What Working Two Jobs Taught Me About Life

There’s something to be said for working a second gig. Let’s discuss.

James D. Blythe
13 min readJul 17, 2023
Image generated by author via Midjourny (2023).

From the desk of James Blythe —

I am a firm believer that people should avoid being too comfortable. Being comfortable makes you soft.

Yes, I am aware that sounds stupid. Yes, I am aware this is not a popular sentiment among polite company.

Big problems happen when you start taking things for granted. Whether it is your friendships, relationships, jobs, or other aspects of your lifestyle… disaster strikes when you get cozy.

The premise of our discussion today is that working hard is good. No, this is not a “make mo’ money” talk. It’s a “lessons learned in trial-by-fire” talk. Working multiple jobs taught me fundamental lessons about life that every person should be equipped with.

I’d like to impart upon you a few of these lessons that I’ve picked up over the years.

At a time when Americans seek comfort in life, working more can help bring “what’s important” into better focus.

A general consensus seems to have emerged that this generation of Americans will be worse-off than the previous two due to the rising cost of living (COL) outpacing wages.

I’m not completely sure that the data supports that COL is out of control (on average)…

…that being said, there are certainly some less-than-ideal numbers here worth considering.

The problem with this narrative is that Americans casually accept “we’re fucked” based off the say-so of people who have a vested interest in selling you content to “un-fuck” yourself.

Blog posts, YouTube videos, and books are published every day that advocate young people give up and get out of the rat race. [1] Do a search on Medium right now and see what pops up.

Go ahead, I’ll wait.

The premise of these doomsayers is usually, “the system is rigged and you will never be able to get ahead. Why bother grinding now? Live for today!”

“Don’t work that second job!” They tell you.

“Stop working overtime!” They scream.

“The 40 hour work week is tyranny!” They declare.

“Take your life back!” They urge.

I disagree. Working hard got me to a place in my life where I’m financially secure. I’m also on a trajectory to retire comfortably, though not exotically.

My situation isn’t particularly unique. I like to think I’m a modestly competent engineer and I make an effort to be a passably decent person. I don’t own a business. As of the writing of this article, I don’t “monetize” anything.

I’m a working stiff.

That being said, I usually work more than 40 hours a week. Historically, I’ve worked more than one job at most points in my life. At minimum, I do some extra contracting work outside of my standard office-hours.

It hasn’t always been fun. It has often been uncomfortable. It has occasionally been unpleasant.

In return, however, I’ve gained invaluable life skills by being a little more ambitious and working a little harder than my peers.

Most importantly, working multiple jobs taught me to live life with intent. It forced me to be honest with myself about what is essential for living and what is unnecessary bullshit.

The financial incentivizes to “work more” have been endlessly espoused by the internet’s legion(s) of productivity gurus. What I’d like to focus on are the other skills and intangibles that I picked up during this journey. Hopefully they are of some value to you, dear reader.

When I was twenty-something, I had no lifestyle. I’m still not sure I know what “lifestyle” is.

Before we get started, some background...

I spent my twenties working 2.5 jobs and going to school full time. College is not the solution for everyone. That was the path I took to get where I wanted to go.

I ground hard from 0500–2300 five days a week between school and whatever corporate name-tag I had on to pay rent. On the weekends, I worked a third(ish) gig but it was usually only a half-day commitment (5–6 hours) so I got to catch up on sleep, finish my homework, and do my household chores.

That was life. As in, that was my entire life. [3] I had a goal — to stop living hand-to-mouth — and that’s what it took to get to it.

This went on for close to four years. I worked retail. I bartended. I waited tables. I even did contract gigs working sporting events for small event companies and the local university. Whatever it took to make a buck.

Once I graduated, I got my first engineering job. Mission accomplished! Time to relax and reap the rewards, right? I had arrived!

Not quite.

I was putting in between 60 and 70 hours a week at the office. The long hours weren’t compulsory. It was what I needed to keep up as a new engineer. I still did gig work on the weekends. By the time you accounted for work travel and the other logistics, I was working as much or more than when I was in school. The big win was I had a more regular sleeping schedule.

I didn’t see much upgrade to my lifestyle. I drove the same bum car. I still cooked meals at home. I didn’t really take vacation. I did my own taxes. I got my coffee for free at the office or from a pot at home.

And life has continued on since. I’ll spare you the rambling role of events.

This is just to say that for those of you reading who are early career professionals that lament having a full-time job and not being able to live the way you want. That’s normal. In my experience, life is lean for a very long time. Don’t despair.

I learned a lot from the struggles in those early years. Those lessons have helped define who I am and taught me to live with intention.

But Mr. Blythe, no one ever looks back at their life and says, “gee, I wish I’d spent more time at the office!”

Image generated by the author via Midjourney (2023).

That’s probably true. I personally can’t think of anyone having uttered those exact words either.

