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3 Reasons Why You Should Stop Telling All Your Friends To Become An Entrepreneur




Entrepreneur Friends Shouldnt All So Business

Going back as far as high school, I lusted after the idea of doing my own thing. The problem was I had no clue how that would work our, or what I would do. I worked a tonne of odd jobs, and even the casual retail job from the age of 16 until I was 23. I joke about having a long resume of 2-month work stints, but it’s the truth.

Over time I learned that working a 9-to-5 simply wasn’t for me. As a result, I started my entrepreneurial journey.

I remember my last day at the call center job I had, and setting up a plan to succeed in my small university apartment on the first Saturday I had off in months. That was the beginning of what has been a very rewarding and challenging roller coaster ride. I always knew the decisions I made were the right ones, but something else, while not always super obvious, has been evident.

I am cut out for entrepreneurship because of various traits I possess.

I enjoy sales. I don’t mind a somewhat unstable income (at least when getting started). I like solving problems, and dealing with people. I have a deep appreciation for my personal freedom that comes from being able to determine my own schedule, and projects. I’m willing to live with less, and forgo some of the American ideals my peers are experiencing (having kids, buying cars and houses, etc) to make things work for me.

I’ve made these choices due to what makes sense to me as an individual.

I’m often asked how I got started, or what I did to get where I am, but once I begin to explain how, and what’s involved, some people are turned off.

In the past, I tried to talk my friends into starting a business, but I soon learned it’s mostly a waste of breath. But not because my advice wasn’t good, but simply because those people just aren’t cut out for this life.

And there’s nothing wrong with that. In fact, it’s perfectly normal.

I’ll be the first to admit it. Many entrepreneurs are crazy and many of us think our way is the ONLY way.

In reality, there are many paths to the same destination, but when you get from point A to point B in a manner that only makes sense to you, it seems like it’s the only way.

As a result, you might find yourself proselytizing to all your friends about how they should do it too, even if they have no interest or are scared stiff.

And that’s why I wrote this article — for all you go-getters who tell everyone to become an entrepreneur, you might ought to stick a sock in it.


1. Entrepreneurship Requires A Certain Personality Type

Many of us who enjoy this lifestyle are a bit eclectic. Some may even call us mad. I wouldn’t argue with them, and I’ll be first to admit to my fair share of manic episodes (just go read my Twitter stream). The up’s and down’s of this lifestyle are reserved for those who can handle it.

One month’s earnings can be amazing while the next month’s are next to nothing. If that phases you, I’d highly advise rethinking your decisions around working for yourself.

This life is about being a self-starter. I hate that title, but it’s the truth.

In my many job interviews, that was a key question –

“Would you consider yourself a self-starter?”

Every time I heard that I wanted to rip my eyeballs out and say “What do you think? I’m sitting here in a cheap pair of slacks, and a shirt my mom ironed in order to impress and convince you to give me 9 dollars per hour for making sandwiches and sweeping the floor.

A self-starter is someone who can figure out what they need to do, and begin doing it – at times without a fully developed plan. It’s someone who takes immediate action, and asks questions later.

If you’re not willing to work long hours (at least in the beginning), it’s probably not for you.

If you don’t get excited about the journey of reaching new heights, I wouldn’t sign up for this gig.


2. It’s Not As Easy As It Seems

Some of my friends would ask me about what I’m doing. When I’d explain my work day, and what’s involved, a very common remark is “your life is so easy! You’re lucky! I wish I could get paid to sit at home and run a website.

Now I will admit I’m lucky in the sense that I made certain decisions, and had certain people in my life who were instrumental in making those decisions, but none of this is easy.

In fact, I hate telling people what I do because it makes conversations awkward. I can’t relate to most people’s problems they have with coworkers, bosses, and rigours of waking up at 7 a.m. to catch the train.

On the outside, it seems glorious, but for those of us who’ve taken the plunge, it’s far from that life.

The mind of someone making their own way is a chaotic whirlwind at times. Everyone has their high’s and low’s but I imagine those of an entrepreneur are more pronounced.

Tim Ferriss said it best in his article “Productivity” Tricks for the Neurotic, Manic-Depressive, and Crazy (Like Me): “Most “superheroes” are nothing of the sort. They’re weird, neurotic creatures who do big things DESPITE lots of self-defeating habits and self-talk.”

But most everyone only sees is the outwardly productive and seemingly normal side of an entrepreneur.

They don’t see them dreading a project, or putting off client work due to fear of not doing it well enough. Or being burned out. Or dealing with depression and avoiding the therapist.

They don’t see them eating ice cream for breakfast and playing Grand Theft Auto: Vice City on his PS2 at 6am for 3 hours on the day a major project must be done

Talk about anxiety one can create for themselves through procrastination… but this is a normal part of life for most of us.

