^{Shameful Plug}

Want to know your options?

I’ve met and spoken with a dozen users in the past week at Habits.

Whether you want a financial advisor or not, the beautiful part about our marketplace is figuring out your options. Answering questions like…

• At what age does it make sense to work with a financial advisor?

• What if I just want a quick, TL;DR review of my finances?

• Where do I rank amongst my peer group(s)?

• What does a financial advisor cost?

So I’ll keep it simple:
→ Download the app 
→ Or book a quick call

^{Main Story:}

The 3 Most Embarrassing Moments of My Career (That Taught Me Everything)

There’s this weird paradox that happens when you start taking big swings in life: the higher the risk, the higher the cringe potential. I've had some wins, but I’ve also had some brutal L’s. The kind you want to bury deep down and pretend never happened.

But f**k that. These three moments humbled me, shaped me, and whether I like it or not got me here.

1. The Day I Nearly Got Fired

Six months into my first (and only) corporate job, I was already circling the drain.

I was working on an intense team with high turnover, the kind where analysts lasted months, not years. One banker in particular had made my life hell. For example, he once printed out a Word doc titled “10 Things Jack Keeps Screwing Up”, bolded every item, and made me tape it to my desk in front of everyone.

And still, I couldn’t get it together. One night I took a shortcut on a pitch deck by copying typical disclosures from another client’s presentation. Something every analyst does, but this time, I didn’t double-check. And that client? A direct competitor of the one we were pitching.

The next morning around 4:30am, I got the call. “What did you do?” And I recognized it was this bankers voice, but I was so groggy he just replied “Check your email.” Needless to say, I panicked and sprinted to the office.

Every managing director got pulled into the war room that day. Both parties involved in this conflict that I had created needed to be notified. We lost the deal. And I sat at my desk white as a ghost, knowing exactly what I had done and how bad it was.

Later that day, the banker took me to a private lounge, poured me the stiffest whiskey I’ve ever had, looked me dead in the eye and said: “Get your sh*t together and figure it out.” Then he walked out.

I stayed. Not just that day but finished the rest of the analyst program. Became the longest-standing analyst that team ever had. Not because I was perfect, but because I learned how to survive, take ownership, and show up even when I wanted to disappear.

Takeaway: Hustle means nothing if you’re careless. Triple-check your work and own your screw-ups. And if you want to hear this story in further detail check out the TikTok below.

@jack_boudreau_

Replying to @Justin just a good ole conference room breakdown #wallstreet #banking #nyc #investmentbanking #wealthmanagement #assetmanagem... See more

2. The Job I Turned Down (and the Man Who Tore Me Apart)

Years later, I was bootstrapping Habits in Boston. Broke, exhausted, but slowly building momentum. That’s when I got an offer that made me question everything.

COO-level role at a company doing $150M+ in revenue. Massive salary. Travel perks. Reporting directly to the CEO of the parent company. A career-maker — the kind of job that would punch my ticket to private equity, VC, you name it.

But I couldn’t commit. When I finally walked into the office to talk it through, the person offering the job (someone who had fought hard to get me in the room) absolutely unloaded on me.

Questions like “How much have you raised? How much revenue do you have?”
How ready is your product? How many people are on your team? …..”

Every answer was some version of: I don’t know yet. I’m figuring it out.

And then he said the line that still echoes in my head: “This startup is going to bankrupt your relationships, your career, and your bank account.”

He walked out of the room and never spoke to me again. Never responded to a single text. Gone.

I was gutted. Not just because I lost the opportunity but because I saw, for a second, how crazy this leap really was. I didn’t have all the answers. I barely had a decent idea of when my next paycheck would come. But for some reason, I still believed in what we were building.

So I muttered the same words that banker drove into me years earlier: “Figure it out.”

Takeaway: Sometimes you just have to make peace with the fact your gut feelings are right, even when they sound wrong out loud.

3. The Founder Dinner From Hell

One rainy night in Boston, a banker friend invited me to what I thought was a casual networking dinner. I figured 50 people, open bar, name tags, small talk. Easy.

Nope.

Full floor of a luxury restaurant. Total of 20 guests. Two guys footing what had to be a $50K bill. And everyone else in the room? Titans. Family office founders. Biotech CEOs. Franchise moguls. People who casually mentioned their third home.

I had gone full-time on Habits six weeks prior. No customers. No revenue. No employees. And I was the first to introduce myself.

I fumbled through a two-minute word salad trying to explain what we did. My banker buddy finally cut me off: “Jack, since we’ve got a lot of people — how many customers, how much revenue, and how big is your team?”

All were zero.

The next 19 intros were basically Shark Tank meets the Forbes list. And I just sat there, wet from the rain, wildly underdressed, feeling like an absolute loser. Anxiety through the roof. Imposter syndrome off the charts.

But that dinner (as brutal as it was) taught me how to read a room. How to own where I am without overcompensating. And how to fine comfort while uncomfortable.

Takeaway: Confidence isn’t pretending to have it all figured out. It’s showing up anyway.

Final Word

Embarrassment blows. But it’s the universal reminder and teacher. It doesn’t feel like it in the moment. It feels like failure, shame, humiliation. But every one of these moments pushed me to get sharper, tougher, more self-aware.

I used to be scared of being the guy who wasn’t ready. Now I realize the only way to become ready…is to keep showing up, even when you feel like a fraud.

So if you’re in the middle of your own career mess? You’re not alone. And it’s probably not the end. It might just be the beginning.

Feedback for Jack

Enjoyed this newsletter? Forward it to a friend and have them signup. Alternatively, use the referral link at the bottom of this email.

What’s Coming Next?

It’s hard for me to come up with a title to describe it, but I’ve always been a believer that a founder’s job is to maximize your ability to get lucky. So I plan to dive into the tactics and philosophy behind it!

Sharing Is Caring

Do me a favor, if you enjoy this, share it with a friend!