Live Your Legend | Full Disclosure: 12 Reasons You Probably Shouldn’t Be An Entrepreneur (The story no one tells)
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Full Disclosure: 12 Reasons You Probably Shouldn’t Be An Entrepreneur (The story no one tells)

Full Disclosure: 12 Reasons You Probably Shouldn’t Be An Entrepreneur (The story no one tells)

What you dont know about entrepreneurs

“Don’t compare your inside to someone else’s outside.” – Unknown

In Pursuit of the Honest Entrepreneur…

A couple months ago I was wandering around the streets of Mykonos, Greece and came across a little scarf shop. I peeked inside and saw this woman working away. She was so focused on her weaving that at first she didn’t even notice the sunburned foreigner in the doorway staring and smiling.

The pieces she was producing were gorgeous – they covered the walls making the whole shop look like an endless painted canvas.

But what struck me most was the smile she gave when I asked if I could take a picture (I opted to share the one of her working instead of posing). I could feel the warmth in her smile that seemed to bleed right back into the thread as she just kept creating.

She was easily in her 70’s or 80’s, and despite it being 9:06pm, it didn’t look like she had plans to go anywhere for a long time. Nor did I get the feeling that she wanted to. She seemed so at home.

She just looked so damn happy, proud, focused and calm. I noticed myself even a bit envious of how simple her life probably was.

But then I caught myself.

I was doing what I always tend to do – following the pattern most the world does without even realizing it.

For a few moments I fell in the love with the sliver of her life that I was able to see, giving no thought to the rest of the story.

I’m all for being inspired by the possibility of what people do for work, and that’s why we profile so many of them on LYL. Believing in possibility is where the journey has to start.

But what concerns me is that most of us tend to stop there. We give all the attention to the part of someone’s life that represents our own dreams, that we forget to notice what’s real.

And it might be the most dangerous with entrepreneurship…

The challenge is twofold:

  1. With today’s social tools, it encourages people to only post and share the top 5-10% of their lives. And since the spotlight is bigger and brighter the more successful and well-known you get, it only becomes more distorted over time.
  2. As humans observing our surroundings, we naturally seem to assume people have it better than they actually do. We magnify the glamor and marginalize the truth. When these two factors combine, it can be incredibly misleading.

So today I want to offer another look at it. An entrepreneurial reality check of sorts.

Because most of us know the glamorous stuff all too well. That I’m able to write this from a little cafe in a small beach town in Greece. You know about the freedom, travel and adventure. The influence, owning your own calendar, having no one to report to, choosing your own destiny and having unlimited possibility in how you build, create and apply yourself to the world.

That it’s actually possible to double or triple your income in a year (or a month) by getting creative with a new idea or approach. And to do all of this while feeling like you’re actually doing something that matters – and helping people in a unique and meaningful way. We hear about this stuff a lot.

And yeah, like we talked about last week, the possibility is downright mind-blowing, and I’m so damn grateful to be living right now as opposed to any other time in history. I wouldn’t change a thing.

But having false expectations and me painting some BS rosy picture doesn’t do any of you any good either.

Because if you go into it thinking it’ll be a lot easier and more glamorous than it is, you’ll start things for the wrong reasons and probably give up way too early.

That’s not what this community is about. That’s not what you’ve entrusted me to do. It’s about shedding light on the path, on what’s possible – warts and all.

The reality is entrepreneurship isn’t for most people. Sometimes I even wonder if it’s for me. The emotional and actual swings can be crazy – often times they are.

A while back one of our readers asked me…

“Didn’t you ever want to bawl your eyes out at some point back at the beginning?”

So I figured I’d shed some light on the side of the story that never gets enough attention.

crazy people work here

12 Reasons You Might Not Want to Be an Entrepreneur – or at least fair warning of the party you’re joining…

1. My short answer is yes, I did feel like bawling. And at times I actually did. I still get the feeling more often than I’d care to admit. The speed at which momentum can appear and then disappear is hard to get my head around. People doubt me all the time. I doubt myself too. Lots of people around me don’t understand what I do, or why I do it. It can make it hard to relate to others.

2. Sure I can travel more than I used to, but I’m turned on and connected more than I’d like to be. A lot more. Sometimes I miss the days of being able to go off the grid for a couple weeks, but even today if I did that technologically, I’d still be connected mentally, because for better or worse I don’t ever really stop thinking about what I’m building.

3. I constantly have to be innovating and reinventing. I wonder if the way I’m doing things still makes sense or if it’s time to change. I don’t know what this business or my income will look like in a year.

4. And while no job or career is anywhere close to certain, as an entrepreneur I am very very aware of that uncertainty every day. Often times it excites me, but every now and again it brings me to my knees.

5. There is no being off the clock. If things need to get done then you keep working.

6. You often go a very long time before getting any recognition. Almost no one paid attention to my work for the first four years. You have no idea what that can do to one’s confidence and conviction, especially when others are doubting you at the same time.

Gandhi says, “First they ignore you, then they laugh at you, then they fight you, then you win.”

But no one talks about how tough it can be to stomach those first three steps. And that the fourth is the only one not guaranteed.

7. Some mornings I wake up lost in what to do next. Or where to start among the endless and growing list. I can get crippled by the constant decisions, huge and tiny, that must be made with imperfect information.

8. Self motivating can get unbelievably exhausting. Sometimes it’d be nice to have someone to just tell me exactly what to do next.

9. Every day I realize there’s more to learn and seems like there’s less time to learn it.

10. I wear more hats in a day than I thought I’d wear in a lifetime. I got into this business because I wanted to help people find and do work they love. I didn’t realize I was signing up to be part-time manager, CFO, artist, writer, event planner, designer, box checker and box creator. I’m now grateful to have a team, but that still doesn’t make all my hats go away.

11. Your identity can become so tied to your business that it’s hard to distinguish between the two. A decrease in sales or traffic or growth sometimes impacts my own confidence and self worth. Even though intellectually I know one is not the other.

12. Wondering how sustainable the business is can be incredibly terrifying. The pressure of thinking how my ideas will support my family over the years is intense. That can keep me up at night and chase me out of bed in the morning.

