The "Is self-employment a good fit?" framework continued...
Catch-up links below.

When you’ve worked in corporate jobs for a while, you find there’s a good amount stability to enjoy!

You’re working with the same team every day, towards an established mission, and of course, you receive a steady salary and benefits.

That’s not to say curveballs don’t happen (hello, layoffs!), but aside from major disruptions, you can look ahead to the next 3-6 months with a decent expectation of what’s in store.

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When you go out on your own, the freedoms you unlock come at the expense of some of that stability.

• Some months’ revenue will be high, and some might be zero.
• Your pipeline may ebb and flow.
• You’ll deal with a string of rejections.
• Your service portfolio will evolve over time.

In short, there’s change all around you, which can be both exhilarating and paralyzing.

The most effective soloists can meet that ever-present change not with capricious decision-making or panic, but rather with what I call ‘dynamic stoicism’:

• The ability to adapt regularly to a changing context...
• To embrace serenity in response to adversity...
• To maintain clarity amidst uncertainty...
• To prioritize long-term objectives over short-term wins

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The question to consider here is: can you handle the rollercoaster?

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This is tough to gauge ahead of time, but let’s look for evidence by considering the following:

Professional/corporate behaviors:

• Have you gravitated toward large, “safe” employers, or are you attracted to early-stage companies and nascent industries?
• How have you responded to major re-orgs or shakeups at your employer? Have they been energizing or demoralizing for you?
• When passed up for a promotion or a lateral move, how difficult was it for you to rebound and plan your next step?
• How have you handled rejections during a job search? Have you been able to see past the initial sting and jump back in to find the better fit.

Personal behaviors:

• Are there examples in your personal life where you’ve accepted that there’s no “right” way? E.g. parenting, or perhaps spiritual work
• Are there examples in your life where you’ve worked towards a goal in small increments over a long period (one or more years) — e.g. saving for a down payment, athletic training, securing immigration status
• How well do you deal with rejection in dating or other social situations?
• How have you reacted to sudden external shocks? — e.g. structural impacts of the pandemic, partner losing their employment, illness or passing of a loved one.

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This is a deep one — we’re a resilient species with an incredible ability to adapt to our surroundings.

But I encourage you to be brutally honest with yourself here — you likely can handle the rollercoaster of self-employment.

Do you want to?

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Next up: The final angle — the one everyone thinks about, but the one we dance around the most. (Hint: $$$)

💡

-Wes