Confessions of a 26 Year Old Entrepreneur : Under30CEO Confessions of a 26 Year Old Entrepreneur : Under30CEO
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Confessions of a 26 Year Old Entrepreneur

| November 14, 2012 | 14 Comments

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 Under30CEO. After two years traveling and working from his laptop, Matt's official title became Adventurer in Residence, heading up Under30Media's travel company Under30Experiences. If Matt is around he will be easy to spot as his long luxurious hair is generally flowing freely in the breeze.

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  • Dina Eisenberg

    Matt, I loved your journal entry. So honest and helpful.

    Like you, I built a ‘portable business’ that let me fulfill my lifelong dream of moving from the frigid East Coast to balmy northern California.
    It’s been an amazing experience to have this big adventure, but it’s also been stressful.

    I’ve had to rethink every aspect of my life and business. Brought up a lot of doubt but also gave me a wonderful opportunity to ‘do over’ things in my business that I didn’t love.

    Living your dream is a process, not an end game. Diamond sparkle more when polished. Thanks for reminding me how luck I am.

  • MattWilsontv

    Hey Dina, I’m really glad you enjoyed my honesty. It’s not easy showing the world when you doubt yourself, and I was a bit nervous about it.

    The best part about this whole adventure has been the learning experience. People think if you make a big change in your life like moving to paradise, your whole life will automatically be simply that– paradise. I completely agree it’s about trying to constantly refine your dreams and figure out how to improve the quality of the journey.

    Thanks Dina, we both truly are lucky.

  • Fernando Guzmán Cárdenas


    I read your full confession since I’m 26 also.

    Before I continue, about me: I have an excellence degree in Humanistic Psychology, I’m also studying a Master Degree in Humanistic Psychotherapy, while also studying another degree in Administration. I’m also a full-time worker. I have a girlfriend, and I will be a father in January since we are pregnant, plus, I also do exercise everyday and I’m the owner of a Coffee Shop. So many things for my age also… This is just to link an empathy with you, because I want to reply your confession as a comprehension of not what you just wrote, but of what YOU WANTED TO EXPRESS in the confession you wrote:

    This is my reply to you:

    It seems like your hard work and your constant desire to achieve things has given you a lot of nice things to yourself and the people around you, and some bad things, as you just said, your body is reacting about your constant behavior and is asking for a nice rest, like yelling: “HEY!! HERE I AM!!! STOP LOOKING AROUND, JUST LOOK INSIDE!” and you tend to reply that request as “I know!, stop!, I’ll do it!, I’m joining Yoga… but never mind, I better do it while I move to one point to other”

    Do you think that your body wants a “meanwhile” attention? of course not! it’s your body and you need full attention to it!. you got to find out the way you really are, and stop being the way other people expect from you, because that seems to be the case in many aspects of your life (resuming a quote you wrote: “attending others, attending your work, not attending yourself”)

    I like this blog, you work hard, and if one day there is no news, it may have an impact in every reader, but there is always a nice way to move on and maintain readers’s confidence, which also, you got to find that way by yourself. Nobody is perfect…

    But keep healthy, you are young. WE are young, and I’m sure that you, just like me, want to life a very long pleasing and healthy life.

    I’ll share a phrase that may mean something to you:

    “Stop achieving perfection, you won’t reach it, and start living your own imperfection by improving it”

    Fernando. (MX)

  • Chris Hughes

    dude absolutely true. As entrepreneurs we often get stuck on the “hustle” and making sure that our dreams work no matter what.

    Right now I’m sitting in Boquete, Panama and have luckily been getting out for a few hours each day to explore and hang out with friends. I’m getting a few super focused hours of work done in the morning after a workout and find that this is optimal for me in accomplishing goals.

    However a couple weeks ago I had a HUGE breakdown. My bank account got down super low and I had no idea if I should continue on with what I was doing.

    I guess the best advice I can give is to schedule time for all of those things that you first wanted to experience when you started your Entrepreneurial quest. Remember that you got into the biz so you could do the stuff you want.