If every moment were only like this innocent sign we came across in the little Greek isle of Paros…

no stress be happy

Not exactly. At least not all the time.

It turns out there is a not so glamorous reality of being an entrepreneur, of taking a stand, walking your own line and pursing what matters. And this is just scratching the surface – a mere nibble of what I’ve experienced in the past few years.

And I know I’m not alone, despite how few creators actually talk about it.

I’m beginning to think these experiences aren’t boxes you check as you grow. They’re more like cycles you experience in different ways on different levels along the way.

It’s like the path to mastery… Every growth and progress phase is followed by a plateau. But before the next growth phase there’s a dip. A phase where confidence wanes and you wonder what the hell is happening. Then more progress – at least that’s what we hope.

But don’t worry, this isn’t how it always is.

I pinch myself every day thinking of the possibility I get to be a part of. Of how I get to help and impact people with the work we do – and the meaning and life it’s provided for me and so many others. I’m grateful for all of that on levels I can’t describe.

But you deserve to see both sides. So that when things get crazy, you’ll expect it and welcome it as a part of the path you chose – as part of the party. So you’ll lean into it instead of darting for the door.

And it’s not all about going at it on your own.

I know many of you plan to build your own thing and a lot of you already are, which is awesome. The world needs it!

But remember, loving what you do comes from aligning who you are with the difference you want to make in the world. Whether that’s on your own or with someone else makes no difference. What matters is that it’s you.

Maybe you strike out solo from day one. Maybe you find a partner, or join a business already having the impact you care so much about making. In our lifetime we’ll all likely start with one and end with the other. And then perhaps do it all over again – backwards. It’s all possible. That’s the fun part.

It just depends on how crazy of a ride you’re looking to get into. 🙂


P.S. I was thinking of putting together a little quiz to see if you’re meant to be an employee or entrepreneur. Would that be helpful? Tell us in the comments – and let me know if you’ve experienced any of the above!

  • Michelle Russell
    Posted at 14:50h, 12 August Reply

    Many thanks, Scott, for this post. I’m fairly new to your site, and this is my first comment . . . I feel moved to because what you say here is SO needed. There’s such a tendency to over-glamorize the entrepreneurial lifestyle, but (as you so cogently observed about that weaver on Mykonos), we’re usually getting only a sliver of the real picture.

    One thing I’d add (as someone still in the beginning stages of moving from full-time employment into entrepreneurship) is that a big part of the picture can be fear of visibility. That was one huge takeaway for me from WDS this year. One of the presenters challenged us to make a bold statement–something that we wanted but feared–write it on a sticker, and wear it around.

    I almost wrote something about the specific work I want to do, but then realized that what’s really been holding me back is worry about what will happen if it all goes the way I want it to. Some of those things are the points you make in this post, but there’s also the scary issue of visibility making us **vulnerable.**

    Now that I know I have it, I’m slowly working my way through this fear of being seen. And, inevitably, judged. Because that’s really what’s behind the fear.

    • Joel Zaslofsky
      Posted at 15:18h, 12 August Reply

      Like me, Scott, and everyone else, Michelle, you’ll probably have more time than you’d like before things go the way you want them to. And when the good things happen, they probably won’t resemble your original vision.

      So it’s both a bummer and a blessing that you’ll have time to work through your fear of being seen. But people will judge you. So practice your detachment now. 🙂

  • Joel Zaslofsky
    Posted at 15:15h, 12 August Reply

    I was in the “spotlight” for my mastermind group today – three amazing people focusing their energy and ideas solely on me for 70 minutes – and this is basically how I wrapped up our session: “Sometimes it’d be nice to have someone to just tell me exactly what to do next.”

    I get tired of being my own project manager. I sometimes long for the days when I was someone else’s project manager, getting direction from someone above me. But now there is no one above or below me. It’s just me. Nobody’s going to drudge through the drugery for me.

    But really? It’s not just me. It’s me, you, my mastermind group, the amazing people I’ve met through LYL Local, the How to Connect with Anyone community, the approximately 100 genuine friends I’ve made since becoming an entrepreneur; all who are just *waiting* for the chance to help me out … if only I knew how and what to ask for. It’s the super fans of my blog, podcast, products, and event who – as you would put it – all want to get their fingerprints on what we’re co-creating (and how desperate I want them to be involved).

    As I sit in a house by myself as I type this, I can view my words and actions two ways. Either I’m alone in my own bubble … or I’m one text, phone call, walk down the street, or meditation session away from exactly what I need at any given moment. I’m often the later of the two, but I still yearn for someone to tell me what to do. Making a difference; it’s hard, beautiful, messy, life-altering and everything in-between, right?

    • Scott
      Posted at 09:56h, 19 August Reply

      Amen Joel! I love the alternate perspective on that – the solution is often closer than we realize. Well put!

  • Simon Somlai
    Posted at 22:55h, 12 August Reply

    Great post Scott,

    I believe most of the people who are reading your blog should be entrepreneurs (as matter of fact I believe everyone should “mind their own business” as Robert Kiyosaki says in “Rich Dad, Poor Dad”. Therefore I don’t think a quiz will be a good idea as it will only bring more doubts and questions (IMO) Creating something valuable that is bigger than you is probably something everyone should be occupied with (whether this is full-time or in spare-time)

    You shouldn’t put all your eggs in one basket though, meaning you only build income from one source without a back-up plan. I blog on PD, create products on fiverr and amazon, look to invest my “active income” in passive income streams and have fitness/personal-training as a back-up plan.

    Entrepreneurship isn’t really a job but more a way of life. You learn many life lesson from it. There probably will always be doubts and insecurities on this “narrow road” that no-one really likes to travel as it is composed on endless resistance.

    But I wouldn’t pick any other way of living (and I believe you feel the same way). This is the way that’ll create me in the strongest version I can be in life. A life of least resistance, is a failed life. One that isn’t even worth to live IMO. Do you really want to wonder when you’re older if you could’ve been more?

    Guess there’s things to say about both aspects and it certainly doesn’t take away the pain you get from trying to get the things you want out of life. But what do I know, I haven’t even been blogging for a year.

