better work newsletter #37

Google Guy: "You're highly hirable. You could go anywhere you want. Like Google."

Me: "Oh, yeah? What role would I have?"

Google Guy: "We'll find something for you."

This exchange happened at a meetup for entrepreneurs. I wasn't looking for jobs, and Google Guy wasn't hiring.

While I'm not going back to tech, it was validating to know that what I've been building for the last 10 years is working: a career that's neither traditional employment nor traditional entrepreneurship.

Bear with me a moment, and I'll expand on that. This year I was approached with:

• An invitation to apply to Google
• The position of Board Vice Chair at a non-profit
• A consultancy for a wellness startup on their systems

I didn't ask people to hit me up if they knew anyone looking for these services. These opportunities weren't even on my radar. And with each one, they approached me. It was often because of a face-to-face conversation that wasn't about work.

That interaction got me thinking about what actually makes a career 'work,' which brings me to Part 2 of what we covered in Issue #36, "Should you quit your job?"

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You quit…now what?

In part 1 of the "Should you quit your job?" series, we tested your readiness to resign by asking 3 questions:

1. If all income streams stopped today, how long will it take for you to be bankrupt?
2. If nothing changed a year from today, how would you react?
3. What does your ideal day look like?

Today we're wading through those post-quit waters together. When we think about careers, we usually think in binary terms: work for someone or work for yourself.

Since COVID, more people have embraced a third option: doing both. There’s also a fourth option of opting out of traditional pathways altogether.

You won’t know which is exactly right for you without experimenting, but understanding the benefits and tradeoffs of each can inform your experimentation for the better.

Let's start with corporate employment because it tends to get a bad rap. (It’s also where most of my readers are or started.)

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Corporate life is livable, for some

We know 9-to-5s have had the reputation of being unbearable at least as long as Dolly Parton and her jolly crew of corporate haters sang about it in 1980.

That cultural positioning solidified in the 90s with movies like Office Space and calcified with the anti-hustle movement of the 2020s.

Now, I hope you're sitting down because I'm going to share something shocking:

Corporate life can be pretty sweet.

Lots of financial perks and a fairly predictable workflow. Some people thrive in corporate environments because they don't need work to provide identity, meaning, autonomy, or self-expression.

Take my husband, for example. He shows up to corporate, does his job, leaves, and moves on with his day. He deeply cares about his patients and his work as a physician, but he doesn't put the full weight of his fulfillment on it.

Being a doctor is an identifier for him, not an identity. He's not the type to correct others with, "Actually, it's Doctor Susan’s Husband."

Of course he has complaints about his job. But overall he's perfectly content with riding it out for the next 20 years and collecting that sweet pension.

That arrangement works for him. I could never (though I secretly wish I could sometimes). The joy of being a professional clown on the internet is my siren's song. 🤪

If you're someone who similarly does need work to provide meaning, autonomy, or creative control, you'll likely find yourself eyeing the exit - and self-employment is usually the first door people open.
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Entrepreneurship isn’t an exit

The cultural promise of entrepreneurship is freedom. But the reality is you trade one boss for many: clients, corporate sponsors, investors, algorithms, quarterly tax payments, and the most difficult-to-please overseer of all - yourself.

The real benefit of business ownership isn't freedom from bosses - it's freedom to choose your constraints.

Take the archetypal YouTuber raking in millions from ads and sponsorships. To the outside world, that's the pinnacle of autonomy - until you follow the money.

The paychecks don't come from a vacuum. They flow directly from institutional balance sheets: the Fortune 500s, the VC-backed unicorns like Surfshark, the DTC disruptors like Bloom.

The check goes from bi-monthly to sporadic invoices, but the structural reality remains. You switch from being inside the corporate machine to being connected to it.

When you pull back the business curtain, you'll see that the largest contracts that actually keep the lights on are with corporations.

And that’s fine. We all need to get paid. The main difference is whether you thrive within your self-imposed constraints, or if their burden makes you miss the days when you could just clock out.

Responsibility is hard to hold alone. Entrepreneurship is no magical trapdoor. There's no team to delegate to. No HR to handle the mess. No manager to blame when things go sideways.

