Moonlighting In The Spotlight

Follow Your Passion (In Your Spare Time)

Over the past 2 years, I've been fascinated by the working from home (WFH) movement and the second order effects of it. For many, WFH has allowed workers to spend less time commuting and putting in face time at the office and spend more time being productive and doing things they are passionate about—such as playing golf, exercising, spending more time with kids, traveling, or running a side hustle.

Today, I want to talk specifically about side hustles, those who work multiple jobs, and those who do either while WFH. This post was actually inspired by a tweet I saw a few months ago from Jason Calacanis which has lived rent free in my head ever since.

On the surface, Jason's tweet has the "old man yells at cloud" aura to it. As if a vast number of people who are WFH are overtly taking advantage of their situation, to which he clarified in a follow up tweet that he didn't think the majority of people were abusing their WFH privilege. What if employers were the ones who were taking advantage this entire time and the power is finally moving back to the people?


While doing research for this piece, I was curious to see how many people had multiple jobs and the reasons why, and I stumbled upon this chart from the U.S. Bureau of Labor Statistics. Even though the chart is 25 years old and the sizes of the pie surely have changed since then, the overall reasons for moonlighting still likely hold true—particularly for meeting regular household expenses during 40-year high inflation.

According to the BLS, 4.8% of employed persons in the U.S. hold multiple jobs, with 430,000 of them working two full time jobs. Even though the percentage is near the all-time lows (sans the Covid drop), the total number of people with multiple jobs is at the highest level ever, from the beginning of the dataset in 1994.

The BLS defines a multiple jobholder as a person who had two or more jobs during the survey reference week, at least one of which was a wage and salary job. Self-employed people with multiple businesses and people with multiple jobs as unpaid family workers are not classified as multiple jobholders. Side hustles would also not be included in this dataset.

It's also interesting to look at the breakdown between primary and secondary jobs being part time vs full time. Multiple full time jobholders still represent a small portion or the total working class that has stayed relatively constant over the past 30 years.

As noted by Heidi Shierholz, president of the Economic Policy Institute, "Historically, the share of workers with multiple jobs goes up when the labor market is strong and goes down when the labor market is weak. It's basically a question of job availability. We are seeing this increase in multiple job holdings as the labor market has strengthened."

Additionally, workers have held multiple jobs just to make ends meet with inflation continuing to rage. According to a survey from Primerica, three quarters of middle-income workers feel their income is falling behind the cost of living. Many of the trends below are going in the wrong direction.

Depending on the role and market sector, one could argue the majority of workers take on multiple jobs because they feel they have limited control on their upward mobility at a company. Take for example a salaried employee who every year gets the standard bonus, standard raise, and can work anywhere between 30 and 60 hours a week. The only true incentive for them to go above and beyond is a promise of something better in the future—becoming a partner, climbing the corporate ladder, a bigger bonus, whatever it may be.

However, none of those promises are ever guaranteed and many workers waste years chasing one of these outcomes with an employer who never planned on giving it up anyways. Big corporations love these types of employees who just keep their heads down and accept the status quo without ruffling any feathers or asking tough questions, mostly because they know they can just be replaced.

One must look through the lens of an employer and as an employee and come to some sort of compromise. At the end of the day, employers want dedicated employees who work hard. The problem is it's tough and expensive to find those employees and even more difficult to retain the best talent. Smart employers want to keep their employees on a relatively tight leash, but give them enough slack so they don't choke. The compromise lies within the employer giving the employee enough time and freedom to follow their true passion and give them the creative outlet to explore entrepreneurship.

Follow Your Passion (In Your Spare Time)

How many people do you know who went to college for a degree that they currently don't even use?

A recent survey from Finder shows about 2 in 5 people don't use their college degree. Why do you think that is? My guess is it's a combination of indecision of what they want to do in the future and because they were told to follow their passion as they were growing up. What those mentors neglected to tell them is that for the vast majority of workers, passions don't typically pay the bills.

Imagine your art teacher in high school telling you to go to college to get an art history degree. You go to a prestigious university for 4 years, then graduate with +$150k of debt and a salary in a field that can never substantially work down that mountainous debt load. At this point you only have one choice, take the only job available at the time to start paying off your debts—often times leading you down a completely different career path and abandoning your passion altogether.

In a talk about his book The Algebra of Happiness, Professor Scott Galloway goes off in the video below about the career myth advice of "following your passion" and how he thinks it's complete bullshit.

I hate to say it (because it's cool to fade him) but I agree with Galloway. You have to first follow what you're good at, then make time for your passion. Do your passions on weekends and nights to fill that gap. Then, when the unit economics on your side hustle start to become more attractive and close replicating your full time wage or salary, you can turn your passion into reality.

Moreover, having your passion as a side hustle allows you to take advantage of certain employer-provided benefits such as health care and retirement plans without the added cost or risk.

Encouraging Entrepreneurship

Going back to Jason's tweet at the beginning, there's a feeling out there that employers should expect their employees to be fully committed to the task at hand. That's noble, but also unrealistic in today's exceedingly digital and connected world.

Employers should be encouraging entrepreneurship for a multitude of reasons. Every job or career will be lacking something—pay, growth, excitement, soft skills, sales, etc. When employers encourage and allow their employees to have side hustles, it allows a creative outlet for the employee while the employer acknowledges the missing gap within their own culture. The result is a happier and more fulfilled employee.

What really matters at the end of the day? Having reliable and productive employees, not disgruntled ones.

During my time supervising younger folks, I have been clear with many of them from the start. Get your work done when it's due. If you get it done in half the time and I don't have more work for you to do, then I don't care what you do for the remainder of the time. Go take a nap. Go for a walk. Play video games. Do something that makes you happy. But come back ready to work again when the time comes.

You're probably thinking that sounds ridiculous. Give them more work. But people forget how much downtime and fluff there is in any given day. When this exact situation occurs in the office setting, you typically don't have those luxuries of doing something you enjoy. Instead, you're stuck on your computer screen, doomscrolling through social media or reading the news—arguably unhealthier habits—which leads to mental fatigue and disgruntled employees and the ouroboros continues.

Instead of condemning employees for pursuing their passions, employers should embrace the entrepreneurship and give more freedom to retain the best talent.