    Anyway, what did strike me as odd was the fact that you’re wondering if the income from your business will be able to support your family (12). Have you considered spending some of your income on investment property for rentals, stocks or other assets? This might give you a better sense of security.

    Take care Scott, you’re doing great work!

    PS: The comparison of your inner with other peoples exterior reminded me a video about the reality of social media I watched recently ( Great insight on comparing yourself to others

    • Scott
      Posted at 10:03h, 19 August Reply

      Whoa crazy video Simon.

      And I totally hear you about entrepreneurship. At the very least I believe everyone should think and act like an entrepreneur. But people should also be aware of the realities of both sides. Hence this post.

      As for #12 – yup we’ve got investments and things spread around (I used to run an investment fund before LYL ;). I was talking about the fear and uncertainty around if what I create will always be what people want a need. All part of the roller coaster :).

  • Anna
    Posted at 06:09h, 13 August Reply

    How funny Scott, the article I read just before your post, by total chance was about 20 hardest things for small businesses, where it said “It’s way less sexy than you think it is.” So true.

    I’m experiencing most of what you talk about and when working on something switching off becomes an issue. The close ones pay for it, which is horrible as you become My Business Zombie.

  • David Harbour
    Posted at 06:20h, 13 August Reply

    Hi Scott,

    All of the above and more, and I don’t even run my own business at this point, and certainly the reason I continue to procrastinate about doing so. I wish more people would open up about their personal doubts and challenges, it would draw people closer to know that those they follow are hu8man, just like the rest of us. All too often those whom we follow seem like they have it all together and people wish they were more like them, not realizing that they are!

  • Toney Sebra
    Posted at 06:28h, 13 August Reply


    Thanks for sharing this. I have been very unhappy in corporate america and with this community after trying to move forward in my life I quit. The feelings you describe are endless right now as I endeavor and thanks for sharing as my craziness and anxiety are real but its good to have it validated.

    I appreciate your willingness to put this necessary project. Everyone wants more meaningful lives and it is a great endeavor. You are making a difference out there and in me.

    Thank you for the push and community to support the desire for a better life, career and possibilities.

  • Dave Ryan
    Posted at 07:06h, 13 August Reply

    Thanks again for a thoughtful and insightful post. With sites like Facebook, I think we’ve all become accustomed to making vast judgments on very little information. Seeing someone successful and assuming the rest of the story is human nature, I guess.

    Thanks for opening up and showing the other side of things. It’s good to know more of the story before making the leap.

    As for the quiz, I actually don’t think it would be helpful and could end up being just the opposite. Just reading posts like this can tell someone if they have what it takes for entrepreneurship. Although, I think everyone has the potential. It all comes down to the choices we are willing to make.

    Thanks again, Scott!

  • Mike Goncalves
    Posted at 07:11h, 13 August Reply

    As always, great information Scott. Thanks for your honesty and candor when it comes to being real and exposing all facets of what it means to be an entrepreneur. This is certainly a post every single person looking to become and entrepreneur needs to read. They all resonate with me, especially #8. #9 for sure as well. Thanks again, cheers!

  • Vicario
    Posted at 07:14h, 13 August Reply

    Yes please provide us with the quizz you suggest on entrepreneurship. Thank you.

  • Marcus
    Posted at 07:18h, 13 August Reply

    Hmmmm….That’s a very good question.

    On a really bad day I’d suck at both… at being an employee, and at being a business owner.

    The one main reason I got to work for myself is because I feel most motivated to do my best work when I have autonomy to do get the job done, without someone checking in on me every 10 minutes, I always found it off crippling…. When you work for yourself you HAVE TO do a good job to stay in business.

    plus I’ve learned far more by working for myself than i ever did from formal education, or employment.

  • Kristi Battalini
    Posted at 07:36h, 13 August Reply

    Scott, thanks so much for this post!! I have dreams of one day becoming my own boss and of course there is a lot of fear and doubt in even thinking about it yet there is also this feeling deep down in my gut telling me that I have to make that leap. At first when I read about the quiz my initial reaction was “of course” a quiz would be perfect, a quiz would let me know if I am meant to be an entrepreneur. It would eliminate any doubts I may have. Then I realized that taking a quiz is not going solve any problems or eliminate any doubts I have. Taking the leap from a secure job to venturing out on my own to “Create something valuable that is bigger than you” as Simon put it, has to come from a place deep inside.

  • Jennifer
    Posted at 07:43h, 13 August Reply

    Thank you for such an honest point of view that shows the underbelly of entrepreneurship. I will be sharing this with my community and saving it for those times when I feel like I’m out on a limb and second guessing every move I make. You’re a gem Scott 🙂

  • Mike
    Posted at 07:46h, 13 August Reply

    To answer your last question, I think a “quiz” on “should you be an entrepreneur or employee” would be FABULOUS. Because, like most quizzes, the answer won’t be a simple “Yes” or “No”, but a gradient, showing various degrees of affinity to either side. This allows people to think for themselves … “hmm, I’m in the middle, with a slight leaning towards entrepreneur, maybe it’s something to think about” or “wow, I didn’t know I was so comfortable with being an employe. Entrepreneur sounds exciting, but maybe I should give this a second thought.” etc.

    Honestly, that was one of my concerns when I really got into the LYL site. All the marketing material talked about “do the job you love”, but when I got into it, a LOT of the material and success stories talked about creating your own business. Sure, the FAQ does have an entry for that exact question, and the answer is rightfully “no”. Also, the material does say you don’t have to switch immediately; bills to pay, families to feed, etc. Do it a little at a time. So there is “wiggle room”, so to speak. But the overwhelming message seems to be around entrepreneurship. And I’m not so sure that’s for me. I want to do work I love, but I’m not all that excited (and downright nervous) about entrepreneurship and starting my own business.
    Such a quiz would help me to see if this is “just nerves” or something more fundamental/ingrained.


    • Katja
      Posted at 14:11h, 13 August Reply

      That’s a very good point, Mike. And thank you for finding the right words for my gut feeling about LYL – me too, I want to do what I love but am not very excited about entrepreneurship. And maybe the two do not always have to be connected. Some things you love maybe cannot be turned into a successful business. Or if you can turn them into a business, then maybe due to all the pressure and all the needs you’ll stop loving what you do. Or having to be successful with the things you love makes you unable to do them in the right way.
      I would appreciate the quiz too.