So, I get why people go back to corporate after running their own business. There's a distinct relief in having a single job.

Which brings us to the question that keeps hitting my DMs: can you do both?
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All of the above

Can you sit through the 9-to-5 for the steady paycheck and still build something that’s yours in your 5-to-9?

There are two obstacles with this doing-both option:

1. Your time and energy are limited. Not every hour of the day is created equal, and your most productive times might run counter to when you have time. The excitement of starting something new will fuel those 12-hour days for about three months. Then the endurance game begins.
2. Your brain turns against you. In corporate, you know when you're done. Entrepreneurs don't have that luxury. There's a perpetual 'What's next?' Success is ambiguous, a high-performer's nightmare. Add loneliness to the mix, and you've got a recipe for burnout.

Which brings me to the conundrum at the heart of all this:

A traditional job is stable until it isn’t. Entrepreneurship is unstable until it isn’t.

That's the tension: trading one kind of uncertainty for another. Choosing both limits your time, but increases your options. You're not desperate. You can say no to bad clients and hold out for true alignment. You can build slowly without the weight of 'this has to work or I'm screwed.'

I've watched dozens of clients find clarity here. The hybrid space let them create something of their own, find fulfillment outside their day job, and de-risk the leap through experimentation.

Once the thrill fades and the pace slows, how long can you keep going when nothing is happening?

That's where I come in. My role as their coach is less about strategizing and more about grounding them, swatting away the bullshit their brains feed them, and strengthening their tolerance for ambiguity.

None of the above

The truth is very few people end up where they imagined they would. They don't stay corporate forever. They don't build a 7-figure business overnight. They don't neatly fit into the molds we’ve been handed, or a hybrid of both.

We non-traditionals cobble together a fourth option, and that's the option nobody talks about. It doesn't have a sexy name or a TikTok trend.

The fourth option you have is dropping the arbitrary rules of what a career is ‘supposed’ to look like and defining success on your terms alone.

Some call this a portfolio career. I think we've gotten carried away naming things.

The term ‘portfolio career’ cuts out the essential yet non-career things - pottery classes, breaks for childrearing, profitless side projects.

Sometimes the answer is following the serotonin and saying, “This works for me right now.”

That, despite a culture that worships scale and optimization, is enough.

I've seen this work before. My friend started her own business, and then she made a podcast with a friend. Later, she was approached by a startup for a fractional role.

She's also on the board for a non-profit and posts LinkedIn content about her cat. Rather than one thing defining her career, she has a series of side quests.

Most importantly, she enjoys her days. She's proof the cliche is true: follow your fun and things fall into place.

Google Guy didn't find me through a job posting or a headhunter. He found me through a conversation that had nothing to do with work. That's the thing about building a career that fits.

You can attract the right people once you stop performing and start showing up. That's the muscle we build inside Forward on Purpose.

This humanity-first approach is what I see as the future of work, the fourth option of cobbling together a career. That future is what some of the happiest people I know are doing. That reality isn’t applicable for everyone right this second though.

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Back to reality

We all know you shouldn’t put all your eggs in one basket, but practicing that wisdom is challenging while you’re living life.

One thing I stress to clients is diversification. My husband and I have six income streams. We didn't start off this way - it took us 10 years to get here. His corporate salary is our largest, but if it disappeared tomorrow, we wouldn’t be left with nothing.

Here’s one more thing I learned the hard way: once you figure out your ideal, it won't remain that way forever. It will evolve alongside you.

The only constant in life is change.

What doesn’t change is who you are and why you are here. Stay curious about both. Learning how to adapt and flow with the current is what will keep you steady. 🌊

Remember, Monica?

If you also find yourself shooting down all of your ideas, then I have something for you.

I will teach you the exact career transition strategy I use with my clients. For free.

🎣 The catch? You'll hear about my other offerings for 3 minutes towards the end. So this workshop is best for people who are curious about working with me, but want to "try on" first (with no obligation to buy).

I'll launch this workshop if enough people show interest. Reply to this email with the word "workshop" and I'll let you know if it launches.

Take care of yourself,