Entrepreneurs: Show Us Your Secrets

stories & musings
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Title graphic for Hillary Wiess blog post titled Entrepreneurs: show us your secrets.

I spent last weekend at the glorious second annual Failure Ball, put on by the legendary Jess Manuszak herself.

It was a fabulous evening, full of fun, flop stories, great food, and everyone’s finest eleganza (and I was honored to co-host as the Resident Extrovert. You can catch my lil’ outfit reveal here, and a mini recap of the weekend here).

It was also, almost unexpectedly, a spoonful of sugar added to the medicine I so sorely needed.

Because on the stage that night, toast after toast to failure shared a common theme:

What happens when you take the gloves off and go for it?

On the Other Side of Failure

From owning a diagnosis.
To embracing an art form you didn’t expect to love, even if it doesn’t turn a profit right away.
To enduring financial (and personal) betrayal from friends and business partners.
To spending three years writing a book that was eventually scrapped — because the writer had spent so much time diluting her voice out of fear of “being professional”.
And so much more…

… Across the board, at the other side of these stories lay self-discovery, satisfaction, better boundaries, and one serious banger of a final book.

But that wasn’t necessarily what set off the lightbulb for me.

Instead, it was a chit chat by the bar with a lovely lady with sharp eyes and beautiful silver hair named Constant who, under the twinkling chandeliers, shared a question that had changed her life.

A “former special ed kid” (her words) turned educator, turned consultant helping teachers better manage a range of learning styles in their classrooms, Constant felt pretty clear she was living her truth.

Then, a speaking coach asked her this question at a training session, after unceremoniously panning a buttoned-up talk she’d debuted:

“What is it you don’t want us to see?”

Oof. Ouch. What a thing to ask.

And, while it’s not my place to tell you what Constant was trying to keep from view, once that truth was revealed?

Once she took the gloves off, let the veil fall, and spoke not only from her truth but also allowed those attributes she wished to hide to come to the surface?

She received a thunderous applause, and a standing ovation.

And it changed her life, and the way she taught and shared, forever.

I have no doubt she’s changed lives in room after room she’s been in after that, too.

The question itself blew through me like a missile, and forced myself to ask the same one.

What is it I don’t want YOU (yep, meaning YOU, Dear Reader) to see?

If you’ve been around a while, you may know by now I’ve grown out of using this email list as my personal confessional over the years.

There’s a Reason Boundaries Aren’t Transparent

First, because I’m a boundaries girl, and second, because as the success of my business has grown from $23k in my first year, to 6 figures, and now solidly in the multi 6-figure range for the last three years, so has the potential for risk (in my mind, anyway).

And for a little while now, I’ve wondered if my writing has suffered for it.

Not that I necessarily owe anybody details of my private world, or that anybody is even particularly interested.

But transparency has always been a value of mine. It keeps me grounded, honest, and awake.

While I haven’t necessarily been hiding anything on purpose, I find that the brighter one shines (my joyful choice, I might add!), the more difficult it can become to point to one’s shadow — because, frankly, you wonder if people want to know.

After all, the brightness drew them in. No one stays on the dancefloor after the disco ball shuts off. In fact, it’s an indicator that the night is over, and you need to leave.

Which I think is why that particular question Constant shared felt like a light switch being flipped on in a room that’s been dark for years.

And why the stories at the Failure Ball meant so much to me.

Something Big is in the Works…

Because, in a lot of ways, I’m about to go for it with my work in a way I haven’t before.

And, while I still don’t feel the need to trot out every wound, scar, and skeleton for your assessment in the interim, when we keep the gloves on and try to only shed light on our Best Selves all the time, we can never truly emerge in our bigness and greatness.

And so…

For the first time in a few years…

… Let me tell you what I don’t want you to see.

Not because I think my baggage is wildly interesting, or I need to show you my wounds to prove I’m a person, actually.

But because as I step into this next chapter, it’s gonna require me to show up in full force. Which means shadow’s gotta come along, too.

Let Me Lay it Out For You

Here goes:

First, I don’t want you to see the fact that I have a “good girl” problem — especially in business.

In my day-to-day life, it means I let Bad Stuff go on too long.