  • Alexis Meads
    Posted at 08:23h, 13 August Reply

    Great post, Scott!

    I, too, got married and traveled in the wonderful Greek Islands for a few weeks in May/June. I loved the simplicity of life there. The days spent lounging, eating, swimming, enjoying the sun and the company of others. The irony is that even though I was “doing” less my business was rocking there. I pledged that when I came home I’d continue that lifestyle…and yet somehow I seem to get caught up in the complication and demands of life and entrepreneurship almost inevitably. Since I returned, I’ve yearned (emotionally and physically) for that simple, wonderful place in Greece. But as you pointed out, no one’s life on the outside is as it seems. Things go in cycles and phases. Being an entrepreneur myself is both exciting and terrifying. Thanks for shedding light!

    Alexis Meads

  • Ana
    Posted at 08:44h, 13 August Reply

    Great post, and super timely for me. I’m neutral on the quiz – I think I get a lot more out of articles like this than I do out of taking quizzes, but maybe that’s just my style.

    I think the last point is the most important for me to hear today – the solution might not be starting your own business, and it also might not be designing your business to stand as your only gig. For me, my business is designed to complement my day job, long term. Making art is fantastic, but I need some steady trickle of work to balance out all the creative stuff to keep from going nuts. In the long run, I might dial back my day job more (from 80% FTE to 50%), but I will very likely always have a day job. Which is okay. It’s not for everyone, but for me, it balances out the uncertainty in #12 enough for me to enjoy the entrepreneurship for what it is.

  • Calynn
    Posted at 10:52h, 13 August Reply

    I have experienced all of those over the past few years! It’s really comforting to hear someone more successful saying those things.

    To be honest, I think such a quiz would be silly, too limited, and probably misleading. Then again, I think that about quizzes in general and I don’t think anyone should be an employee. Some people (possibly myself) are better suited to being the idea guy and not the marketing guy or vice versa, but I don’t think anyone should be a traditional employee in the way that it usually works in U.S. today.

    Thanks for the reminder. I know this will never be easy, but it is totally worth the search for the “work I cannot not do.”

  • Ed Rowell
    Posted at 11:32h, 13 August Reply

    Scott, I would love to see a quiz. I’d like to know what questions I’m not asking of myself that I should be. Great work, thanks for the gift you are to others!

  • Lara
    Posted at 12:04h, 13 August Reply

    Thanks for this Scott! I so appreciate your honesty about what it’s REALLY like! Even though I’m just at the beginning my own venture, and haven’t been able to give up the day job just yet, I can already relate to so much of what you have said here!
    We can learn so much from other people’s experiences. Especially when then are a true reflection of reality.
    Here’s to authenticity and vulnerability! Kudos to you!

  • Martin
    Posted at 12:38h, 13 August Reply

    Thanks for sharing this Scott. It’s like you were reading my mind, talking about my own entrepreneurial experiences over the past 9 years. Much needed right now as the doubts are welling up in my newest venture.

  • Dave
    Posted at 15:53h, 13 August Reply

    Thanks for the write up Scott! Very refreshing to have an honest look at building a business. Sometimes I feel there’s so much ‘rainbows and unicorns’ painted by coaches encouraging people to go into entrepreneurship its refreshing to see the whole picture painted out 🙂

  • Jacque
    Posted at 17:18h, 13 August Reply

    Hi Scott,

    For a while, I was reading several “break out on your own” entrepreneurial bloggers. Now, I’m pretty much just down to yours. I still read Leo sometimes, but for learning to be calm, and Altucher sometimes for his honesty and zany ideas. But you–you have me for life simply because I feel the authenticity in your writing and I believe in you. I believe you are making the world a better place. You make me wish that idea would strike me sometimes just so that I could give back to you by my own success and tell the world that it started with Scott Dinsmore and LYL. Of course, there is more to it than that, but honestly, when I read your posts, I feel that.

    • Scott
      Posted at 21:33h, 13 August Reply

      Whoa Jacque! Thanks for this. What a wild comment to read – you have no idea. Showing you all of who I am has always been one of my leading values at LYL and knowing that you can feel it means so much. I don’t think it’d be fair to do it any other way. It’s an honor to have you here and I cannot wait for the day you “give back to me with your own success.” I know it’s only a matter of time! And probably not too much time at that…

  • Kai
    Posted at 17:47h, 13 August Reply

    Hi Scott,

    What a most lovely picture of you and your wife. You guys are wicked…thanks so much for your never-ending supply of superzest and mojo….you make for one heck of an example. A good day to you fine sir.


  • Daniela
    Posted at 19:16h, 13 August Reply

    Thank you so much for this post. It was exactly what I needed to read right now. I’ve been struggling to stay motivated in my business, and a lot of what you wrote feels so relevant to me. It’s inspiring to know that even you, a massively successful and inspiring entrepreneur, feel doubt, fear and discomfort sometimes. It gives me the strength to keep forging ahead. Thanks for your honesty and vulnerability.

  • Vieri
    Posted at 21:09h, 13 August Reply

    Robert T. Kiyosaki in this book: analyzes the differences between the four kinds of workers: employees, self employees, buisness owners, investors.

    About the 12 reasons, these are some of the reasons why i question few things: money, capitalism, enterpreneurship among others. I did and i’m doing some resarch about alternatives. I discovered a lot but still i have to apply many things to my own life.

    Thanks Scott, i love the fact that you are the first in applying the “be you, be real, be open” approach.

  • Kyle
    Posted at 01:29h, 14 August Reply

    I’d be interested to see your employee/entrapenur survey.

  • Kshitij
    Posted at 04:02h, 14 August Reply

    My journey started two years ago. LYL was the first site which actually motivated me to make the leap of faith.

    After that, I made lots of connections with fantastic people out there.

    Looking at where I’m now I just realized how fortunate I am. I’ve experienced many of the things you’ve mentioned, and the support system I have has just made it so much easier.

    The highs though, may not be so awesome as yours, but are definitely as ecstatic.

