5 Minute Sunday · The newsletter for founders and leaders who are tired of being the bottleneck
"I just need a break." Most founders I talk to this time of year say the same thing.
No. You don't.
You need to find out if you're still on the right path. The vacation just happens to be the first quiet room you've had in months, and quiet rooms are where the real question finally gets to speak.
Here is how I run that conversation with the founders I work with, and why almost none of them want to have it.
🔑 ONE LEADERSHIP TIP : The reflection most founders wait too long to have.
When Tracy, a Series A founder, told me in June she was finally taking a real week off in August, I was worried about what she'd do with the silence… but also super excited she was finally doing it.
Most founders treat rest as a temp charging station. Charge the battery, get back in the field. That's not wrong. It's just incomplete. What almost nobody does on vacation is ask the one question that actually matters: is this still the direction I want to be running in?
They skip it because they're AFRAID of the answer. And to be honest i get it, i feel the same terrifying fear when i see somehtign is not working and the moment i stop moving and working i might discover- o sh* t i probably not heading the right way. once I started asking clients directly, the pattern was always the same three stages.
Stage 1: Separate two skills that get treated as one.
RESILIENCE is showing up on the hard days. Working 15-17 hours a day non stop, no weekends its nothing's glamorous. That's real, and most founders are good at it.
REDIRECTION is stopping to ask if you should still be running in this direction at all. Almost nobody trains this one. They think if they're resilient enough, they never have to.
They're wrong. Resilience without redirection is just momentum with good PR.
Stage 2: Give a Name to what's actually being avoided.
Underneath it is the label. Change direction as a founder and somewhere in your head it reads as FAILURE, not as data.
I have spent a month in New York, and founders there wear a failed startup like a credential. Two that didn't work is proof they're still trying. In Europe, that same sentence gets said quietly, if at all. Even me, when i feel like something is not working im ashamed to admit it and make it look prettier than it actually is : o they choose another direction.. No they choose NOT ME. I've come to see that as a cultural inheritance, one that says nothing about whether stopping was the right call.
Dan, a senior engineer I mentor who tried and failed to raise for his own startup, wouldn't bring it up for months. When he finally did, he said it felt like admitting something Shameful. He coudnt even tell his girlfriend about not able to raise the money. What he'd actually learned was the most useful thing he picked up all year: you didnt fail, you learned, and next time , you will make things differently. He realized that after 2 sessions with me and finally said that aloud, he needs to pivot and try again.
Stage 3: Give the question somewhere to land.
This only works with real disconnection. Not answering slack, your kids or talking to Claude. one to two hours, while things are actually quieter this month and most are on vacation, hopefully you as well.
Write, unedited, answers to four questions:
→ Am I actually happy, most days, doing this?
→ Is there something in my work I genuinely enjoy, or does it just feel like a roller coaster I'm strapped into?
→ Am I seeing real results, or am I waiting for a deadline to tell me it worked?
→ If I'm honest, do I need to change something?
Whatever comes up, don't call it failure. Call it discovery.
If the answer is leave, leave, and be proud you tried. If the answer is stay, stay, and go back with your eyes open instead of your head down.
Tracy told me after her week away that the hardest part wasn't the questions. It was believing she was allowed to ask them without it meaning something was already broken in her and her startup.
That's the shift.
🏢 ONE COMPANY WORTH KNOWING :
Slingshot AI, and one founder who did this on purpose.
Slingshot AI is the team behind Ash, an AI mental health app trained specifically on clinical and therapeutic data instead of general internet text. They've 93million dollars to build what they call a foundation model for psychology.
The technology is the headline. The founder story is the real fit for this week.
It was cofounded by Neil Parikh, who had already built Casper into a household mattress brand, alongside Daniel Cahn, a machine learning researcher who'd previously built AI mental health tools in the UK. Parikh has said that being back in the founder seat, building from the ground up again, is both daunting and exciting.
He wasn't stuck for a direction. He'd already succeeded once. He chose to face the unknown again anyway, in a completely different category, at the exact point where most people with one exit behind them stop.
The bonus case study, for anyone who thinks "very late" and "still made it" don't belong in the same sentence: Colonel Harland Sanders. Before Kentucky Fried Chicken, his twenties and thirties were a string of failed jobs and businesses. A short legal career that ended in a courtroom fight with his own client. A ferry boat startup at thirty that a new bridge made irrelevant. He was 65 and living on a small Social Security check when he finally incorporated KFC and started driving around the country signing up franchisees himself.
His whole life was a string of pivots, one after another, until one of them finally worked.and boy we all know how big this chicken worked.
✅ ONE THING TO ACT ON This week:
take the one-two hours.
Block one to two hours while things are quieter. Phone off. No calls, no internet, no exceptions.
Write, unedited, your honest answers to the four questions above.
Then ask yourself one more:
If I decide to leave, or decide to stay, who is the one person I trust enough to say it out loud to first?
You dont have to carrying it alone, because you been bold, you took a risk and you are doing something you need to be proud of !
Do this before the summer's quiet turns back into crazniness..You get one run at this.
Don't wait until it's too late to ask.
📩 TWO WAYS I CAN HELP
If you want the exact four questions and the reflection framework I use with clients: Comment REFLECT on LinkedIn and I'll send it to you.
If you already know something needs to change and you want help figuring out what:
We'll talk through where you actually are right now.
See you next Sunday
— Alisa
Leadify | Fractional COO · Executive Advisor
Founders come to me when they've become the ceiling.
This issue also ran on LinkedIn — join the discussion there
