3 Things That Suck About Reinventing

Few people understood my desire to walk away from my first business when I was a known thought leader banking multiple sixes a year. 

By all accounts, I was a success. (Unless you compare me to my old colleague Bruce Krebs, who’s a franchise legend in my eyes. But we know better than to compare, don’t we?!)

If I had clung to that old version of success, I would’ve never created a sales training program that helped hundreds of service-based business owners sell their services. Or started my accelerator that’s equipped women to build sustainable businesses over the past 6 years. Or host a podcast that breaks through our self-imposed barriers to success.

Or, of course, having the time of my life being a thought partner for business owners as they navigate the angles of their own reinventions.

But reinvention isn’t only about being on the other side of it, sharing your glamorous success stories while guzzling bottles of Dom.

There are a handful of things that seriously suck about it.

And some people might not having the stomach for change due to three things that can make reinventing a bumpy ride…

#1 Veering away from the safety, security and comfort of something you know (or think) is already working for you.

I just GOT here!! Can’t I take a breather? Pleeeaaaaaase?

That’s right. You’ve got steady money coming in so you can’t walk away. Are you insane?!

Feeling bored, unchallenged, empty, unfulfilled — or downright hating it — can seem like pretty skimpy rationale when money’s at stake. 

Especially for people who lean on logic, but tend to ignore the tiny voice inside, just begging for more.

Plus money’s not the only thing you think you’re walking away from.
Don’t forget about the reputation you’ve built.
The assets and content you’ve created.
The relationships.
The knowledge.
The… welp… all the things.

Which leads to the next thing that sucks about reinvention. 

#2 Uncertainty about whether or not your next evolution will work.

What IS my next thing, anyway?

We entrepreneurs never have a shortage of ideas. But which one do you pursue? What if it bombs and in hindsight you realize you should’ve chased down that other idea? Or that other one?

Oh, how that feeling of not knowing sucks. Where’s the crystal ball, damn it?!

This waffling leads to an “indecision paralysis” situation:
Not putting a stake in the ground traps you in a state of indecision.
Indecision breeds inaction.
Inaction leaves you where you are, which is no bueno if you’re feeling itchy.

It probably comes as no surprise to you that I’m with philosopher Maimonides who said, “The risk of a wrong decision is preferable to the terror of indecision.”

Once you do decide on your next move, you’ll end up dealing with the third pain in the ass aspect of a reinvention…

#3 Explaining to others why you’re changing lanes. Again. 

When I started my first business back in 2002, nobody understood why I’d leave Oracle because of sucky reason #1 above.

I was earning free President Club trips to Hawaii. 3-hour shopping trips to the Oval Room with my personal shopper over lunch. A fat, steady paycheck.

Explaining my shift to my peeps was harder than describing micro-economics to a first grader.

But damn, I gave it my best.

And then, when I decided to leave my first business to start my second, it was even more shocking to my friends, family and colleagues. I’d built that baby up from scratch. I was a known thought leader, speaker, author, expo founder… 

The explaining started all over again.

And then I finally learned to say, “I don’t expect you to understand. I don’t fully understand it either. But it’s just something I’ve gotta do.”

End of explanation.

Let’s face it, reinvention isn’t for everybody. 

Well, really it IS for everybody. But some people won’t do it anyway. They’ll choose comfort and predictability over growth.


In my universe, feelings of self-expression, freedom and contribution can’t be traded for the safety of continuing to do the same thing. In fact, that doesn’t feel safe at all! Give up personal and professional growth in lieu of living my days, stagnant and unhappy?


The great news is that you don’t have to give up all of the things you’ve done up to this point— because they factor into your new, reimagined business, in some way, shape or form. That doesn’t always mean it’s WHAT you’ll be doing. But it always plays a supporting role.

The fun is in the figuring out. 

One of my top 3 core values is Adventure.

Reinvention (in addition to flitting off to Cambodia with a week notice — or living in Barcelona for a month) contributes to a life of self-discovery and adventure.

If you know your core values, maybe you can save yourself the headache of attempting change if it doesn’t sync with any of your top 5 core values.

Ah, who am I kidding?

We’re MEANT to reinvent.

We’re designed to go BEYOND where we are today.

It’s going to happen whether you go looking for it or not. So brace yourself. And now that you know the sucks, you’ll be on guard when they roll your way.

Considering your own reinvention, but wary of the sucks? 

If you want to supercharge your reinvention to create your next big thing, use the calendar below to book a conversation with me. Over the course of 30 minutes, we’ll determine your readiness + resources to ensure you stick the landing!


Posted In: Thought Leadership