    But I would never have commenced this journey if I hadn’t stumbled upon, and become overwhelmed by your site that day 2 years ago.

    And for that I am truly grateful Scott 🙂

    • Scott
      Posted at 10:14h, 19 August Reply

      Wow – what an honor to hear. And I’m so glad you stopped by two years ago. Keep us posted on the journey!

  • Sebastian Aiden Daniels
    Posted at 09:09h, 14 August Reply

    A much needed post for me to read. I am glad that I am not the only one who bawls there eyes out every once in a while, at least once a week for me sometimes. I definitely feel intense anxiety more than once a week, which is tough, but you just feel and accept it.

    You are right that being an entrepreneur sucks. As you put it, you tie your self worth to your success, so your mood goes up and downs with the growth of your business/blog and at the same time it “will never be enough” right?

    That it is scary it took four years before people started to take notice. I hope it doesn’t take that long for me, but I understand that it is a perseverance game and something you have to do for the long haul!

    Thanks for the reminder that as crazy as being an entrepreneur is and that many people might not understand it, that it is still worth it in my mind!

  • marios
    Posted at 12:53h, 14 August Reply

    I would love to see a valid quiz that could help me understand if I am more an employee or more and entrepreneur.
    Keep up your excellent work scott.
    I am always looking forward for your next e-mails.
    And I am slowly but steadily building inside me the confindence to build something tha suits me better that what I am doing today.

  • Deb S
    Posted at 14:01h, 14 August Reply

    What a wonderful introduction to your site, Scott! Thank you for reminded me that all of us go through our ups and downs in our never ending journey to bring brighter lights to this world.

    May you continue to ignite the best in people! You’ve certainly lit my fire brighter and I’m looking forward to absorbing all the information you have here. 🙂


    • Scott
      Posted at 10:15h, 19 August Reply

      Welcome to the adventure Deb – so glad you’re here!

  • Kyle
    Posted at 14:53h, 14 August Reply

    Wow Scott. Did you write this about me?

    Totally hit home.

    P.s. Awesome meeting you at WDS last month. Hope your voice recovered ok 🙂

  • Satish
    Posted at 23:43h, 14 August Reply

    Thank you for letting me know the other side of the coin Scott. I always thought doing things I love would make my life easier and may be that’s the reason I’ve been trying to find passion in easy things and put off tasks that seem difficult.

    Thanks for letting me know that I have to work hard to make a difference, to do things that matter. I understand that from the outside everything seems pretty, I’m going keep this in mind and move forward…!!!

    ” Courage is not that you do not have fear, courage is feeling the fear and doing it anyhow. “

  • Jamie Lazar
    Posted at 09:20h, 15 August Reply

    Such a refreshing post! One of my favorite sayings is “we are more alike in our weakness’ than our strengths”. Scott, this post came from your soul, and you have obviously impacted a great deal of people (including me) with your writing. Because you were open and shared this, it reminds me again that I am not alone as an entrepreneur. It takes a different mindset to run your own company and often it can feel like a very lonely road. The reality is, as business owners, we have all experienced these 12 things, and by discussing them we can link arms and help each other through those tough times. That is the beauty of humanity! Thank you for your words, please do not stop doing what you do as it is much needed!

    • Scott
      Posted at 10:17h, 19 August Reply

      And that is exactly why transparency is so important to me Jamie. I’m glad it connected!

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  • Rebecca
    Posted at 12:35h, 15 August Reply

    Rather than a quiz, I think what your site might need is more articles like this one! It’s important to tell people that self-employment sucks sometimes, and it’s okay to feel that way, and that some things about traditional employment are just better and easier, and that’s OK too, and it’s a matter of working through the sucky parts no matter which way you choose!

    What about maybe an occasional post just like this one, where you talk about problems and obstacles that have been getting you down, and how you dealt or are trying to deal with them? Like your post about the standing desk — a productive project you were really excited about, but that had to be ended. You can talk about the good and the bad, and show people that this is normal life in self-employment — not just the blogging from Greece, and not just the part where you’re broke with no way out.

    Really, I’m telling you, tons of bloggers DON’T do this. Pat Flynn at Smart Passive Income goes so far as to post his monthly balance sheets and talk about which projects are moving and which aren’t and why. James Altucher is of course famous for bleeding his failures out in excruciating detail. But it’s surprisingly rare to see anyone else talking about the good and the bad of self-employment as a cycle or a continuum, not as just “it’s super awesome, everyone should do it!” or “it’s terrible and you’ll probably fail, nobody should do it!”

    • Scott
      Posted at 10:20h, 19 August Reply

      Great point Rebecca! I will definitely see how I can find a way to give this side more attention and analysis in the future. Thanks 🙂

  • Daniel
    Posted at 01:43h, 16 August Reply

    Wow, thanks so much for sharing this with us Scott. It really is hard to be an entrepreneur, however, I have never felt more free and more living on purpose.
    Thank you for showing your vulnerable side which always brings along risk, especially once you become as popular as you. But it also creates immense connection with the one’s you are meant to serve.

  • Kara Lane
    Posted at 06:22h, 18 August Reply

    Hi Scott. This is my first visit to your blog, and your entrepreneur reality check article came at a perfect time. I could especially relate to #6 about how long it can take before getting any recognition. I’m in the “first they ignore you” stage…which sometimes makes me want to run back to the “security” of corporate as fast as I possibly can and pretend I was only kidding when I left to follow my passion! Re your question of whether it would be helpful if you put together a quiz to see if we’re meant to be an employee or entrepreneur, I’d vote yes with one caveat. The caveat would be to have a disclaimer, like: If you are REALLY passionate about becoming an entrepreneur & are willing to put in the time & effort, then go for it regardless of what the quiz shows. I’ll never forget years ago a fellow CPA was raving about this entrepreneur we knew, and he turned to me and said, “You and I could never do that.” It took me a long time to work up the courage to challenge that assessment.

