The math, magic and madness of investing in YOURSELF.

As a former financial advisor turned entrepreneur, I often spend my days justifying my ludicrous decision to walk away from certainty in favour of a blank slate. I mean, it was such an all-or-nothing move.

But also on brand, if you ask anyone who knows me. I’ve never been great at being part pregnant, half present or just a little bit tipsy. If I’m going to do something, it needs to be ALL THE WAY. Reminds me of this video I love.

Besides—it was impossible to attempt any movement towards my dream so long as I was in the role of taking care of my clients’ financial well-being. And that’s fair. They deserved my time and attention. The regulators saw it that way, and I did, too.

I’m here to say that taking such a big risk on myself has been the craziest roller-coaster of my life: an exhilarating, puke-inducing, clutch those handle-bars, and strap-yourself-in ride. And I’m not complaining, I’m just keeping it real.

My logic when I made the leap:

  • I’d taken a risk in love and that seemed to pan out! My brazen (read: drunken) saunter-over at my friend’s wedding paid off and Mr. Rebound and I are still together 25 years later. 
  • Surely I’d learned some things about risk, reward, what I loved, hated and how I wanted to serve in the world after 16 years in an industry that kept me running on a treadmill.
  • I was on the verge of cracking anyways. Might as well crack at something I truly love, no?

That all checks out. Plus, I’d have the mentorship of my dad, one of the greatest business dudes I knew. (Note to my father: I sure do miss you and all of our dad/daughter chats. I know you’re with me in spirit.)

Recently, though, I’ve had to take stock of what it means to go ALL-IN on your dream. That’s financially, emotionally, in your body, and for the people around you who wipe those tears when you feel like shelving the whole damn thing.

Investing in Something Uncertain

Don’t we do this anyway?

We save in our retirement funds. We entrust our advisors to make good recommendations. Hell, we do it ourselves and try to pick stocks that will pay the most lucrative dividends in the long run! This is not a super fun thing to do. But it’s a societally-acceptable method of salting away nuts for the days when we’re not as quick on the gathering.

And yet.

As I transferred over one more loan into my little baby start-up, that stabbing pain I sometimes feel when nervous almost knocked me over. I’d never seen the account so low. This account is supposed to be for WHEN WE’RE OLD. And newsflash? We aren’t getting any younger!

It’s supposed to ensure that we aren’t living on stale Saltines and squatting in a van, down by the river (not that there’s anything wrong with that, in fact, it sounds like a little slice of heaven right about now).

I mean, what business do I have continuing to pour money into my business?! How long does this entrepreneurial reinvention take? Come on, UNIVERSE!

All these questions stem from my own naturally-occurring fear. Because, guess what: I’ve been trained to mitigate risk at all costs. And, I’m no dummy. There are no guarantees on our dreams. P-SHAW! How many businesses start and then fail? I’m not the only one to have gone ALL-IN on some vision.

The Math of Investing in Yourself

But here’s some nifty math… Take away the money I’ve invested, crunch some future financial scenarios minus that money and the outcome in the long run is not that big a deal. I was floored!

On the other hand, let’s say that She Walks the Walk becomes the thing I imagine it could become, or that this next round of investment helps it grow to a new level—then that’s not for naught, right?! My illuminating moment came when I realized that I was investing in something I believed in, something I put effort into, something I saw a need for, and something over which I had a degree of control.

The Magic of Investing in Yourself

Since launching SWTW in the fall of 2020, the journey has not been a straight line. At times I feel like I’m living in a real-life sim of Snakes & Ladders: two steps up, slide backward diagonally, jump forward unexpectedly, go back one, and so forth. Life has dished out an endless slew of curveballs—pandemic, regulatory BS, the loss of my hero, earthquakes and wars, to name a few—but I’m still here.

Still trying. Moving forward. Learning. Growing. Analyzing. Getting real. And each time I wonder what my next move is, someone impactful, or something unexpectedly positive comes my way. This can’t be coincidence.

The people who’ve shown up with possibilities and opportunities to help SWTW (and, me) are nothing short of magic.

Take Kristin… She came into my world all because I left my AirPods on a plane, and she happened to hear me lamenting about it to a front-desk hotel employee in Tanzania. End result? She and I are now partnering on my future Kilimanjaro offerings. That I’d meet someone with such shared values, offering the perfect partnership package for my clients? It just doesn’t happen like this.

Or, take the chance to compete in a Speaking final when I’d not officially earned my way in… That just doesn’t happen. But randomly, on a Wild Card opportunity, it did. And I’m so grateful! I’ve always believed SWTW should have a speaking sleeve—a platform to help get my message out there to other women. This is one more shred of proof that the universe can AND WILL co-create with us if we get out of our own way.

The Madness of It All

My whole dream of helping women off the treadmill could be one massive delusion that results in a fantastic mid-life Belly Flop… possibly at the expense of a so-called retirement. Possibly at the expense of my sanity (see the initial paragraph about my ALL-OR-NOTHINGness).

But when I hear stories of other women like me… women who are at the point of near-cracking, trying to balance it all, give it their all, hustling and pushing and never ever stopping for one goddamn second— well, I want to SCREAM!

This is my WHY. Why I try. Why I put up with the Snakes & Ladders game that has become my new business life. Why I stop myself from walking into a bank or a financial institution and selling my way into a leadership position. Something I know I could do in a heartbeat. But that I know would be out of integrity with who I’ve become over these last few years.

If You’re Out There TRYING

Making something from nothing is not for the faint at heart. It’s why most people just don’t do it. The safer, easier path is the one we are trained to tread. Off-roading at this stage in the game feels like a one way ticket to Crazy-Town. (And be assured, it is! But I’d rather this straight jacket than my trusty old RRSP season blazer ANY DAY!)

So. If you’re like me and you’re out there working on your dream, working on a midlife reinvention, fear not. You aren’t alone. And I want to remind you of a few guiding principles that keep me grounded when the fear threatens to shut everything down:

  1. Success is not measured only by numbers. Look at how far you’ve progressed!
  2. Having no regrets counts for something. We will ALL DIE anyways. Might as well die trying.
  3. Your children are watching you model hard work and possibility for them.
  4. Entrepreneurship is magic and madness. You can’t have the magic without a little crazy.
  5. Pursuing the most authentic expression of how you’ll serve in the world matters.
  6. Things take time. Please remind of this, like, tomorrow. ‘kay?

If you have a reinvention story to share, I’d love to hear it. Or, maybe you’re a woman on the treadmill wondering how to stop yourself from flying off the back-end. I want to hear from you, too! We haven’t been put on this Earth to simply toil away in isolation.

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