Do Entrepreneurs Take Vacations?

Newsletter · Aug 03, 2025

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An entrepreneur's recipe for sweet success

3.5min Read

You might not like this answer, but it’s the truth…

We do, but at the same time we don’t.

So, no.

But let me explain. It’ll make total sense in a second.

I say “no” because the mind of an entrepreneur doesn’t ever stop. There will ALWAYS be something to do. Something to start. Something to build. Something to create.

Even when things are running smoothly, there will still be a shiny object or milestone you might be chasing.

That’s the nature of the game. I LOVE it. And I know you do as well. But we still need to be able to get out of town and enjoy ourselves with family.

While I am not out of the w2 grind (yet) and I have to juggle the cop job AND the entrepreneur in the trenches life, I still need to intentional about shutting it down and relaxing.

Maybe the mind won’t ever fully settle, but I have to try.

And if you’re anything like me, you struggle with this as well. I’m constantly asking myself “how can I chill when I’m not where I want to be yet”

But the reality is, if I don’t stop and enjoy the moments that I have RIGHT now with my family and if I’m too focused on the success-- I’m going to completely miss the “good ol days”.

So this particular email is dedicated to that. The following is what / how I delegate so that while I’m out of town, I can actually be out of town.

FIRST —
I’m writing this email here a week in advance. I know I’m going out of town and don’t want to have to worry or think about writing/ posting anything. I love to write. That’s not the issue. But it takes time. Time I much rather spend with my fam.

I’m writing this now, then I’ll send it to my executive assistant (she’s a rockstar) and she’ll tee up the newsletter for me to make the final edits and post. I’ll do all this before I go.

SECOND —
Every business is different. I don’t know what you have or do, but the specifics in this case don’t matter. Most are solopreneurs so I’m talking to you on this point.

Make a list of EVERYTHING you do during a normal week.
What things have to be done on a certain day
What things are extremely urgent
What things do you know ahead of time

Write it all down to see it. This is going to help in the future for sure when you actually delegate, but right now it’s you just having a visual of what you do.

Again, it’s all industry specific, but what's important is having a visual of everything you normally do. It packages your tasks nicely. From there it’s about prioritizing what you can get done, what you have to get done and what can wait.

I know that’s not solving your problems, but I promise you that seeing your tasks listed out brings so much clarity.

THIRD —
You’ve gotta delegate. If you’re leaving in a week, maybe this isn’t the time to hire… it’s not, seriously. BUT if you just want to start this process of creating a little more freedom on your life, do this

hire an executive assistant. Do it for ONE task. Maybe keep them part time if you need to, but have them do ONE thing for you.
As they learn and master that one thing, start recording Looms of you doing other things. Send those Looms to them and have them study your process until they feel comfortable with tackling it.
Accept the fact that it won’t be perfect at first, but it’ll get pretty close eventually. Give it time.

FOURTH —
Here’s the kicker. Read this one over a couple of times if you have to…

It’s not all going to get figured out. There will always be problems. There will always be people that need your time and try to pull you away from vacation mode with your family. That is a FOR SURE thing in life.

You only have so many opportunities to go on these vacations with your family, enjoy them! Let this stuff get figured out later. Or as much of it as you can without blowing up the ship… but if you do, I guarantee that you’ll figure it out in the end.

So — I have all these things in place. I have my EA. I have a back office and call center. I have business partners and AI automations. BUT there will still be things that pull me away. I’ll have to fight it like the rest of you and focus on what’s important. Not easy, but doable.

BITES

Bite 1 — How to find inspiration

Bite 2 — Rabbit Holes of learning

Bite 3 — Mysterypreneur Link

Bite 4 — AI Juice 🧃

BITE 1 — How to find inspiration
… and further, how to take that inspiration and make something out of it:

I don’t want to launch into a whole long monologue on this. It’s not that complicated. We MAKE it complicated by thinking that it is. It’s not.

What it requires more than anything is just iteration.

Posting and sharing day after day and slowly but surely figuring out what works and most importantly, what doesn’t.

Inspiration isn’t a magical unicorn to chase, inspiration is EVERYWHERE as long as you are looking.

My mission is to provide as much value as I can, detailing the blueprint of my entrepreneur journey. And to do that, I am constantly looking for lessons, tips, tricks and hacks in everything I do so that I can turn it around to something worth sharing.

My journey might be unique to me in many ways. But the principles still apply and my hope is that even one person here can take something away from all these wild ventures I talk about.

I debate all the time whether I need to JUST talk about my vibecoding or JUST talk about the home service businesses or JUST about being a dad-preneur... but the truth is that all of those things together are what makes me, me. And all the things YOU do--make you, you.

If you are on your own journey and want to “build in public” as they say, the best way to do that is WAY simpler than you’d think.

You literally just need to do the thing you want to do and pay attention to the things that are difficult or that you’re struggling through.

Get through them and then share what you’ve learned.

Maybe you’re not even through it yet. That’s ok--Just share what you’re doing.

Someone might need that specific post as inspiration to start their thing.

“One day you will tell your story of how you overcame what you went through and it will be someone else’s survival guide.” --Brene Brown

BITE 2 — Rabbit Holes of learning

I’ll make this short and sweet for you—Be curious more.

Chase shiny objects.

Read more than one book at the same time.

Listen to podcasts while you run, walk, drive, etc.

Don’t worry about overconsumption, worry about not learning something that interests you.

If something piques your interest, ask more questions. Immediately buy the book on it. Find videos about it and do whatever it takes to soak it up.

It might not be now, it might not be next week, it might not even be next year, but EVENTUALLY, all the learning you’re stacking will come together in a beautiful symphony of success.

Take the red pill and got down the rabbit holes. It’ll be worth it.

BITE 3
— Mysterypreneur Link

BITE 4
— AI Juice 🧃
We are living in a time when something like this is possible for anyone.

@thepatwalls

I made a million from my "silly little website project" 😀

10:0 AM • Nov 30, 2022 ↗

Until next time...

Stay in the fight,

My best tweet this week:

@kevinasrx

How’s this for a side hustle??

Bubble parties—

Minimum $250/hr

2-4 gigs a day x 7 days a week

Can run it with 1 person

When they’re not doing parties, they’re in “performing” at schools for “Bubble Science”.

Very low overhead

Quick math:

$3,500 - $7,000 / week

12:52 PM • Jul 26, 2025 ↗

My favorite tweet this week:

@alex_borkin

Non-Entrepreneurs are such a crazy bunch of people.

Yesterday I shared a story about us having communication issues with subcontractors.

Amazing subcontractors that do incredible work. Give us preferred pricing and have helped us build a group of successful businesses.

Yea

https://twitter.com/alex_borkin/status/1947387952033894881

Alex Borkin

@alex_borkin

The biggest challenge that I cannot figure out how to solve is this:

We have multiple in field employees and sub-contractors.

They do not care to use our team slack channel. Nor will they log in to update a CRM.

So often questions or updates about a project will be

11:53 AM • Jul 22, 2025 ↗