The Best Job Advice I Never Got
"These are the days you'll remember..." 10,000 Maniacs
I’ve been looking at business opportunities. It’s what I do. I get turned on by evaluating a Profit & Loss statement like some people get turned on by... well, let’s not go there.
I’ve owned two businesses and dabbled in a few solopreneur ventures, but lately, I’ve been searching for a new challenge. And once you realize that businesses, at their core, are just a series of similar tasks and challenges—buying inventory, managing cash flow, dealing with customers—you start to see opportunity everywhere.
Which is why, in the past few months alone, I’ve seriously considered:
A wide size shoe store
A furniture store
A bagel wholesaler
A bistro
A wood products manufacturer
A med spa
All of them were profitable. All of them presented unique opportunities. So why haven’t I picked one?
Because I’ve been experiencing a kind of FOMO—not the fear of missing out on an opportunity, but the fear of picking one and, by default, saying no to something better.
Which, if you’ve ever been on a dating app, you’ll recognize as classic swipe-left syndrome.
The Fear of Commitment (a.k.a. Business is Like a Dating App)
It’s easy to get caught in the endless loop of "But what if something better comes along?"
If I buy the shoe store, what if next month a boutique hotel I’d love more comes on the market? If I go all in on the bistro, am I saying no to the manufacturing business that might have been my perfect fit?
It’s the same analysis paralysis that keeps people endlessly swiping on dating apps. You go on a good date, but you hesitate to commit because—what if someone better is just one more swipe away?
On the other hand, if you keep holding out for Mr. (er, um) Business Perfect, you might end up waiting forever—always looking, never landing.
So, what’s a girl to do?
How do you commit—whether to a career, a business, or any major decision—without the constant fear that future you is going to look back and say, “Wow, you really screwed that one up”?
And yet, there’s no way to predict the future. No way to guarantee that a decision made today will still feel right five years from now.
That’s when I realized the best job advice I never got.
The Best Job Advice I Never Got
For most of my career, I chose jobs and businesses based on what I thought they afforded me—whether in lifestyle, income, prestige, or location.
I went into banking because it was in a city I always wanted to live in (Amsterdam) and paid well.
I bought my hotel because it allowed me to live in a beautiful place while raising my kids.
I started other businesses because they fit a particular lifestyle I wanted at the time.
On paper, these seemed like great reasons. But there was one critical factor I never gave enough weight to:
How will I actually be spending my days?
Because the reality is: most of the benefits of a job or business are fleeting.
The prestige of a title fades. The excitement of a new venture wears off. The money stops feeling new once your lifestyle adjusts.
But how you spend your days? That’s your life.
I look at the wide shoe store I considered buying. Profitable? Yes. But then I picture myself spending my days talking to people about arch support and bunions and suddenly, my decision is clear.
And yet, this is the mistake so many of us make. We choose careers based on what they provide, not on what they actually require of us day in and day out.
The Illusion of a "Good Job"
Most people assume that a "good job" means one that pays well, is stable, and carries prestige. But have you ever actually considered how many of those "good jobs" involve a terrible day-to-day experience?
Being a lawyer sounds prestigious, but most of it is reading mind numbing documents, endless paperwork, and insane stress levels.
Consulting - really interesting work, but you also need to love an endless string of hotel rooms and airports.
Being a surgeon pays well, but it also means being on call, 5 a.m. rounds, standing for hours, and almost no flexibility.
Being an investment banker means big bonuses, but it also means you better love number crunching, 80-hour workweeks and constant burnout.
Most careers have a shiny outer shell—but the actual experience of doing them every day? Not so glamorous.
How We Spend Our Days is How We Spend Our Lives
So what does this mean if you’re facing a career or business decision?
Instead of asking, “What does this job/business afford me?”, try asking:
✔️ What does my day actually look like if I say yes to this?
✔️ Do I enjoy the daily work involved, or just the end result?
✔️ Will this choice still be fulfilling once the initial excitement wears off?
Because at the end of the day, your life isn’t made up of milestones—it’s made up of days.
The best job advice I never got? Don’t choose based on perks. Choose based on how you want to spend your time.
So, Am I Buying a Business?
Maybe. But the lens I’m using to decide has changed. It’s no longer about potential profit alone—it’s about whether I can genuinely see myself enjoying the work of running it every day.
And I’ll leave you with this:
If you’re feeling stuck in a career or business decision, stop thinking about future you. Future you is a stranger. Focus on present you.
Because how we spend our days? That’s how we spend our lives.
Well said! And such beautiful food for thought...... makes me ponder