10 Things You Need to Give Up to Be an Entrepreneur

10 Things You Need to Give Up to Be an Entrepreneur post image

There was a nice post about being happy that was everywhere on Facebook last week. One of my favorite bloggers, Rob Walling, did a great job of adapting it for entrepreneurs on his podcast. It got me thinking of some of the things I’ve given up in order to build a business. Here they are:

1. “Success.” I wasn’t able to quit my job until I gave up on the vague ideas I had about success. Stuff like having a good job and making a good salary. I remember saying to myself: it’s possible that nobody will ever think you are successful.

When my answer was finally “screw it,” I quit. At the time I did not realize how fulfilling it would be to work directly with customers and products I was passionate about.

2. Over-worrying about screwing up people’s lives (or being perfect for your customers). If you try to make meaningful change with your business, you will create collateral damage. Period. Even relatively benign assertions like: “if you want to make some extra money on the side, try building some niche sites” can waste a year of somebody’s spare time. I’ve seen it happen. Seems harmless, eh?

3. Reliance on cultural scripts for decision making.  I’ll share something embarrassing: one of my biggest concerns with following the entrepreneurial “weird expat” path was that I wouldn’t be able to find a wife. The cultural script I was working off of said something like: position yourself in a nice secondary US city, have a high-quality job, and watch the wife candidates flow in.

To hardcore entrepreneurs, this might sound like a petty concern, but to me it was a meaningful fear I had to overcome. I know more than one guy who never followed his dreams of being a musician or of traveling abroad or of starting a small business because they thought it would hurt their chances of meeting ‘The One.’

4. Your desire to make money. This might be different for other professions, but for entrepreneurs, money focus can destroy businesses. Money forces you to compromise your values, which should be at the core of great products and company cultures.

A money focus inspires short-sightedness. If you could just do something and ::: BOOM! ::: make money from it, it wouldn’t be that valuable. Entrepreneurs focus on value. Specific, elusive, unseen– it can’t be bought and sold on the open market.

Have you ever spoken to full time investors in financial markets? These are generally people 100% motivated by money. Ask them “if you had a great year, what percentage would you make on your money?” You’ll hear answers ranging from 11 to 20 percent, generally. Now ask the same question to an entrepreneur. 20% would very much be on the low end.

5. Your desire to avoid feeling like an idiot. A month ago I set up a writer’s mastermind group (which has been hugely useful to me). We’ve all tried to address this issue of “feeling stupid” head on. It’s been liberating to post half-baked, ambitious projects in our group chat.

I put a lot of stuff out there, and I suspect most of it doesn’t work. I’m dumb and dangerous, and that’s probably the way it goes for many entrepreneurs. The punchline is that the small percentage of good stuff that sticks around and gets refined, re-worked, and cultivated. One day you wake up with something great. Speaking of dumb, go ahead and download my first 50 podcasts if you want a confidence boost!

6. Your fear of change. I was listening to (a must-listen) Mixergy episode today and Robert made a point. Let’s call it the “paleo theory of fear.” His point: we are wired to fear change. I suppose that’s because back in the good old days, when things changed, you died. Now, not so much. Learning how to both enjoy and engineer change is the foundation of business success. I’ve found that over the years the idea of re-working everything becomes more thrilling and I seek change out.

7. What you are doing right now. Something popped out of my mouth the other day as my good friend (and US expat tax guy) David McKeegan was interviewing me for his podcast. He was asking me about hiring and said “why do business owners find it so difficult to relinquish control and let other people run their business?”

My response got us laughing: “they aren’t having a hard time relinquishing control, they are having a hard time finding something better to do.”

9 times out of 10 that’s true. It’s one of the things I love about creative pursuits in general– you are always at square one. You are always in danger of utter failure. Where you play, there isn’t any sure thing. Read this book and watch a software legend bomb. Listen to John Mayer talk about how songwriting is a great equalizer.

It’s the same with writing and entrepreneurship. Falling back on your cash flows is the same thing as falling back on a job. Often I’ll fail, but I’m always looking for ways to move on and find something more important to do. Hopefully I can backfill the space I create with processes and team members.

8. Your self-focus. Or: putting your immediate needs in front of the principle or the project.  This is the part of the post where I diverge from the hoards of broke-ass personal development bloggers telling you to express yourself more fully or follow passion and stuff like that. Yes, I’m all about that. But we are talking about being Samurai’s here– it’s tough to stay focused on meaningful projects when our passion for Youtube lurks! Entrepreneurship is a strange mix of personal drive and egoless ear-to-the-ground care. It’s a dichotomy I’m fascinated by.

9. Following the advice of others. Have I ever ever mentioned the sharks or the dolphins thing on this blog? Sharks and dolphins are two different types of entrepreneurs. There’s a lot of things that distinguish them. Here’s one: dolphins listen to advice, sharks watch it. Be a shark. Or rather, watch me to tell you to be a shark.

