This may come as a shock…

(3-ish minute read)

This may come as a shock, especially to those who know me well, so sit down and buckle up.

I’m a “talker”.

I know, I know, a truly brave admission.

Gift of gab, extreme extrovert, social butterfly, *cough* loud, obnoxious, center of attention *cough* – there is no shortage of adjectives that have been used to describe me. In my defense, I could talk before I could walk (seriously, ask my Mom) so it’s not like this is a new development.

Recently, however, I’ve tried to be more conscious of that.

I try and ask more questions than I’m asked. I try and listen more than I speak (gulp). I try to be present and interested during conversations I’m not particularly excited to be in. Try being the operative word.

“God gave you 2 ears and 1 mouth, so listen twice as much as you speak.” Yeah, yeah, yeah, thanks, Mom.

I know I’m not great at it, but I’m trying because I notice when other people aren’t great at it and, frankly, it drives me nuts.

Like, what is behind me that you keep looking over my shoulder? Why are you texting in the middle of our conversation? Stop saying “right, right, uh huh, okay” after everything I say.

Wait, I’m not like that…am I? 

Anyway, the last few months I’ve had a lot more free time on my hands and I’ve been spending quite a bit of time networking.

A very common question I’m asked when meeting new people is, “So what’s your story?”

Simple enough, right?

Wrong. I mean, how much time do you have? Where should I start? Middle school? High school? College? Post-college? Shit, I’m only 28, how do guys twice my age answer this question without needing a nap in between?

As a form of practice, when I ‘tell my story’ I typically try to give an aggressively Sparknoted version, which still requires an Ace Ventura Inhale.

“Started an odd job company in middle school, did it every summer through college, blew all my money first semester, wanted to bring WAK Jobs to colleges but was too busy (lazy) so, instead, had a few friends start seedling versions all over the country. Graduated and started working for a startup in NYC…***…jumped on a one-way plane ticket to SF, got convinced to do WAK Jobs full time, one-way ticket back to Boston, started GladlyDo the next day. Took out a loan, grew the business for a year, raised some money, grew the business for another year, started pivoting to the B2B space, went to raise my second round of funding, met a Venture group in Philly, negotiated for 6 months and eventually sold them the business. Moved to Philly, relaunched as Laborocity, grew it to a multi-million dollar business, went to raise money but ultimately was bought out by our investors, took some time off to travel a bit, visit family, and now looking for something new and exciting.”

*Ace Ventura Exhale*

As I use this blog to wind through the finer details of those ‘chapters’, I feel it’s important I fill in as much color as I can, even if it’s a shade darker.

Well, hidden in that “***” above is a little known but wildly important part of my story that I leave out 98% of the time I tell it.

It’s one of the few things I don’t talk about, at least not publicly, but I’m starting to think maybe something I should because…

*Pulls out soapbox*

…we live in an Instagram glorified culture these days where you only see the “best” picture, the trophy, the achievement, but I think that misses the bigger picture.

I miss the old days, where someone would put up a Facebook album after a night out and you’d anxiously scroll through to see if you had a new default pic, but more importantly, which pictures needed a swift de-tag. That damn double chin!

No photoshop, no filters, no “influencers” in a bikini posting how FitTea changed their life.

The closest thing we had to ‘airbrushing’ was using Paint to color over beer cans or blur out the background so your parents didn’t know whose house you were at. (Mom, if you’re reading this, do NOT check the Halloween picture in my high school yearbook!)

My point isn’t to bash social media (I’m scrolling Instagram drinking FitTea as we speak 💁‍♀️) and it’s certainly not a ‘hot take’ to claim that we glorify everything online – I just wish we could peek behind the curtain more.

To me, it’s about the lows. It’s about the hardship and the struggle and the tireless effort. I’d rather listen to someone talk about the ten times they screwed up over the hundred times they succeeded any day of the week.

I just find it more genuine, more relatable, and frankly, more helpful.

So, with that in mind, I will do my best to be brutally honest throughout my story whether there is a lesson to be learned or not.

It happened, so here it is.

With that in mind, I can say without one ounce of exaggeration that the one pivotal moment I eluded to earlier changed the course of my career, and likely my entire life.

It was the day everything seemingly ended for me. But, five years of hindsight later, I can now say it was the day my life truly began.

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Previously, on WAK Job…No Regrets

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