Long walks on the beach, afternoons with family, and leisure activities of their ilk are worthy events in your life. That being said, I don’t believe that working hard, living life, and “making time for what counts” are mutually exclusive.

Three common regrets I hear from retirees or near-retirees are —

  1. Regret not having worked hard enough to afford to live how they want.
  2. Regret missed career opportunities to do cool things.
  3. Regret missed opportunities to work harder when they were young so they could make time for family now that they’re older.

No one wants to spend time at the office. No one wants to work two jobs. We do these things because they get us to where we want to be.

Be careful about accepting the “skip the office and live for today” mentality. Certainly, we need balance in our lives but working hard is a critical component of a life-well-lived. It certainly has had financial benefits for me, but it’s also set me up with the skills and experiences to know when to get out of the office and make time for important things.

Here is what working those long hours while young has brought to my life. Lessons I’ll never forget.

Working multiple jobs teaches a person their limits.

This is an unfortunate consequence of living hand-to-mouth and working more than you reasonably should. You learn some hard truths about what you can handle and what you can’t.

How long can you eat instant ramen and eggs for every meal before the taste of it makes you gag? For me, it was a touch short of four months. Curiously enough, the experience also taught me the basics of cooking. There are an alarming number of ways to prepare those two simple ingredients.

How long can you go sleeping less than five hours a night before you completely fall apart? For me, I needed a recharge at least once every six days. I go further with proper application of caffeine, but things start to get weird, quick.

What you learn is that, as a person, there’s a lot you are capable of achieving and enduring. You know when to push yourself and when you need to pull back. It teaches what things you can go without and what you can’t.

People say “can’t” when they really mean “I don’t want to”. People work themselves until they pass out at their desks. Sometimes for months on end. There is no nobility in either. Know your limits.

That’s powerful knowledge.

Working multiple jobs teaches a person what material items are necessary and what are not.

When you are exhausting so much of your time, it makes you reconsider how much enjoyment material things really bring you.

Is that $4 cup of coffee bringing you that much enjoyment? Is that pair of shoes worth what you are going to give up to get it? What about the bag of chips or large fry? Did you really need it? How much value did you receive when you paid the Door Dash delivery fee for something you could have picked up yourself?

You want the brutal hours you’re working to have meaning. You want it to have an impact that lasts longer than your morning caffeine fix. These questions encouraged me to find avenues of fulfillment in life that didn’t require writing a check.

If you can successfully navigate your needs and wants, working hard and being frugal is a powerful life tool. Most of what people think they need to be happy or functional is actually superfluous. This will also help you avoid getting stuck in the rat race of the ever-expanding-lifestyle.

The more of these unnecessary things you can strip away, the more power you have over your life.

Working multiple jobs teaches a person what their time is really worth.

A rationale I frequently hear for eating out, or paying for convenience services, is that, “my time is worth more to me than doing it myself.” I hear this a lot when talking about cooking at home versus dining out.

This is rarely true.

Working multiple minimum wage jobs taught me that — regardless of how highly I thought of myself — there were few (if any) tasks truly “not worth my time”.

Some people look at this as a depreciation of self-worth. That’s incorrect. The value of your time is not defined by the wage you are earning. Seemingly trivial tasks can be more valuable than the dollar amount you affix to them.

This encouraged me to learn practical do things myself. What could I fix with my own two hands? What can I do myself to avoid paying someone else? I was spending a ridiculous amount of time working to achieve my financial and professional goals. Why would I give a chunk of that away to someone else needlessly?

Once I understood the true value of my time, I learned a lot of new skills. I learned to find enjoyment in mundane chores that other people disdain.

A few highlights include cooking, changing my own oil, basic maintenance of tools, how to be a savvy consumer, the most efficient way to clean up a house and kitchen, how to say “no” to more, doing taxes (manually), learning to be bored, how to whittle, how to use structural adhesives, how to use the right tool for the task, and how to fix a computer.

Working multiple jobs teaches you to be purposeful with your spare time.

Image generated by the author via Midjourney (2023).

I agree that the 40-hour work week is a time-suck. It goes above-and-beyond the hours in the office. It’s the commute and waking up and getting ready and spinning down and everything else.

“There’s not enough time in the day,” is a common refrain you might hear.

In reality, most people are inefficient in how they allocate their time. They wake up slow. They watch YouTube shorts for a couple hours. They meander around. When they get off work they spend time fussing over the day they just had and what they have to do next.

I know a lot of people think “this is what’s wrong with America, you can’t even take time to smell the roses!”

If you feel these sorts of things are necessary expenditures of your time, so be it. To me, they are luxuries. Luxuries are enabled by living in a manner well within your means which allows you to be wasteful (in a good way).

When you work multiple jobs, you can’t afford temporal waste. You learn to compartmentalize things in your mind and omit the unnecessary to make time for what matters.