    • Scott
      Posted at 10:22h, 19 August Reply

      Well I’m glad to hear you worked up that courage Kara – something tells me the world needs it! And awesome to have you here. Welcome to the adventure! Lot’s of fun (and full disclosure) to come…

  • Kelly
    Posted at 16:21h, 18 August Reply

    Great post Scott and very timely for me. I have been running my own business now for three and a half years and can completely relate to everything you said. In the last year I have come to realize that I no longer have any passion for the area I am in but, am wondering if it is also that running a business and being an entrepreneur is not for me, and perhaps I am better suited to being an employee or, wether if I find my passion this will change. I worry that after working for myself I would really struggle to be an employee as I value my freedom and control over my own life very highly.

    I would definitely be interested in the quiz!

  • Andy
    Posted at 04:00h, 19 August Reply

    Scott – well done and thank you for sharing those thoughts. I’ve been running my own business for 12 months now, I’m happier than I’ve ever been but the journey has been so different to what I imagined – and touched all of the points you’ve made.

    6 months ago we were reviewing things and my partner asked “are you sure this is working?…” Tough question. And the only truthful answer was “No. But I’m sure it’s the right thing for me to do…for all of us.”

    6 months on, income has quadrupled, leads are building but more importantly I have a real sense of opportunity and excitement at what the future holds.

    But, I think we owe it to everyone who asks to make sure that no-one goes into business for themselves without knowing about your 12 points and in particular that motivating yourself everyday is tough, and that of Gandhi’s 4 points only the first 3 are guaranteed (I love that!)

    Keep up the good work Scott


    • Scott
      Posted at 10:24h, 19 August Reply

      Wow Andy. I absolutely love that answer. And then that you continue to prove yourself right!

  • Joseph Jameson
    Posted at 11:23h, 19 August Reply

    Having a quiz available would be great, mostly because I think it would save the people who think it would be great to have their own business in theory, but not in practice from making a very costly mistake. A friend I went to high school with, refinanced his home, sold their RV, and the entire family sold everything that wasn’t strictly necessary in order for him to begin his business. When it went belly up for a variety of reasons that really boiled down to the fact that he was better at getting the work done than overseeing the entire business, it left him unable to recover financially, and filing bankruptcy was all he had left. We never stop learning, so the best course is usually to read up as much as any of us can, from places like this, and other people who have become successful, to give us the best chances we can get before we go it alone. Glad to have resources like this around, and will take part in workshops for sure.

  • Anuradha S
    Posted at 02:22h, 20 August Reply

    That read like the story of my life! It was a wonderful recap of everything I’ve been through ever since I decided to strike out on my own. I was at the “bawling my eyes out” phase when I stumbled on this blog, and it definitely helped! I’m back on track now, thinking about new products and promotions and sales and inventory and finance and logistics and…!

  • Sasha
    Posted at 10:57h, 20 August Reply

    Yes please! I would love a quiz about whether you are meant to be an employee or entrepreneur -or maybe both

  • Zoe
    Posted at 11:32h, 20 August Reply

    Hey Scott,

    I don’t always read your posts, but I really appreciate this one. I’ve been working as a freelance journalist, and while maybe I haven’t got the business angle yet, so many of my experiences correspond to what you write about. Not only because of my work life, but also because of the personal choices I’ve made in life — like dropping out of college and then going back 9 years later — I resonate with what you are saying about it being important to align who you are with the change you want to make in the world and making decisions from there.

    Anyway, thanks for the work you are doing and for the encouragement you are giving people to live in a way that is true to them. And for this kind of reality check because it is not always a smooth journey.

    All the best,

  • Dayv
    Posted at 23:07h, 22 August Reply

    Definitely going with DOOR #1 🙂
    I found #8 and #11 very relevant for my current circumstances, got a business mentor, and he has put me onto you 🙂

  • Ellen
    Posted at 08:09h, 23 August Reply

    Wow Scott. Thank you for your honesty. It is always reassuring to know that we’re all in the same boat. I wish you continued guts and courage! (oh – and success too! Keep on keepin on!)

  • Ellen
    Posted at 08:23h, 23 August Reply

    Regarding an “Employee versus Entrepreneur” survey – –
    My thought is that it mustn’t be an either/or proposition.

    For me, I am an employee, and I am having a hell of a time finding my inner entrepreneur. I think I am an employee because that is my training. Most of education and social expectation is geared toward fitting into that employee role.

    Finding my inner entrepreneur is a growth process, and a daunting one at that. There are days where I’ve read an “Employee versus Entrepreneur” type article, and it made me think that there is something to that. Maybe I’m just somehow not meant to be entrepreneurial. However, the universe indicates otherwise – by not giving me a job (and believe me I keep trying).

    So here I am, a highly trained and educated cog-in-the-machine employee, trying to wake up my inner entrepreneur. I know she’s in there – buried by layers of social conformity and people-pleasing maybe – but she’s in there!

  • Chris Banzet
    Posted at 08:32h, 23 August Reply

    GREAT piece Scott! One of the greatest misconceptions is the “journey” into success. It doesn’t always have proper road maps or signs, sometimes the compass looks like you’re heading south instead of north, and when you turn to look at the largest bump in the road you just hit, you run smack into the largest wall you’ll ever hit.

    There is no rhyme or reason, only the sheer intention which has a laser focus of where you want to be. If you’re a sprinter, you’ll die a short, quick and expensive entrepreneurial death. If you are ONLY a dreamer, then your fantasy will become a nightmare.

    However, if you are someone who has a deeply routed internal compass to get to a certain point, and you’re flexible like a palm tree in a hurricane, faithful enough to endure the black eyes, aching back, overwhelming pressure, and enjoy working for pennies at the beginning, you might just have a chance.

    In life there is two types of events which happens to us. Those which we “accept” and turn into learning experiences and those which we cannot accept that become “brick walls”. If your map has a straight road to your dream, then you’ll probably never see it. But if you pack your traveling bag with the “acceptance” that it will never be a straight path, you just might find yourself at the top of that beautiful mountain! 🙂

    • gail
      Posted at 18:32h, 20 December Reply

      Chris, great analogy about the learning experiences vs the brick walls in the entrepreneurial journey and in life.

  • Michelle Grace
    Posted at 10:04h, 23 August Reply

    Good morning, Scott and the LYL community!

