Love Your Work, Make Enough Money, Have a Great Life

A 3-step guide to living how you want to live right now

I could begin and end this article with:

Listen to Tom Petty.

If more people realized how his music could help set their life straight, the entire self-help industry would go bankrupt.

Tom Petty’s work applies to younger audiences because it’s timeless.

Do you know when he released the universal classic, American Girl?

1976!

Given how that song still brings people in their twenties and thirties onto the rock and roll dance floor, you’d never have guessed it’s roughly 45 years old (just like me!).

Precursor to the three steps — treat yourself and your life like Tom Petty’s music.

You’re timeless. You’re “not affected by the passage of time or changes in fashion.” In other words, this is your place; you make the rules.

Don’t listen to your parents

Chances are they mean well. Some parents might even be cool and with it enough to know and give good advice to people twenty or more years younger than them.

If you listen to your parents, there’s a relatively high probability you’ll experience less than you otherwise would.

From my perspective —

Had I listened to my parents when I was 16, I would not have gotten drunk for the first time when I was 16. Getting drunk at 16 was one of my fondest memories. Neil Young’s Rockin’ in the Free World played as it happened.

Had I listened to my parents when I was in my twenties, I’d probably would be working a 40-hour per week job for some lame Fortune 500 company.

I’ve had a few career stints in this realm. And I hated it. I have only truly loved my work when it was physical and social (bartending) or when I called my own shots (freelance writing). Like I do now.

Had I listened to my parents, I’d probably still be in an unhappy marriage. The thought of “breaking up a family” didn’t quite sit well with them. They’re good with it now, but I knew I had to make the decision then tell them, not the other way around.

I’m not trashing my parents. They have always looked out for my best interests and supported me unconditionally.

But here’s the problem.

My 74-year old Mother and 86-year old Father can’t possibly know what the best interests are of a 45-year old man who has not lived in his small hometown since he was 19. The 48-year old and 60-year old iterations of my parents could not have possibly known what was in the best interests of their 19-year old kid with stars in his eyes.

If I had told my parents — when I was 19 — that instead of moving to Miami, I was going to marry my high school sweetheart and stay in my hometown, firmly entrenched behind a white picket fence with multiple toddlers running around the over-sized backyard, they would have been all for it.

Because it would have been in their best emotional interests, if under this hypothetical, they understood and appreciated my best interests, they would have said, “We would love for you to stay, but it’s probably not the best decision if you want to live the life you want to live right now” and into the limitless future.

Just as you do with articles on the internet, consider what your parents have to say. Maybe even use or adapt some of it. Respect them. Call them every day. Send pictures. Visit as often as you can.

But don’t listen to what your parents say, particularly if it will limit the breadth and number of experiences you have in life. Each experience builds on the one that came before it. And, before you know it, you’ll be experienced enough to be the one your kids would be better off not listening to.

Keep a low cost of living

This advice has become a personal financial platitude. This is because we wrap too many rules around it.

Among the most recurring — don’t buy coffee every morning. Some of the same people who tout this tired mantra, take no issue with your trip to Barcelona. They view going to Spain as an “experience” and the coffee habit a waste of money you could be investing.

Just as we require big experiences to grow and develop, we need micro experiences. Everyday interactions like the ones you have in the coffee shop — or out in front of the pandemic coffee shop — matter. They’re part of the theater of the city (or, to a lesser extent, suburb). They’re part of the rhythm of many of our lives.

If you’re not waking up next to someone every morning, the barista you have come to know might be the first person you interact with in your day. Take this seriously. On occasion, say something that’ll make their day. The inverse might hold true.

One recent morning when I wasn’t feeling particularly good about myself, the barista at my local coffee shop announced he was leaving the job. He said he wanted to let me know because he always liked seeing me in the morning and that I had “a good vibe.” I don’t feel like I come off this way at all. To hear those words — to receive that compliment — meant more to me than he knows.

This is one micro experience of the literal millions that occur every single day — heck, maybe every hour — in cities around the world. Some cost money — directly or indirectly. But they matter.

As I explain elsewhere and often, a low cost of living isn’t about not having a life. It’s about having a personal financial system that prioritizes allocating cash flow:

To be financially flexible, you need pots of money.

