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Why “Living the Dream” is Not for Everybody

I have friends who will email me from time to time with amusing messages like “dude I wish I could surf all day and write blog posts like you do.”  I’m always amused by how little work they think goes into everything that I do.

Over the last several weeks I’ve realized that living the dream is not for everybody. Some people just don’t have the stomach to stand on the edge of success with adversity as the catalyst. They get so caught up in looking at the lives of other people they tend to lose site of the difference between what they think we want and what they actually want. So, how do you know whether or not living the dream is for you.

7 Signs That Living The Dream is Not for You

Instant Gratification

If you’re the kind of person who has a need for instant gratification you will  be severely disappointed by the amount of work it takes to live the way I live. Building any sort of online empire is probably one of the most thankless journeys you’ll ever experience in your entire life. You have to work at every single day and often it will feel like there is no light at the end of the tunnel. If you can’t let go of the need for visible progress, then you’ll probably feel like pulling your hair out.  It takes a while before you see the fruits of your labor.  But, ultimately the payoff is worth anything you have to go through.

The Need for Certainty

If you need to to wake up every single day knowing exactly what’s going to happen, then living the dream is not for you.  You’re continually living on an unpaved road, and hoping to find the beauty at its end. There are going to be moments when you don’t know how much money you’ll make next week or next month. Sometimes it’s more than you expect, other times it’s not. You have to live your life accordingly  and be willing to deal with the sporadic nature of life as an entrepreneur.


Given that living the dream is filled with days that test your patience and build your character, if you’re not patient, then this not the life for you. Take a look back at my first two weeks of life as a digital nomad and you’ll see just how much of a pain in the ass it can be to live the dream sometimes. Getting the point where you really have everything you want takes experimentation and time. You’ll have to live in dumps, kill cockroaches, and essentially deal with a few bumps in the road. If you need everything to be perfect and work exactly as you expect it to, you’ll be in for a rude awakening.

Attachment to Your Possessions

A while I go I sat down and made a list of just how much useless crap I own. Fortunately over the last year I’ve made a point to acquire as little as possible. As a result I can now move in and out of an apartment in about 15 minutes. But some people are attached to their things. If you need fancy cars, every pair of shoes on the planet, and a bunch of other crap that can really weigh you down when you’re traveling, then you really need to consider whether or not living the dream is for you. You might be better off on a two week vacation, staying in a nice hotel. There’s nothing wrong with that at all and plenty of people do it. Hell it’s probably much more convenient than living the dream.

Looking Good on Paper

When I finished business school, I realized that my whole life had been about the ego driven pursuit of a life that looks good on paper.  I wanted to have a Bain. Mckinsey, or some other big brand name on my resume because so many of my friends did. I suppose to some degree that’s also a byproduct of growing up in a culture of expectations. It’s likely if I setup a dating profile on an Indian dating web site and wrote “I live in Costa Rica and I surf everyday”, I probably wouldn’t be the most eligible bachelor on the site.  The thing is that my life will never look impressive on a resume.  But considering a resume won’t even get you your dream job, I don’t really care.  If you’re life is about nothing more than filling up a list of paper with accolades then you definitely are not cut out for living the dream.

No Self Motivation

As ironic as it might sound for somebody who is a complete beach bum, what I do takes a hell of a lot of self motivation. I have to write without anybody telling me to. I have to reach out to potential guests for BlogcastFM without anybody telling me to. I have to get work done for clients and even look for new ones without anybody telling me to. Nobody is going to tell you what to do and if you need that then living the dream is not for you.

A Need for Structure

If you haven’t noticed by now, living the dream is an unstructured way to live. It’s different every single day. There’s no set schedule. There’s no set amount of work to do  and there’s nobody telling you when it needs to get done.  While there are components of it that are routine, there’s really no set schedule. You work your own hours and work doesn’t necessarily end or begin at a certain time each day.

So, before you set out on a mission to escape the grind, give conventional wisdom the finger, sell everything you own and leave the country in less than a month, give some serious thought to whether or not you really have what it takes to live like this.  It’s not for everybody.

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