    I just finished reading this blog post (while a little fear sneaked in :). I wondered if what I’m doing is the right career for me. I’m an artistic entrepreneur, I hand make floral and ribbon leis and I totally agree! Being an entrepreneur is an emotional roller coaster, I wonder sometimes if what I’m doing is my passion, as I’m passionate about a lot of things.

    But…As I was reading the first few paragraphs it inspired ideas and a new perspective of what I’m doing in my business. Thank you for that! After I jotted down my ideas, I continued reading and every reason you listed, I can relate to. Each one I read through, I said to myself, “YEP! That’s me!” And it reassured me that I’m not alone. There are days, sometimes weeks I bawl my eyes out and question what did I get myself into. But then I realize that this is what I love to do and it makes me happy to see my customers happy and excited to find our leis. That’s what inspires me to continue, I love seeing others happy. And I realize that I love the challenges I face as an entrepreneur. I enjoy learning new things about business and creativity. It inspires me to grow and evolve as a person and entrepreneur. So, I will not give up. And now I realize, I’ve chosen the right path for me.

    Mahalo (Thank you)!

    ~ Michelle

  • Kevin
    Posted at 13:34h, 23 August Reply

    I think a quiz can be useful and enlightening sometimes, but honestly I think making decisions about your life from a quiz is not the best approach to take. When I was young I took lots of career and personality tests to confirm my dream to be a pilot. Almost every test I took did not list “pilot” as a good choice. I worked a few years in a desk job which I thought was more suitable. All I did each day was look outside and stare at the airplanes flying in the sky and wonder if I made the right choice. Finally, I decided to follow my heart and leave the cubicle life for the cockpit of a helicopter. I couldn’t be happier even though no “job” is perfect. The point is that if you want to be an entrepreneur, just do it! The worst thing that can happen is you go back to your old life if you find it isn’t for you.

    This post is actually very relevant to me right now and I thank you for writing it. I’m on a sabbatical from my perfect flying job as I want to spend more focused time with my family and do some travel overseas. I’m considering going out on my own and helping my wife with her new business as well.

    The funny thing is that the positive 10% I would tell the stranger on the street makes things seem amazing right now. For example, we’re flying out to the South of France end of September (one way), we rented a small house 15 minutes from the Mediterranean Ocean, and right now we are preparing to leave to visit family on the East Coast.

    So what is the other 90% like? Not as much fun. Stressing over whether our house will sell before we go or will we have to rent it out? Trying to balance my wife’s business tasks with the things I want to do. Lots of planning, putting things in storage, starting to homeschool my son this year, will we run out of money?

    Compared to when I was employed as a pilot, our life now seems chaotic, stressful, and so disorganized. In other words, the future is very uncertain. When you are an employee you know your role in the world. You have a routine. You have a steady paycheck. There have been many times recently I have been frustrated and just tell my wife, “I’m going back to work!!”.

    I am mostly happy with our decision to take a sabbatical but it has been a huge adjustment and I hope things will settle down once we get to France. We will have less household distractions, more time to focus on the kids, and each other, and time to build my wife’s business. I’m still planning on going back to work in a year or so just because I love taking to the skies and I may need a vacation from the life of an Entrepreneur :))

  • Jeff Bronson
    Posted at 11:07h, 24 August Reply

    Good points Scott!
    Often the beginnings on an entrepreneur’s tale is lost in the shuffle. We only see the good parts. Yet, an ‘over night success” may have taken a decade.

  • Bernadette
    Posted at 07:42h, 25 August Reply

    You hit the proverbial nail on the head! I was just having this conversation with a dear friend who wants to be an entrepreneur. I kept pressing for his “why”…looking for the passion…I found your “why” gets you through the valley of this entrepreneurial journey. This message so resonates with me…one of my mentors, Jonathan Fields, shares about the time in The Thrash…it’s so where I am right now…which consists of several of the things you mention in this blog. I truly believe my ‘revolution’ is the right thing on a cellular level…which is what is carrying me through my Thrash. Thank you for balancing the scale and for bringing the other side to light! I love my business, the difference I make in the lives of leaders and organizations and I wouldn’t change a thing…it’s all a cycle!

    • Ellen
      Posted at 07:59h, 25 August Reply

      Time in “The Thrash”, eh? That sounds like a useful concept 🙂

  • Christina
    Posted at 10:23h, 26 August Reply

    The entrepreneur vs employee test would be a good start for me to settle my focus issues on where I should be making my next move. I am also farily new to the site and the LYL concept. Already been sharing this great material because I find that I am not the only one in a pivotal decision about this. So seems like we are many unorganized ambitious persons wanting to get some great tips on moving forward and start making some concrete decisions.

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  • Joan Harrington
    Posted at 13:12h, 05 September Reply

    Hi Scott,

    I am new here and definately will be sticking around!

    Great post! Such fantastic value that you put out and for that thank you:) You are one of the few who are real and authentic 🙂 I decided to get on your email list as I enjoy your site very much 🙂

    Some are just not cut out to be an entrepreneur and so many quit way too soon before they even make a dent expecting to “get rich” over night…..cracks me up that there are so many that are like that and when that doesnt happen, they move onto the next shiny object……and for those of us who are, you have shared some wonderful insights into the world of entrepreneurship 🙂

    Thanks again,

    Take care,

  • Rich
    Posted at 12:51h, 17 November Reply

    Hi Scott,
    I appreciate your honesty about the difficult times as well the good times when it comes to running your own business. I hadn’t signed up the course yet but will now because of the fact that you revealed the possible ugly and aren’t just selling the pie in the sky solution to financial freedom and bliss. Anything worth having is worth fighting for!

    Looking forward to the journey!

    Kind Regards,

  • Jen
    Posted at 13:00h, 26 November Reply

    Please make a quiz like that. I think it’ll be very helpful for a lot of people!

  • Peter Bock
    Posted at 13:13h, 03 December Reply

    I’d love the quizz, could be fun to see what it says about me, especially since I handle stress — combined with a deadline — SOO well (read: complete and utter panic attacks that leave me too empty headed to feel dismayed, or even work on, the project/exam for a while…). 🙂

  • lreneec
    Posted at 11:27h, 12 December Reply

    Hello Scott!
    Though a quiz might be helpful, I also think it might discourage me if I happen to get an answer I wasn’t expecting. Whats the difference between letting go of things not meant for you, and pushing beyond what you think you can do?

