Not long ago, I put up a poll on LinkedIn asking people why they stay put in jobs they no longer love. Almost half said it was because of financial risk. When you still have a job, corporate seems stable, even with all the layoffs. When being a full-time employee is all you’ve known, doing literally anything else seems reckless.
Now, if you’re living paycheck to paycheck, that risk is real. And this episode is not for you.
But if you have savings you’re afraid to touch, a lump of severance cash just sitting in your account, or if you’ve already spent money on workshops and seminars to figure out what’s next, keep listening.
We’re going to look directly at financial risk and how to calculate what you’re actually dealing with.
The risk is real
Even with money stashed away, you still have obligations. Healthcare, kids’ college, your own retirement funds, your rent or mortgage. You want to know that none of that will be threatened.
But the real risk is staying too long and getting ejected without a plan. If you’re working at a big company, you might feel like you’re swabbing the decks of the Titanic. You see Amazon lay off 30,000 people in four months, and you know your company could be next.
Removing layers and restructuring is built into this corporate capitalist system, even if the posters on the walls espouse very nice-sounding values. So it’s time to look at the system clearly and make a plan before they force you out and cause you to scramble.
The Distraction Economy
Can I tell you how many courses I purchased and never completed? Several. It’s so easy to spend money on things that feel safe. A weekend retreat that feels great but changes nothing. All the books.
So you’re already spending money on the idea of clarity. The question is whether you’re spending it to figure out what you want, or to avoid building it.
Face your Fears
Some of your financial fears are real. Some aren’t. You need to know which is which.
You’ll have to get a handle on three numbers: what you spend every month, what healthcare will cost, and how long your cash will last. The first one is in your bank statements. The second one is on healthcare.gov. The third one is division. All of it could make you queasy. Do it anyway.
Pull up your credit card statements and checking account direct payments from the last six months. Add them up and divide by six. That’s what you actually spend, not what you think you spend.
In the US, healthcare will cost you somewhere between $750 and $1500/month, depending on your state, coverage, and whether you have kids. If you’ve had corporate benefits for years, this number will make you want to crawl back to your desk at work. Look it up anyway. Know the cost of COBRA if you’re eligible. Factor in your out-of-pocket expenses as well.
The last number you need is the sum of all your cash reserves in bank accounts and brokerage accounts. Once you have that, you can determine your runway.
Your runway = liquid assets / monthly spending.
Your discoveries will inform what happens next.
Cue the Negotiations
Here’s what might happen when you run the numbers. You discover you have 8 months of runway. Maybe 12. That should feel like relief, but instead you panic harder.
Because now you don’t have the excuse anymore. The math says you could do this, which means the only thing stopping you is you.
So you start negotiating with yourself. “I should wait until the kids are done with school.” “I need to save three more months, just in case.” “The market is too uncertain right now.”
These might be legitimate concerns. Or they might be ways to avoid admitting you’re terrified.
I’m not going to tell you which one is true for you. But I will say this: if you keep moving the goalposts on when you’ll be ready, you’re probably not actually waiting for more money. You’re waiting for the fear to go away.
It won’t. You build the thing while afraid.
Risk Requires Runway
Some paths need more time and capital than others.
A short runway and in-demand skills might lead you to consulting or fractional roles.
If you have a longer runway and specific ideas for a business, you can start planning for that. Or you can take a few months to deprogram from the corporate world.
And if you have a decent amount of capital on hand, you might look into purchasing an existing business.
Experiment starting now
For those of you still in corporate jobs and planning for life after, now is the perfect time to start small experiments. You have a steady paycheck and health benefits. Only by trying things and getting feedback will you know what actually works.
A client proposed monthly lunches with former colleagues from two different companies. She had no agenda and no plan. But being in regular contact made her the first candidate for a consulting role with one of the colleagues. She hadn’t even thought about consulting until people started asking.
Another client started sharing designs from a side project he’d been working on for a year in secret. That turned into an offer to package and sell the idea – something he didn’t think was in the cards.
These experiments don’t require money. They require your time and energy. The feedback you get – from yourself and from others – will tell you what to drop and what to keep pursuing.
The Real Calculation
If you’re anything like me, scarcity is a familiar state of anxiety. You worry that there won’t be enough, that you don’t deserve to invest in the next thing because you aren’t pulling in income immediately. That you have to stop getting coffee from your favorite coffee shop.
What’s actually true is that starting to build something new while you’re still employed gives you a safe lab for experimentation.
Some people decide they’ll only quit once they’re so busy with outside activities and moonlighting gigs that they don’t have time for their day jobs anymore.
Others get unexpectedly laid off and pour themselves into the plan.
Both strategies require planning and clarity. But they don’t require confidence – you gain that as you go.
What’s next
Whether you’re currently employed or not, what’s one experiment you could start this month? It doesn’t have to be the million-dollar idea. It just has to tell you something you don’t know yet.
Burn the map. Build what fits.
>Curious about the path that might fit you best? Check out the recent series “The Reluctant Entrepreneur”
