Your flexible W-2 Is actually a trap

Flexible hours. Remote work. Good salary. An MBA program his employer was paying for.

On paper, it looked like he had it all. The security of a paycheck plus the freedom to build his real estate business on the side.

But when I asked how many deals he’d closed in 16 months, the answer was zero.

His comfortable job wasn’t giving him the best of both worlds.
It was giving him an excuse to never fully commit to either.

Research on entrepreneurship shows that fear of failure has a big negative effect on entrepreneurial behavior.

Translation: the more you worry about failing, the less stuff you do.

And here’s what makes that flexible W-2 so dangerous - it doesn’t feel like fear.
It feels smart. Practical. Responsible.

You tell yourself you’re being strategic. Building slowly. Testing the waters.

But psychologically, you’re hedging. And hedging prevents the mental shift required for entrepreneurship.

Studies on risk aversion show we weigh potential losses twice as heavily as potential gains.

So that comfortable job isn’t just income. It’s psychological insurance against the pain of failing.

So you never pick up the phone. You never ask for the money. You never take the leap that demands that you open up your sails and go for it.

Because you don’t have to.

The comfortable trap works because it’s invisible.

You’re not screwing around doing nothing.
You’re learning. You’re networking. You’re analyzing deals.

But you’re not closing them.

Because closing deals requires something your safety net won’t let you access - Vulnerability.
That desperate urgency that motivates you.
The willingness to look foolish while you figure it out.

When you have a flexible W-2, you can always wait……
for the perfect deal, until you know more, until you’re really really ready.

Except you never get ready by waiting.

Here’s the first move. Say the hard truth out loud. Name it to tame it.

“I’m keeping this job because I’m scared to go all-in on real estate.”

Not because I’m being strategic.
Not because it’s flexible.
Because i’m scared.

Research shows that naming your fear reduces its power. When you call it what it is, you stop letting it control you unconsciously.

So say it. To yourself. To your spouse. To a coach.

“I’m scared to let go of this safety net.”

Now you can actually work with it.

Stop telling yourself you’re building a real estate business.

You’re building the skill of handling discomfort.

Every time you pick up the phone scared, you’re practicing courage.
Every time you ask for money when it feels awkward, you’re learning to do hard things.
Every time you introduce yourself to somebody new, you’re solidifying your new identity.

Reframe it:
“I’m building the skill to ask hard questions.”
“I’m practicing being uncomfortable.”
“I’m finding out what I’m made of.”

When you focus on skill-building instead of outcome-chasing, the safety net matters less.

You think keeping your W-2 protects you from loss.
But what are you actually losing by hedging?

Time.

The flexible job you worked so hard to get is costing you years of building what you truly want.

Momentum.

Every month you don’t go all in is another month your competitors do.

Your Superpower.

You can’t become an entrepreneur by dabbling. You become one by committing fully and figuring it out.

The comfortable trap isn’t protecting you.
It’s stealing from you.

That syndicator will probably keep his flexible job for another year. Maybe two.

He’ll keep telling himself he’s building slowly. Being smart. Playing it safe.

But one day he’ll look up and realize the gap between where he is and where he wanted to be is massive.

And the safety net that felt so smart was actually the thing holding him back.

You can’t hedge your way to freedom, so be brave.

To going all in,

Chris

Cacciotti, G., Hayton, J. C., Mitchell, J. R., & Giazitzoglu, A. (2016). A reconceptualization of fear of failure in entrepreneurship. Journal of Business Venturing, 31(3), 302–325.
Kahneman, D., & Tversky, A. (1979). Prospect theory: An analysis of decision under risk. Econometrica, 47(2), 263–291.
Kong, F., Zhao, L., & Tsai, C. H. (2020). The relationship between entrepreneurial intention and action: The effects of fear of failure and role model. Frontiers in Psychology, 10, 229.