It’s a constant push/pull between extremes. One month, everything seems to be going great. You’re making money, sleeping well, and routinely socializing. The next month, you’re skimping on deadlines, moving your to-do list back a day, and wondering if it would be easier to go work at the Buckle… at least you don’t have to worry about setting your calendar, right?


3. It Won’t Make Sense To Everyone

We need people to work at the grocery store. We need people to work in factories that manufacture our eye glasses and clothes, and packages our food.

We need school teachers, and mechanics. We need librarians, and video game store clerks.

Not every single person can do their own thing. Plus, not everyone wants to. The demands of someone starting a business are much different from those who are working for the business.

Some people have a talent for management, organization, attaching soles to shoes. Some of them don’t wish to do anything else. So what?

Something I detest is trying to explain to someone who simply wants to work at their job why they should go out on their own.

Maybe they don’t care about doing something on their own… Maybe they actually like their job (newsflash: not everyone hates their jobs like I did). Maybe their profession allows them the money they need and the time to spend with their family.

They’re not us, and that’s okay.

Look on the bright side. While you may be enthusiastic about the decisions you made for yourself, many others might not be as interested. Save your energy and spend it on making yourself and business better.



Feature Image Photography by Fred Othero



  1. Avatar


    Jul 9, 2016 at 5:02 am

    Trying to persuade friends to become entrepreneurs is like persuading a loved one who doesn’t know how to swim to jump into the ocean. It will sound very wicked to them. Instead of wasting my precious time in persuading anyone to do their own thing, I rather encourage them to be good at what they do while I concentrate on my own madness’

  2. Avatar

    Sarah Como

    Jul 13, 2014 at 6:54 pm

    I totally relate to this article. I finally tried to stop convincing others to become entrepreneurs. However, I still struggle when it comes to my husband. He’s not comfortable with the uncertainty and does not have an entrepreneurial mindset. He encourages me to go for it but can’t relate.

  3. Avatar

    Nate Ginsburg

    Apr 29, 2014 at 1:36 pm

    Great article man! I’m gearing up for a trip back home and have been thinking about what it will be like to hang out with my old friends/crowd opposed to the SE Asia crew. I’ve also learned that it’s best not to preach.. You’re right, the life isn’t for everyone.

  4. Avatar


    Apr 16, 2014 at 6:36 pm

    Thank for you this amazing article. For the past few months of building my business, I ran into this wall and what you wrote describe exactly what I’ve been pondering about for the past few months, I realize I had learn so much from the pursuit of entrepreneurship and I see what it’s like out there for people who wants to settle for a job, I didn’t think it was fair for people to settle for a life of working for someone else, I cared so much about my friends I was trying to convince them that a job is not going to fill the dreams and goals you want to achieve. I had no’s and rejections and I took it personally because I had such strong belief that they would see what I see. After a few more months of growth and struggle, I definitely realize what I chose to do is not for anyone and that the friends I talked to wouldn’t even last a few weeks doing what I do, I became more aware of the things that an entrepreneur must go through that an employee will never experience in their lifetime.That is why only so few people choose this path, what an amazing insight indeed. Thank you so much JC.

  5. Avatar


    Apr 14, 2014 at 2:35 pm

    By the time I was in high school I knew that I will never, never work
    as an employee in my life. In my country, Benin (west Africa) the rate of
    unemployement is too high. So the solution of unemployement for me is
    that every student and school boy must be an entrepreneur. So, by the time I leave
    university, I create a little business, the business grow a
    little. That business enable me to pay my rent and to feed myself. By that
    time, most of my friends who didn’t become ‘’entrepreneur’’ like me were
    jobless and were very broke. Even though I did’nt have enough money, they
    admired me and congratulated me of being an “entrepreneur’’. About four
    years later, my little business collapsed and everything fell apart in my life. I lose my
    business and my money.I become very broke. That is a starting point of a
    very, very hard and miserable life for me .I cannot pay my rent, I am in deep debt ,
    I cannot find money to eat. My electricity and water was cut because I cannot pay my bills
    By that time when I fell in misery, most of friends have
    found a job, they started enjoying a ‘’good life’’ (life of security) .They started telling me that:
    “ Yes, we know that, being an entrepreneur is very dangerous and too
    risky, that is why we didn’t follow you in that path. Look, today we have a secure
    job. We are protected by the government. We don’t have much money but we
    have what we need, try to find a job like we do, and forget your idea of being
    your own boss”. I stretch my head and I said to myself,’’I will comeback,
    My coming back will be greater than what I lose”.
    So, most people will never share and accept to be an entrepreneur, most people want security instead of adventure. I‘m still on my journey of being an
    antrepreneur. The journey is hard but it is full of pleasures,tears and lessons.
    I commit to be an antrepreneur. Nothing can stop me on that journey.I make for myself this words of Donald Trump,’’NEVER GIVE up’’,’NEVER QUIT’ Thank you for your attention.

