had to make sure it coordinated with both roles.
There was a time when I took a week off from one job, but I couldn’t take the same week off from the other. So it really wasn’t time off — it was a break from constantly switching between the two roles.
Would I do it again?
I quit the second job after 12 months, and now I have a different job, but I’m happy with just the one.
At this current stage in my life, now that I have kids, I wouldn’t do it again. I don’t have the time, but would I advise someone single, who doesn’t have kids, and does have the time to do it? Maybe.
But understand there’s a risk to it. If one company finds out, you could be fired from both jobs. You could keep it going for a year without anyone finding out — that’s what happened to me — but you could also get caught in two months and lose everything.