I would eliminate unnecessary things so I could spend that spare time where it really mattered. With friends. With family. Reading a good book or enjoying a discount cigarillo at the end of the day. If I could get through my mandatory daily tasks quickly and effectively, I could carve out time to relax.

Normally, people don’t have to make these kinds of decisions. They don’t have to prioritize “what is important”.

The scarcity of free time brought on by maintaining multiple jobs teaches you to be thoughtful about how you spend the time you do have. Don’t waste. Use it on the things that are important to you.

Why would I ever want to work multiple jobs if I didn’t absolutely have to?

When your extra gig is not necessary for your survival, but you force yourself to do it anyways, some interesting things happen.

You get to experience “saying no”. Most people can’t walk away from a paycheck. They must do any menial task requested because it puts food on the table. If your “second job” is not paying your rent, you can experiment with when-and-how you say “no”, professionally.

I learned this teaching at university. Being an educator is a wonderful and fulfilling experience. I highly recommend it. Academia, like every job, has numerous non-value-add tasks that must be completed and egos that must be stroked to stay employed. “Fill out this survey, attend this seminar, go to this meeting about new financing rules for building fences at the rec facility,” what does any of that have to do with teaching students?

So I said, “no”.

They said, “you have to.”

I said, “no I don’t.”

They said, “it’s a condition of your employment.”

I said, “that’s fine, let me know when I need to clean out my desk.” Oddly enough, that phone call never came.

As a teacher, my primary goal was to provide value to the students. If teaching had been my primary wage-earner, I wouldn’t have been able to do that. I would have had to service the university first.

You can try a passion project without compulsion. People will tell you, “if you make your hobby your job, it will suck all the fun out of it!”

I have absolutely made passion projects into paying gigs and had a blast. The secret, however, was that there was no pressure for them to pay my bills.

Some people will argue that this isn’t really “working an extra job”. I disagree.

Just because you enjoy it, doesn’t mean it isn’t work. If you’re getting paid (or trying to get paid), maintaining a semi-regular schedule, and you’re providing value for a customer, I consider that working.

You won’t be starting a multi-million dollar venture with this strategy, but if you’re doing it for your own entertainment and a few extra ducats, then who cares?

An extra gig lets you learn new things. If your secondary isn’t your passion project, it’s still a great opportunity to learn. Every job I’ve worked has taught me a valuable skill and exposed me to people I might not normally cross paths with.

Teaching taught me how to communicate with and manage students. MC-ing weekend sporting events taught me how to be the public relations face of an organization. Aside from learning to mix drinks, bartending taught me how to efficiently serve customers and read people. Waiting tables taught me attention to detail and common courtesy. Retail taught me not only how to ten-key, but how to take pride and fulfillment in a job well-done even if you couldn’t care less about it. [3]

These experiences also give you an appreciation for people in different walks of life. Both your coworkers and your customers. That is a crucial life skill in itself.

Wrapping things up…

Image generated by author via Midjourney (2023).

In an age where popular dialog perpetuates doom-and-gloom, there is value in shaking off the ennui and “getting after it”.

Consider not just the financial benefits of “doubling up”, but the valuable life lessons and skills it will confer upon you. Those who are smart can learn these lessons without having to take on the pain of a second (or third) job.

Me? I had to learn it by living it.

As a result of this trial-by-fire, I now have a better feeling for who I can count on to “get after it” and who is inclined to work at their own convenience. That has served me well in my field and in my life.

For those who live the multi-job work-week, I feel your pain. Make sure the hard work you put in today is setting you up for a better tomorrow — whatever that looks like.

Young people shouldn’t judge themselves based off the comforts and status of others. Certainly not the older generation. Old people have had a lifetime to accumulate stuff — to save and invest and win and lose and make mistakes and benefit from unexpected windfalls.

It’s okay to be uncomfortable. Each individual cuts their teeth on the challenges that face them. There are lessons learned in hard work that are timeless. Take comfort in the fact that we will be right here with you, burning the candle at both ends.

As always, good hunting.

References and Footnotes

[1] Not to be republished here.

[2] Okay, you got me. Every other Wednesday I got together with a buddy at the local bar where they had half priced beer and chicken wings. I would order one beer and one plate of wings while we played dominos. This activity took the place of my regularly scheduled meal as I could not afford, and did not have time, to eat dinner and attend this event.

Occasionally a regular, my friend, or the proprietor would pick up a second (or third) round for me. I am forever grateful to those wonderful people and the fantastic memories during a very challenging time in my life.

[3] Of course, my engineering and fabrication gigs have taught me plenty of program management and trade-skills as well, but those remain in my primary career path so I’m neglecting to get into that here.

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James D. Blythe

Bringing an engineer's perspective to topics in technology, business, lifestyle, and other such nonsense.