    • Avatar


      Oct 23, 2014 at 4:37 pm

      my dearest friend you are amazing more than the definition of amazing . You are the tiny ray of hope amidst the darkest of darkest gloom not only in my life but to the millions of people all are around the world. 1000 MILLION THANKS TO YOU.

  6. Avatar


    Apr 11, 2014 at 7:08 pm

    Man I totally feel yah, there is only so much we can do for our friends, most people don’t see what we see with this odd lifestyle we acquire to be different in a sense.

  7. Avatar


    Apr 10, 2014 at 11:45 am

    This is perfect. Eventually we all take a different path as our friends create their careers and you create your own, it seems so obvious that different people are gonna want to pursue different jobs.

    This was me at first. I loved the idea of doing it myself, I understood it would be harder than getting a normal job, but to be able to watch something grow from the very beginning sounded a lot more interesting than getting paid to sell sneakers.

    Then I thought, wow this would be so much better if my friends would join me too. Because of what I do, I have different schedules than my friends. When they’re all out late at night drinking, I’m at home sleeping or on my computer.

    It’s not that I want to be out partying, but when a lot of the work I do is at home on my computer, it’s easy for me to miss my friends and wanting to see what they’re up to, working together sounds like an easy solution.

    But the truth is, people want different things. Some people look at me starting a website and think it’s boring, unrealistic and downright dumb. Maybe they’re right. Maybe we’re the weird ones who find working on the internet actually exciting.

    Oh, well. Salute to all you fellow weirdos!

  8. Avatar


    Apr 10, 2014 at 8:28 am

    Wow … actually I find myself in the position of reconsidering my friends to start their own thing way too often. I even abandoned some of my friends because they were dragging me down to the level of no-enthusiasm towards work. However, now I think I won’t do the persuading stuff to my friends anymore.

  9. Avatar

    Mike Sutton -

    Apr 10, 2014 at 4:10 am

    I agree with all 3 points, but I also think career employment as option #1 is on it’s way out. Entrepreneurship is a reality of the new economy and will be the only option for more and more people, so we need to find a way to support, train, and develop those skills in people who aren’t “naturals”.

    • Avatar

      JuiCy™ (@JCDFitness)

      Apr 28, 2014 at 6:08 pm

      I disagree. If everyone were an entrepreneur, who would do the meaningless work? Who would run the errands? Who would make my coffee at the local cafe?

      Who would serve me a steak? Who would make sure my cell phone is working correctly when I have trouble with service?

      • Avatar

        Patrice K. Cokley, MBA

        May 2, 2014 at 6:23 pm

        I couldn’t agree with you more! I’m always having this discussion with someone. Although doing meaningless work is not for us, it is something that needs to be done. Entrepreneurship isn’t for everyone. So I’m ok with people settling in their lives. As long as they’re not trying to talk me out of my goals, I’m fine. Thanks for this post! It came right on time.

  10. Avatar


    Apr 9, 2014 at 3:19 pm

    Cool story bro. But do you even lift?

  11. Avatar


    Apr 9, 2014 at 9:21 am

    Perfect time for this article. I had an argument with my wife last night about issues I am experiencing and she just didn’t get it. She never will either and it’s not a bad thing.

  12. Avatar

    Naomi@business start ups

    Apr 8, 2014 at 8:55 pm

    Hi JC,

    I feel like you hacked my brain. I couldn’t agree more.

    When I first became self employed and earning well, I thought to myself ‘why would people NOT want to do this’. I have tell all my friends and family!

    But in reality although most people lust after the lifestyle they haven’t really got what it takes. They don’t want to work weekends, in the evenings and need a boss to be accountable too.

    They just can’t commit. I now realize this is OK. It’s their choice, their life and everyone journey towards fulfillment and happiness is completely different and doesn’t have to follow mine.

    Great post and scarily close to my own thoughts!


    • Avatar

      JuiCy™ (@JCDFitness)

      Apr 8, 2014 at 10:26 pm

      Thanks. Glad it resonated – I imagined it would with others paving their own path.

  13. Avatar

    Emily Filloramo

    Apr 8, 2014 at 5:31 pm

    JC, I agree that it does take a certain personality to have the tenacity to work through all the fears and obstacles that naturally come up as an entrepreneur. When something great happens as a result of the hard work, it’s euphoric.

    The path to success is not a straight line, it’s full of zigzags. It’s not for the faint of heart.

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