One pot of money to consistently satisfy your monthly living expenses for 1.5 to 2 months (subsistence fund). One pot of money to cover reduced or a total loss of income for 3 to 6 months (emergency fund). Other pots of money to pay for discretionary needs and wants (a new apartment or continuing education fund). And another pot of money to fund the aforementioned starts, stops, and restarts (transition fund).

Look at how much money you make. Aim to earn enough money to meet your expenses and have at least a little extra to work with at the end of the month.

Hopefully, you work in a capacity without a tight ceiling on your earnings (as in, you freelance in some fashion). Fill these pots of money (or pots like them) religiously each time you receive income. Before you know it, you’re financially flexible, especially if you maintain a thoughtfully low cost of living.

It’s also about making compromises:

Compromise isn’t a bad word.

It’s just a choice you make in one area to get something you want more in another.

Forgoing the coffee has no broad impact. If you balance it with having a day-to-day life where you relish the small things, saving that five bucks probably results in a net loss. It’s the big things that matter. Like rent.

I live in Los Angeles. I have a (great!) studio apartment in a gritty neighborhood that costs me $1,342.11 a month. My girlfriend lives a few minutes away — in a decidedly nicer neighborhood — and pays just slightly more for a one-bedroom.

We both compromised.

I didn’t opt for new construction in West Hollywood. That would have cost more than $2,000 a month. She took an apartment that needed work but saves her, at minimum, $500-$600 a month.

This is part of why we get along so well. We not only have similar outlooks on life, but we execute — not in the same way (that would be boring) — in the same personal financial ballpark.

Find the right partner

I loved what Kathrine Meraki had to say about “secure” relationships in a recent Medium article:

It’s easy for us to go from being together to spending time apart and being independent. When we feel secure within ourselves and our relationship, there’s no anxiety or fear around abandonment or someone getting ‘too close’…

Secure couples are okay with independence and togetherness. They also don’t get jealous when their partner hangs out with friends without them.

This matters so much as it relates to what you sort of, kind of need to make any or all of the above happen — money.

If you’re not generally secure in your relationship, to begin with, you’re going to create a toxic situation between you, your partner, and money. Money crushes partnerships as much as, if not more, than any other issue. If you can talk about it (and sex) honestly, openly, and without inhibition, you can talk about anything.

However, if you can’t master the notion of alone together in the broad sense, you’re not going to do it with money:

…we both understand we have to be good at being alone together. The idea that you can spend hours in the same room — together — doing separate things…

Instead of the binary do we keep our finances separate or do we keep them together, how about you keep them alone together?

Security in a relationship means, in part, that you don’t keep tabs on every dime that comes in and out of your partner’s door. It’s hardly different from not worrying if they’re going to cheat on you with an ex or somebody new who finds them attractive from across the bar.

You got into a serious, committed relationship with this person — the right person — so let it roll. If you’re lucky enough to have found the right person, and you forge an enduring partnership, you’ll stand a snowball’s chance in a warming climate of being a kickass team.

Two strong individuals coming together to get shit — to get life — done.

I try to view life through the lens of a feel-good pop-rock song:

But then she looks me in the eye and says “We’re gonna last forever” And man, you know I can’t begin to doubt it No, ’cause it just feels so good, so free and so right I know we ain’t never goin’ to change our minds about it, hey

— Tom Petty, Here Comes My Girl

One thing it took me just over forty years to learn is that to love your work, make enough money, and have a subsequently great life, you have to:

• Stop listening to your parents
• Maintain a thoughtfully low cost of living
• Find the right partner

This isn’t standard personal finance guidance. And this is because standard personal finance guidance doesn’t work. Personal finance is personal. It’s not one size fits all. Not even close. No two people can execute the same strategies with money.

You’re going to move money — spend it, save it, budget it, invest it, give it away — differently than I will. Even if you take a slightly different approach, there will be meaningful variation.

It’s the theoretical, approaching practical mindset you wrap around the pragmatic parts of yourself that matter.

Or you could just haul off and listen to Tom Petty’s entire catalog, on blast and repeat. Life will come together for you after a handful of fist pumps! You’ll figure things out just as well.

This article is for informational and entertainment purposes only. It should not be considered Financial or Legal Advice. Not all information will be accurate. Consult a financial professional before making any major financial decisions.