  • MattWilsontv

    Hey Chris, great to hear from you. Hope you are enjoying Panama, I’m dying to check out Bocas del Toro. Let me know if you are going to be in Central America for long.

    Most of the things in my journal entry are written because I’m trying to balance my travel, business, and spending time with people I love around the holidays. It’s actually more of a stress for me this year to make crazy travel plans to see everyone because I haven’t been there. It’s also tougher to call home because of the time zone and that I can’t call from my cell phone. When I sit down to my computer I’m trying to get focused on my deliverables, and I’m not in “call a friend and chat mode”. Of course, I’m trying to make up for it when I get home.

    Anyway– love the notion that you should own your business instead of your business owning you. It really is why we started it in the first place. Cheers from Bali!

  • MattWilsontv

    Hey Fernando– I appreciate your thoughts here, and you are right– that is a lot of what I’m feeling. I think the post was relatable because every entrepreneur makes sacrifices and often does it at the cost of their own personal well being.

    I’m having an absolute blast out here, but having fun is not necessarily the same as taking care of yourself, and in a lot of cases (partying) (sleeping less to do more fun things) having fun can actually end up being detrimental.

    It really is true, that before you serve others, you have to serve yourself. Thanks for the note and good luck with everything this year, sounds like you’ll do well.

  • Garth

    Hey Matt, how about an article about the technology that holds your roadshow together, from your laptop to smartphone, to the wordpress/whatever CMS you use, tips and tricks to pull it all off. Also a bit of a background of the day to day operations, and perhaps your skillset. would be awesome…

  • Chris Hughes

    we’re going to be checking out Bocas del Toro later on this week as well as Boca Chica to compare to see which is better. I’ll probably be in Central America for another 2-3 weeks… it may be longer I’m not 100% sure. I have a flight back to Florida on the 27th, but I really am enjoying this life and how cheap everything is out of the states.

  • Garth

    No love for me :(

  • MattWilsontv

    cool man enjoy Bocas del Toro, drop me an email and let me know how it is! I hear it is paradise.

  • MattWilsontv

    Hey Garth, thanks for the suggestion. I’m pretty basic as far as iPhone and MacBook. Skype and Google Voice. iMessage and Whatsapp. Other than that I’m a minimalist, but maybe I’ll write a tech for the minimalist article :)

  • Garth

    That would be awesome, I guess what I and maybe other wonder about this kind of lifestyle, is how to make it profitable on a shoestring. Does the your entire income come from your websites, or are you running workshops etc, any other form of work ? is your day to day mostly blogging ? I know that it can be tough coming up with new content all the time ? and lastly, who handles the design side of things for your site ? or is it a CMS of sorts ? thanks for taking the time to answer :)

  • Pat Larsen

    Hi Matt. Great post. Very honest. So many people want to be in your shoes but they love the idea and no idea of the reality of it. I live in Chicago and was working in Japan and Taipei over Christmas/New Years for clients in the US while traveling/vacationing. I was jet lagged out of my mind anyway but it wore thin working from 9pm-4am each day.
    Making appointments with yourself helps. I use the index card method. Making your plans physical (on paper that is portable) is way better for me than anything electronic. I put meditation and exercise on there. Three 5-minute sessions of each, every day. 30 minutes total but it makes a difference.
    Many entrep’s say that you have to take a day off every week. You have to make an appt with yourself to do nothing. There is a reason that major religions keep to this over thousands of years. It works. It keeps people sane. It keeps peasant populations from rising up in revolt because they’ve all gone crazy.
    The fact that you know things aren’t right is pretty important. At least you don’t have blinders on.
    Sounds like you are waiting for something really bad to happen to shake things out? I used to drive really, really fast and then I had a double roll over and then I chilled out a bit behind the wheel.
    Maybe you can hire a VA or two to do the admin/mechanical tasks that you don’t need to be doing. Even if you don’t want to, it’s great practice for delegation and growing your bandwidth.
    Best of luck on the journey.

  • Jason Baudendistel

    I totally know how this feels. I got literally physically sick and run down promoting my first book and last business. I almost sacrificed my health by not maintaining a healthy balance.