I’m almost always one of the Last Friends Standing in a multi-human-falling-out saga, no matter what kind of hits I’ve taken in the process. And, by the time I actually do exit stage left, my attempt at steadfastness has usually caused more problems than it’s solved.

In the business world, that means I’m deeply reverent and deferential to my teachers and mentors, to the point of reinforcing my own smallness — sometimes to the vocal confusion of those around me.

(Can I tell you how embarrassing it is to be called out on that by friends and colleagues!? Because WHEW.)

Over and over, I’ve contorted myself into stylish little knots, and deliberately making financial and strategic choices to avoid stepping on anyone’s toes, or upsetting them.

Unfortunately, almost every time, the Bad Stuff I’m trying to avoid with this delicate dance (jealousy, resentment, and abandonment, mostly) happens anyway. Everyone’s charming as a supporting character. But once you step into your own spotlight, you can become a threat.

So at this stage in my life, I’m working on rethinking the above.

How Far Can You Go Betting on Yourself?

Because, while I don’t intend on turning into a massive jerk, my need to try to anticipate and accommodate others’ emotion invariably blows up in my face and stifles my own growth and happiness.

I have no idea what that’s gonna look like, as I’ve been this way my whole life. So wish me luck.

Second, I don’t want you to see that, if you ask me to say the words: “I’m in a league of my own with what I do, and aim to create more incredible, out-of-the-box brands for clients and myself with my talent” out loud, I might actually throw up on you, and myself.

I know, I know. This is literally what I help other people do all day every day — and man, am I good at it.

But you know what they say: we become the medicine we most need for ourselves, too.

To quote my colleagues — I have an annoyingly good knack for knowing what sells, shaping full-suite positioning strategy, developing messaging, and crafting visual direction (both photo and video).

It’s not even that I hate talking myself up. I’ve got a healthy ego, and I’ve got a lot of hard-earned love for myself.

But, because of the aforementioned “good girl problem” when it comes to owning my range of skills, and the things I could create if I really let ‘er rip… historically I will absolutely choke on my tongue if you were to ask me how far I think I could go.

Now, I think that era is coming to an end in a big way. Because I want to see what happens when I bet on what my brain can really do.

So stand by for more on that.

And the Last Confession…

Finally, I don’t want you to see that for me, embracing personal style isn’t just a form of ultimate self-expression. It’s also a weapon and a shield.

It’s a blessing to be born with Big Energy… but sometimes it can also feel absolutely monstrous.

When you’re told over and over as a kid by family, authority figures, and friends to tone it down, you’re too much, and you’re better in small doses, you find a million little ways to lock yourself down and avoid sucking all the air out of the room.

And, in an Internet Land of constantly-trending “Why are people so people, amiright introverts?????” content, it’s seen as gauche to find joy in attention, loudness, and brightness.

In that sense, fully embracing bold, occasionally-outrageous style has set me free.

It gives me a reason to stand out without saying a word, to invite conversation without pushing it on others, and to project my personal expression and response to my environment into the world around me like laser beams.

Sometimes, I treat my style like my superhero costume. Who do I want to be today? How do I want to be seen? What do I want to give myself permission to do?

At other times, it’s a shield. A way to disguise my internal world, or protect it from the outside. I can dial the subtlety spectrum up or down depending on what or who I want to repel, or attract.

And at other times still, it can be like a weapon that cuts through the still air, projects the confidence I want to feel, and announces to the world: YOU MAY NOT WANT ME, BUT DAMNIT I’M HERE TOO, BISH!

Dress as Your Superpower

So when I dress myself, as well as my clients for photoshoots, it’s not just a matter of what they like, and what looks good. I also consider: “How can this be a weapon or shield for them, too?”

And so there it is. The things I’d rather you didn’t see, now out in the light of day to catch a little tan.

As oddly uncomfortable as these are for me to share publicly, I’m realizing more and more that owning each of these items loudly and proudly might just be the key to exactly where I want to go.

And frankly?

Here’s to that.

Here’s to you, and to me.

And here’s to the things we stash away in the shadows — praying they’re never found because we’re embarrassed, ashamed, or frustrated that we’re STILL rotating on the hamster wheel of our own patterns after all this time… when they’re likely the very things that will unlock entire worlds for us.

I certainly aim to find out.

Wish me luck.

Thanks for being here with me,

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