Vacationing as an entrepreneur

Every year since I was born, my family and I took great pride in the 7 day stretch of time off we took together. We would spend months, going over everything we would do, not do, things we WOULDN’T do, things we’ve done, you get it.

Every story got longer as it got told. Every detail would lavish on and on and the whole thing becomes very romantic as us kids got older and married.

Something happened when my sister and I came of age and took on management roles within our respective companies. Early morning breakfast, mid day drinks, late night beach walks were now punctuated with conference calls, emails, frustrations and yelling. There would be breaks with the family but generally you were either on the phone, the computer or asleep.

This behavior was always met with grief from our parents who always taught us to work our faces off, but now it was taboo. What I learned was, Hustle was life but you were expected to turn that off when family was present. It was disrespectful and unwise to show your work life. As if we kept two sets of books or something.

I speak 15 times a year to young groups of kids looking to start a life in business. They always ask me what I do on vacation. Surely the good life means fast cars, big mansions, fancy drinks and late night parties?! Right…?!

Listen. I’m just one POV here. But in all of my 15 years in business, I’ve never seen anyone that works for a living, live that way sustainably. It works in music videos and Instagram selfies but it’s not sustainable. We have a lot of fun, but being an entrepreneur is a life choice not a lifestyle.

This is what a day on vacation sounds like to a person obsessed with their life.

4:30am — early morning workout. Run, swim, bike, walk, move aggressively for 90 minutes. Get oxygen into your brain and feed it.

6:00am- meditation and reading. I read obsessively when I’m on vacation. I get bored without an objective and I’m most at peace when I’m learning something. Reflecting on what I want from the day is an objective. I write down 3 things I need to do and 3 things I want to do. Never skip this step. Big goals require care and feeding.

7:00am — caffeine and good food. I love eating and I’m useless without a cup or 4 of coffee. It puts me in a positive mood and that’s critical to the day of problems and team leadership.

7:30- email. Catch the team before work starts. Set the tone of the day, set objectives and respond to the results NOT the objections.

8:00am — family time, schedule sync, morning routines and news headlines.

8:45 — first round of management follow ups. Checking in on the team and answering customer requests.

From 9am to 11:30 I generally try to work on me. I’m on vacation with the ones I love and getting their feedback on life, love and happiness is critical to my mental state. This is the greatest time of my life and my family puts it all in perspective for me. We are so blessed to all be healthy and together that the moments seem fleeting if you don’t focus.

11:30–1pm- we eat lunch as a family. There are 9 of us and we’re Italian so this is extremely fun. It’s loud and delicious. Dad will make some sort of killer sandwich, the ladies will make drinks and the kids will typically nap. I try to catch up with my partner for a 5–10 minute call pending his schedule. We’re in growth mode and this is the midway point in the day. If something needs to happen for tomorrow, it can get fleshed out now.

1–3pm. Reading. On a week long trip I’ll close on 4 books depending their context. Real estate, money, AI, business or space. I don’t stray too far from those circles. Focusing on a topic all depends on what I’m working on. Right now we’re expanding so I’m devoted to real estate and automation.

3–6pm- my dad and I will cook dinner for the family and my mom and I will talk shop. She’s an insanely talented educator and highly motivating. She and my father are perfect parents and I spend as much time as I can learning from their kindness and generosity. They taught me about the human aspect of business and that Word is Bond. All lessons of integrity stem from them. They aren’t easily impressed but they are wildly supportive.

6–8pm dinner. Loud. Delicious. Chaos.

8–12am emails, phone calls, meetings with vendors. I write frequently and this is usually when. I’ll record a Podcast if that’s what I’m feeling, but I like to pass on what I’ve reflected on during the day as soon as possible to make it stick. Friends help tremendously with this process. They will offer their POV against mine, we’ll debate and make plans for my return. I’ll go through my list and make sure I moved the ball forward. I’ll typically try to turn in by midnight.

This is my vacation. It’s incredibly structured but no more so than a regular day at home. It keeps me on goal and never leaves me wanting. It’s what I’ve always wanted and returns year after year with measurable results. Sure, this opens me up for judgment but I’m completely free to my outcomes.

Warren Buffett said, if you HAVE to take a vacation from your job, never come back.

Meaning, if you’re a clock watcher, counting down the days until you can escape your lot in life, you’re doing it wrong. Find your work in yourself, not the other way around.


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