10. Your desire to avoid conflict. For all the kumbaya talk in the blogosphere, you’ll notice that when you meet-up with some of your favorite peace, love, and change bloggers that they’ve got some teeth. I’ve met some of the kindest online personas (and most popular) on the planet, and despite what you see online, they are very often the object of controversy, conflict, extortion attempts, petty attacks, and outright jealousy.

Get in line. It’s par for the course. Asserting yourself in the world means you’ll have detractors. Some of them might even be those closest to you. It’s okay. I try to be thankful for the attention in the first place, pick the places I ought to improve, and try to understand precisely which elements of the feedback are about my projects and which are really a reflection of their own ideas about themselves.

That’s it. I’d be grateful to hear yours.




PS, if you liked this article you can follow my nacent comedy career on Twitter.

Want a download link to my first 50 podcast episodes? I’ll automatically send you the URL if you put your name into the form below:

Published on 05.08.12
  • Good article but I don’t agree with number 4.

    I think good business ideas are lost through lack of focus on profit, after all, without it there is no business. If entrepreneurs focused more on the profit side of their business then there would be far fewer small businesses folding within the first year.

    If I don’t make enough money to live on then I am back in the rat-race.

  • “…and what is really a reflection of their own ideas about themselves.” Yup, that’s true

    #9 puzzles me though, Dan. Not listen to advice? Dolphins? Huh? Please elaborate.

  • One your best articles yet Dan :). Point #8 was a really interesting one. Greg Hartle and I were having a discussion about how short sightedness about money can be a really destroyer of long term value. I think we also live in this world where it’s easy to get caught up in the success of other people since we’re so transparent about what we do online. While it’s good to have role models and mentors, I think you have to silence the noise. I saw this commercial yesterday about a new car where they were saying “on your road the top top plenty of people will offer you advice on something they have no experience with.” It was kind of a silly ad, but it was an interesting point.

  • Nice read, but disagree on point 4 wholeheartedly. I’m actually planning on earning money from my business from the get go, as opposed to taking a “Field of Dreams” approach. How? By filling in a demand right out of the start gate, that happens to be something I believe is great value. Win-win.

  • The sharks / dolphins thing made me confused… or something. I didn’t get it.

  • Heather Thorkelson

    Absolutely loved this one, Dan. It totally resonated with me. A nice divergence from the usual spiel we hear about entrepreneurship.

  • Awesome post as always Dan!
    I like the dolphin and shark analogy and agree with all your points. Especially #6, I’ve always had trouble getting over the fear of change in life.

  • 00sapper

    Needed this one today. Currently going through a little pity party after having some bombs drop in reference to point #2. Found myself wishing people would reach out to those who have a positive effect on them versus taking them for granted. Hence my post to you.

    Very much appreciate your efforts and they don’t go unnoticed…

  • travel_abstract

    I definitely enjoyed this article and it inspired me to write one for my niche. Check for the trackback.

    I don’t quite grasp the dolphin-shark metaphor but the rest is pretty damn useful.

    Even among entrepreneur’s you all measure success differently. It’s about perfecting your focus and defining your own success, quantitative and/or qualitative, it’s up to you.

    Number 10 is a good point for web based entrepreneurs.

    The internet has personas much like television. Rarely are these “personas” the way a person acts 100% in real life. They are part of the person, more importantly a part of the business, but they are not what entirely compose the entrepreneur behind the business.

  • Sheyi

    Great read here. Dan, I guess its true that those that does not outsource are finding it hard to do better things because i wonder what a CEO is doing with designing his website or changing fonts when he can get someone to do it faster and cheaper.

    About making money, yeah, as a ‘trp you should not think about the money side now but the fulfilment that you are doing what you like!


  • I’m not sure I 100% agree with #4 either. I see what you are saying about value, but the drive to make money is what brought me to this mentality in the first place. In fact, moving past the drive and into an actual need is what kicked my ass into gear after hanging out too much with the kumbayapreneurs.

    There is something about value though. And honestly, the money I’ve made has come FROM the fact that I can do something of value. So ideally, maybe the hybrid of this point for me is get rid of the desire to make money from anything that doesn’t bring value.

    And I’m with Johan…didn’t get the shark/dolphin thing. Still…SHARKS FTW!

  • Sorry, I am a little slow on the uptake, as we all know.

    I don’t follow the shark analogy?


  • Agree with Srini, this is one of your best. Your candor in #3 is admirable, that is a struggle I have a bit as well. That any notions we had of what life “would be” probably won’t be. That isn’t necessarily good or bad, really it just IS. The sun still rises and falls on us as long as we’re up and breathing, doesn’t matter what we’re doing or who it is with. They say with any great risk or change it’s like a piece of you might die – for me, it did. The vision of what life “would be” died, I had to put what I thought were my plans for the future in a cold hole in the ground. I wouldn’t go back and slide into that life now, but going through the process felt like a slow shanking.