    • Tee
      Posted at 12:12h, 02 May Reply

      Great point

  • Selen Yılmaz
    Posted at 15:09h, 04 January Reply

    Hey Scott! I really appreciate what you have achieved so far and keep inspiring people to follow their dreams! I want to say a huge thank you for all your support.
    Selen x

  • Astrumiss
    Posted at 06:31h, 03 February Reply

    Hi Scott. Since I love quizzes, a quiz about whether we are meant to be an employee or entrepreneur would be fun. But to be honest, I think the list of warnings/reasons to think twice if one wants to become an entrepreneur would make it pretty clear for the person if he/she would or want to become one. If the warnings are intimidating, he/she will just turn away and walk off. With that said, I would like to end my comment with a quote from Randy Pausch’s The Last Lecture: “The brick walls are there for a reason. The brick walls are not there to keep us out. The brick walls are there to give us a chance to show how badly we want something.”

    Thank you for the bricks, giving us the chance to show ourselves how badly we want to be an entrepreneur.

    *For the ones who would like to remember or watch for the first time his lecture about “Really Achieving Your Childhood Dreams”, here is the link =>

  • Zoom
    Posted at 06:59h, 22 February Reply

    It can be a very lonely road. I understand and accept that now. I’m working full time and have begun taking action after hours. People at work don’t relate much. I have to pretend I also want to climb the corporate ladder and buy the most expensive car when bonus season comes. I’m very greatful for discovering awesome communities like this one cause I was honestly starting to think that I was losing my mind. This post is sincere and honest. I have found my tribe. I will live my legend. Thank you for the value Scott.

  • Ben Day
    Posted at 21:50h, 02 March Reply

    I’d love a “Should I be an Entrepreneur?” quiz, but I worry about the reliability of self assessments and the seemingly pass/fail nature of the question. Is it possible to find varying degrees of entrepreneurship, what “level of leader” you’d like to be (Thanks, Orrin Woodward), and some way to ask questions that exist more along a sliding scale, (very like me to not at all like me) including factoring in response times (a la Strengthsfinder2.0)? Just some thoughts!

  • lou
    Posted at 08:25h, 05 March Reply

    Hi Scott, you seem to come from a well-off family. So you have stress about future and all that but im sure you´ve got quite a cushion if anything falls apart. Correct me if im wrong.
    What would you say to people who does not have that privilege?

  • Dan
    Posted at 11:49h, 12 April Reply

    ditto on below post!!!!!!!!!!!

  • dandy trooper
    Posted at 13:20h, 14 April Reply

    I once had a job making about $10 per hour. An appointment complained because we were late. They said that because they made $200 per hour they couldn’t afford to wait for us. I found it ironic that they thought because they made so much money they couldn’t take time off. On the contrary, making a low income meant I couldn’t afford to take time off, if I did, my rent wouldn’t get paid or I wouldn’t be eating that week. I understand the numbers are more valuable for the customer, but the point of a lot of money is more freedom, not more work.

    I find it interesting how perspective changes with success. How many rich people think their business can’t stop because of how much they are missing, when if a low-money person had a fraction of that the first thing they would do is take time to travel and take a break.

  • T
    Posted at 12:11h, 02 May Reply

    I would love to take that quiz!! I always wonder if I’m cut out to be an entrepreneur. The thought of not having a stable income scares me away from trying anything even though I hate corporate life & know that it’s not guarantee either. It does give a false sense of stability though.
    Thanks Scott!

  • Jeremiah
    Posted at 06:33h, 29 May Reply

    Thanks Scott for sharing. You’ve got a very important point there. Life indeed has two sides to it just like a coin having a head and a tail. It’s good to know both sides to being an entrepreneur before committing to it..I see entrepreneurship as a challange and an exciting phase in discovering more about myself and how I can make the world around me a better place.

  • Me Too
    Posted at 19:01h, 09 July Reply

    Yes to the quiz idea

  • Walter Eggers
    Posted at 22:35h, 26 July Reply

    Scott, Thanks for the insights and the community. You are a true inspiration and I love that your passion is to help others find theirs. A humble Thank You Sir… I don’t think a simple check-box, black and white, yes or no type of quiz would be helpful at all. In fact, I think it would be wildly inaccurate and ultimately detrimental to those who have entrepreneurial desires. If the question is simply employee or entrepreneur then the answer is logically employee. It’s way easier and it is secure- that is logical. The entire purpose of this site is the opposite of logic, it’s passion. I believe your entrepreneurial story is a perfect example of this. Finding passion in what you do was never about a yes or no option, it is a dynamic journey. A journey which you yourself didn’t know the outcome or the destination until you made the decision to not follow where the path led. Instead you forged your own path led by the compass of your heart. You discovered your ultimate legend by way of the journey, and that’s the point. There is no rubric for entrepreneurs. The person is shaped by the journey and led by it’s lessons. Entrepreneurship is for those who hear people say “no” to an idea and; not only, know differently they are thus motivated to prove otherwise.

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  • Eugene Howard
    Posted at 13:07h, 15 February Reply

    So I have been an entrepreneur and employee, both have their ups and downs. The one reason I stopped my last business was my family did not like the feast or famine my work seemed to go through. So if I decide to go back that route that is something I will have to consider as well. I think a test would be great. See if time has changed me attitude towards it.

  • Tanner L Jewett
    Posted at 16:41h, 23 February Reply

    I would rather you shared how you deal with these things. What have you found helps you the most?

  • Errol
    Posted at 23:06h, 01 March Reply

    Hey Scott! Yes, that would be really helpful. I’m constantly battling myself over whether I can really handle the whole entrepreneurship thing or whether a day job is better. It’s doing what you want to vs doing what you can do well (did that even make sense? :P) So a quiz or checklist of some sort would be really helpful. Keep up with the great work.

  • Nailea
    Posted at 09:11h, 14 June Reply

    It’s great that you talk about the hardships of entrepreneurship. I appreciated reading through this and definitely connected. I see this if from 2014 and i’d love an updated article with 3 more years under hour belt.

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