Tips for the Entrepreneur and a Successful Vacation

It’s vacation season!  

Three Vacation Tips for Entrepreneurs

Tickets are booked, shopping is done, and bags are packed! So much planning and prep has gone into this- the only thing left to do is have fun, make memories, and reconnect with loved ones. 

You finally get to your destination and everything is accounted for. Except for your partner’s head; it’s back at the office- again. 

For most entrepreneurial couples, this is a common point of contention. 

“Just once! We just wanted your undivided attention for just one week!”

Trouble in paradise. 

Below are a few helpful tips to ensure everyone maximizes the power of family vacation:


‘Trep: Honey, I have three business calls I need to take while we’re away. They’re scheduled at these times…

Partner: Babe, there are a few times this week we’ll need your undivided attention for scheduled activities. Can you please make sure you’ve planned accordingly to have your phone off during these times?


‘Trep: avoid the impulse to defend taking a call with “you never appreciate how much I have to work to make all this possible”.

Partner: avoid using this as another opportunity to prove that the business is clearly more important than family.

Let it be what it is. A call. After the call, a kind gesture from each of you will unhinge the other from the impending battle positions you may have both assumed. 


‘Trep: is it really necessary that you engage in work while away? Or do you just enjoy being needed/engaged/ challenged? A total disconnect provides exponential value in your business and your personal life. Don’t underestimate the power of letting your team handle it- everyone will thank you. 

Partner: is it totally crucial that no work activity takes place? Or do you just feel a little lost when they they get caught up in work? Taking advantage of some personal time while on vacay gives you an equal opportunity for a total disconnect- and what’s that worth?!??

I hope these simple but game-changing tips help you have the best vacation yet!



705 Million Vacation Days Wasted Last Year!


That’s the number of VACATION DAYS WASTED last year.

Today is National Plan for Vacation Day and here’s why that matters.

💰The travel industry is BOOMING right now so last minute inventory is hard to come by. You’ll pay a premium if you don’t plan in advance

🎁 Life finds plenty of opportunities to spring unexpected stress on us. But very, very rarely do surprise vacations pop up. It’s crucial to be mindful about putting the good stuff in our lives.

🌅 PLAY is actually a prerequisite for success. The more time we spend enjoying our time away from work, the more productive we are at work AND it gives our VIP’s (family) the sense that they are our priority.

⏰ When do you want to use your vacation time? Now, while you enjoy good health an active lifestyle, and growing relationships? Or after retirement, when health and abilities are declining and social/family circles begin shrinking?

Entrepreneurship: Finding your bliss

When was the last time you were shibumied?

“Shibumi” my dad said out of nowhere. 

We were on a family trip to Costa Rica. It was our first family trip that my brother and I were allowed to bring S/Os so our family of four was growing to six. 

We’re sitting outside on the patio at the resort drinking cocktails under ambient lights with the waves in the background, listening to live music and enjoying first night of vacay vibe with our growing fam. 

Out of nowhere my dad goes “shibumi” and I could tell he was in bliss. I asked what that was? He said “that moment when everything is perfect and there nothing else in the world you need or want, but there’s no word that really describes it.” As a parent, it must have felt like an awesome point of arrival to be traveling with adult kids and their partners. I got it.

Feeling bliss

I know that feeling well. Travel always bring it out in me. So does theater. And tender moments with my kids. 

It’s in those moments that we’re brought to our knees in gratitude that we actually get to experience a piece of heaven on earth. It’s the swell of joyful tears and the clog of awe in our throats. That’s shibumi. 

The best thing about shibumi is that the more you experience it, the more there is to experience. Just like love (and anything really) the more you have, the more you get. 

Schedule time for bliss

There’s ironic quality to shibumi. You have to proactively schedule time for it to show up. You have to actively put the elements into your life that create shibumi. It doesn’t guarantee you’ll achieve it, but its the only way it becomes a possibility. 

Shibumi doesn’t happen in the grind. It happens in flow. It doesn’t happen in the hustle. It happens in the pause. It doesn’t happen in work. It happens in play. 

It’s why play takes such a high priority in my life. Because it’s where shibumi shows up for me. And shibumi is the fountainhead of everything else in my life. 

My book came out of shibumi. My work came out of shibumi. My kids came out of shibumi.

It’s that important. 

Yes, “play” is cute and silly. But if you don’t put the good stuff in, it’s harder for the good stuff to show up. 

When was the last time you were shibumied?