Dear Overachiever: What If You Didn’t Have to Wait 10 More Years?

Don’t wait a decade to feel alive.

I never thought I’d work for myself — and then I did.

Five years ago, I was still working full-time as an engineering leader.
By day, I led big teams and high-stakes projects.
By night and weekend, I coached — quietly, passionately, on the side.

Coaching gave me meaning.
Tech gave me money.

I told myself I’d keep doing both for eight more years.
Stack the savings.
Hit financial freedom.
Then, I could retire from tech and finally do what I loved.

But the universe had other plans.

I got laid off in the middle of the pandemic.
I could’ve gone back to tech — the job market was still hot.

But I couldn’t motivate myself to work for another ego-driven exec.
Even though I know there are great white male allies out there… they’re just rare.

I debated what to do next.

By then, I’d been coaching for nearly three years.
People paid me. Lives changed.
But I still didn’t see myself as a “real” business owner.
Until one day, my coach asked:

“What would you actually do once you’re financially free?”

I said:
✨ Coach more.
✨ Be with my family.
✨ Work from anywhere.
✨ Choose who I work with — and when.

Then it hit me:
What if I could create that life now — instead of 8–10 years from now?

That moment gave me the clarity I needed to go ALL IN.
It was terrifying.
But it was right.

Now, four years into coaching full-time, I’m still so grateful I said yes to myself.

Because I’m not waiting anymore.
✨ I’m living the life I used to save for “someday.”

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How about you?
What life are you waiting to create?
And what if it doesn’t have to wait?

Loving you,
Wen

P.S. If you’re at a crossroads — wondering what’s next or feeling the pull toward something more meaningful — you don’t have to figure it out alone.

✨ If you want a thought partner who gets it, let's talk: https://calendly.com/wencoaching/strategy