Confessions of a 26 Year Old Entrepreneur

by / ⠀Personal Branding Startup Advice / November 14, 2012

Editor’s introduction: The following is a freehand journal entry by Under30Media Co-founder Matt Wilson.  Matt has been working location independent since this summer and wanted to share with you his view of the world through the eyes of an entrepreneur living and working his ass off from paradise…

here i am sitting in bali.  absolutely in paradise.  working and living from the most serene place in the world.  completely run down.  i’m emotionally drained.  i’m tired. i’m weak. i’m off pace.  i have no balance.

i’m killing it

bali.  yoga. surfing. living the dream

thanksgiving. family. home. friends. fall.

birthday party nyc.

costa rica 12 days.

back to the office.  we’re killing it.  top revenue month ever.  2 new sites.

montreal. new girlfriend. gotta learn french. meet the parents.

key west. christmas. time to chill.  spend time with my family.

i’m killing it.  but it’s wayy too much.

but something has to give.  i can’t go on like this. i’m burning out from paradise.

these words make me vulnerable.  i pride myself on my strength.  i give everything i do 110%.  if i write this, what will they think?

“keep the wheels on tight” they told me.  “move back to the city and be realistic” they told me.

if i show vulnerability, will this all have to end?  as an entrepreneur, as a man, is it okay to show the world that you doubt yourself?

–wow, someone just served me fresh strawberry juice by the pool.  i’m am killing it

Honestly, I don’t doubt myself.  An an entrepreneur I have an incredible life.  It was built this way by design.  But why am I burning out?  I’ve seen 6 countries in the last 3 months, I have amazing friends and family, and I’m fortunate enough to have a business partner who is somewhat understanding about my crazy scheme to work / live abroad.  I want to prove that I can do it.  We can win.  And most of all I hate when people doubt me.

Giving 110% to my business means sacrificing.  I’m not sightseeing everyday. Sadly, I’m not surfing everyday, and even more sad, I’m in Ubud, Bali’s yoga capital, and I’ve only done yoga once.  My work hours from 7AM until 3PM and then 7PM until 1AM are wearing on me, but hell, I’m seeing the world, I’m in paradise, and I’m going to play with elephants and monkeys this weekend.

Okay, emo kid… how bad can we possibly feel for you.  Get to the point.  What can I learn out of this?

Getting out of your comfort zone can be insanely difficult.  I’m halfway across the world right now.  Earlier this month, we owed someone more money than we’d ever had in our bank account in our life.  When you are building a business, you often get that feeling in the pit of your stomach that makes you want to hurl.  That’s when things get interesting.

Without risk, there is no reward… and without the journey, what’s the point of the reward?

Reflect. Relax. Rethink. Recharge.

Every entrepreneur has had this point.  Their brain is fried.  They are trying to do too much.  As a friend who I confided in about this sent me this morning:

“When things stop adding up, start subtracting.”

… as another brilliant entrepreneur friend told me yesterday.  There are only three things that matter when it comes down to your most valuable asset: time.

  • Time with the people you love.
  • Time to work your ass off.
  • Time for yourself.

…oops.  I guess I forgot time for myself.   

Every entrepreneur is guilty of it.

When I’m done working, I’m traveling.  It might seem like “time for myself” but I move every 5 days.  I’m not taking time to recharge.  My diet is sh*t.  My workouts are next to non-existent, and I haven’t read a book in weeks.  As I tweeted the other day: “I feel like I’m trying to squeeze every last drop out of life.  But is that the point?”

Most importantly, if I would have simply reflected everyday, I wouldn’t have to go so far as to rethink.

I’m not going to fail.  I’m not going to give up.  The most ironic thing is that for a Type A entrepreneur, the most beneficial thing I can do right now for my business is to relax.  Even from paradise, it’s possible to over-schedule yourself both personally and professionally.  Here’s to the simple life…

Matt Wilson is Adventurer in Residence at the travel company Under30Experiences.  Join them on their next adventure.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.