    Also agree…you need a post on Sharks and Dolphins after the relative glossing of #9. :)

  • Dan, I am a loyal follower of you and Ian and your podcasts.
    This is my first time writing a comment on your blog, and I feel ashamed.

    I must comment to this blog post because it hits me pretty hard.

    I started a local business last year after I graduated from university. I turned myself into a self-employed hustler. Lately I began to feel frustrated with the stuff I do.

    After listening to your “hustler vs. entrepreneur” LBP podcast, I now understand the reasons for my stress and frustration.

    This post totally changes my perspective on what it really means to be a entrepreneur: giving up the things that are holding me back…

    Many thanks, you rock!!

  • Number one thing you have to give up (and probably the hardest):

    On a different note, a business professor once told me that Great White Sharks have to always be swimming to breath. In business you must keep moving forward to survive. Be a Shark.

  • Dan

    Thanks Srini appreciate the kind words! I totally agree about the online thing. You are constantly thrust into the position where comparison is so easy. I’m actively working to stop this kind of thinking. I heard somebody today call it “poison” and that’s exactly what it is.

  • Dan

    Hey David, I probably could have said it better in retrospect. I 100% support making money right out of the gate. Good luck with the biz!

  • Dan

    Yeah it puzzels me too. I’ve always said “there’s two kinds of entrepreneurs” and you can either say somebody is a dolphin or a shark. Never took it any further. LAZY. I’m on it.

  • Dan

    Hey Anthony. The feedback I’ve received on the article has caused me to go back on my thinking here. I think I’ve got a point, but it certainly wasn’t to say that you shouldn’t focus on profit, and that’s absolutely what I said above. I gotta get clearer on that point. The implication that we shouldn’t focus on driving profit is lame.

  • Dan

    Ronnie thanks for sharing that! I’m adding that to my nascent Sharks/Dolphins metaphor! :D

  • Dan

    Ronald, no shame in no comments man! Appreciate you stopping by and taking the time to say hello. Really appreciate the kind words and wish you the best with your biznass.

  • Dan

    Thanks! These ways of seeing our personal life seem to be similar to (and a little more natural) on the entrepreneurship side. We aren’t going to build businesses like we saw in the textbooks, so we need to jettison a lot of those inherited notions.

    Yeah, that was a straight gloss. Gotta get on it. :)

  • Dan

    Nah. I’m right there with ya.

  • Dan

    Yes, I think you’ve found part of the nuance I’ve missed here. Entrepreneurs need to be very good at “making” money, protecting it, identifying it, etc, but the ones who only look for it aren’t looking far enough ahead to be effective. All the guys I know who “chase money” seem to be broke. Whats up with that? There’s something there. Ian and I are very focused on making money, but we are always looking at value first. So this is a whole blog post podcast at least.

    Yeah totally agree on the sharks/dolphins things. I have no idea what it means, but sharks for the win! :D !!!

  • Dan

    Thanks Sheyi… perhaps the biggest small biz problem I see is people got something going (maybe by accident?) and they are having trouble doing the next thing. This is probably related to the problem outlined in Gerber’s e-myth. Most entrepreneurs actually get started as practitioners, so in order to grow they need to learn the skills of entrepreneurship.

  • Dan

    hey I don’t think i saw it yet. If you do write one post the link here!!! thanks for stopping by.

  • Dan

    cheers and thanks for the encouragement. I totally understand that jam! speaking of changing reactions to conflict, check out this recent EP of Mixergy. Really helped my thinking regarding navigating challenging situations:


  • Dan

    yeah buddy, you are in good company :)

  • Dan

    hey Heather thanks for that! Today I’m back on task with the spiel ;)

  • Dan

    haha, nah that’s me being a lazy writer. I have to think that one through. Thanks for stopping by Christina.

  • Pingback: 10 Things You Should Give Up for Free TravelThe Travel Abstract()

  • Pingback: 17 Things You Should Give Up in Order to Be Agile()

  • Here’s the thing with #3 – if you follow the cultural script, you’ll just end up meeting/dating people who tend to believe whole-heartedly in it (and may not be very open to taking alternative paths).

    Whereas if you take the “weird expat path,” you’re more likely to meet interesting women who also share your values. There might be fewer wife candidates, but they’ll be ones who are on the same wavelength!

    (this comment brought to you by personal experience)

  • Dan

    haha appreciate that Shayna. It’s a tough one to believe in, but I think you are right. Couldn’t be happier with how all of my relationships have improved after I started living the way I wanted to.

  • Great article! I realized during the reading that I’ve given up all that stuff in my last 3 years of being an entrepreneur.

Next post: