Image for post
Image for post

How I Built a Six-Figure Coaching Business and Treated Our Entire Family to a Tuscany Trip

I don’t talk about myself a lot. Because honestly, when I ask myself…

Why am I doing this?

Why am I building a million-dollar coaching business?

Why am I taking that risk?

Why am I stretching the boundaries of my comfort zone to areas I never knew existed — and doing things like marketing & selling — things that, in my former life as an academic, I never imagined I’d be doing?

When these questions pop up, I like to ask myself three other questions:

1) If not this, what?

Well. I could go back to teaching. Researching. But I’ve done that. And I chose to leave that world for very specific reasons. I’ve moved on and going back would mean moving down.

2) If not now, when?

Never. It’s now or never.

2) If not me, who?

No one. No one else has the unique set of skills — and the unique passion — for helping tech managers upgrade their careers.

So if I don’t do this, who will?

THAT’S what drives me. YOU!

I know you need help getting unstuck from Career Hell.

I know you need help so you don’t end up settling for mediocre.

I know you need help so that you don’t burn yourselves out working 50+ hours weeks.

And I’m NOT going to leave you hangin’! I WILL NOT do that.

That’s why I don’t talk about myself a lot. Because it’s not about me. It’s about YOU.


If parts of my story will HELP you, then I’ll share.

Last year, in July 2018, I treated my family to a wonderful vacation to Tuscany. I paid for their airfare, our villa (in Lucignano), and several other outings/experiences including a catered picnic on the grounds of a monastery and a private tour through the Chianti wine region.

(Wine tastings included. If they wanted to buy a case or two, that was on them.) 🍷🌞🍷

We had a fabulous time and we’re going to do it again.

How was I able to do this?

I said I would.


Oh, you want more details?

Okay, well it all started about 6 years ago when I told my family I would treat them to a trip to Tuscany.

I told them, “Consider it done. We’re going.”

My family: “Okay Jen, that’s nice.”

And then a few years later, in 2016, I told them again, this time with a date attached, “We’re going to Tuscany in July 2018. And I’m paying for it.”

My family: “Okay Jen, that’s great.”

And then a year after that, in 2017, I told them again, this time with a location attached, “I rented a villa in Lucignano for July 2018. This is happening.”

My family: “Oh, wow. Okay. Where’s Lucignano? When exactly are we going? Do I need to learn to speak Italian? When are you buying plane tickets? How long is the plane ride?…”


In between all of this, I was building a six-figure business. And one of my goals was to earn enough with the business so that I could pay for this trip I said I was gonna pay for.

And I made it happen.

It wasn’t some magical, manifest-y thing where I repeated over and over, “The money for Tuscany will come. The money for Tuscany will come.”

Now, I do have my mantras.

“I intentionally choose to think, feel, and believe wonderful, powerful, beautiful thoughts of money, wealth, and abundance.”

That keeps me energized. Showing up at the highest level.

And then I show up. I do the work. I take inspired, intelligent action.

What does this all mean for you?

You have dreams. Some involve your career. Some involve the rest of your life.

How do you reach them?

You declare that they’re already achieved. You tell people, “It’s done.”

And then you do 2 things:

Show up.

Do the work.

Simple. But not easy.

That’s where we come in.

At The People Stack, we know how to help you show up your best every single day so you can become the tech leader you know you’re capable of being.

And we have the systems and strategies that will help you do the work and upgrade your career intelligently. And in an inspired way.

So you don’t keep running on the Career Treadmill…using up lots of energy but not getting anywhere.

We’ll help you get off that treadmill and run, skip, and jump towards your dreams.

Want to learn more about how we can help you upgrade your tech career? Check out our webinar today at

We look forward to chatting with you soon and helping you walk that path towards your dream career and dream LIFE — whether that includes visions of Tuscany or not.


Written by

Career Coach for Tech Managers. I help tech managers upgrade their careers, their teams, their paychecks, and their lives.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store