27 Things I’ve Learned About Business in 27 Years

By Sean Ogle •  Updated: 04/03/12 •  14 min read

Tomorrow is my 27th birthday.

Don’t tell me I’m getting old, because as far as I’m concerned, that still falls squarely in the category of “mid-twenties”.

In that time I’ve made my fair share of mistakes, as well as had a bunch of triumphs.  While these birthday posts can be a bit cliche, I always like reading them, so I figured I’d share with you 27 things I’ve learned about business and location independence over the last 27 years.

1) Theory means very little

Until you have a frame of reference in which to put something in to practice, theory doesn’t mean a whole lot.  This is the major problem I have with people getting MBAs directly after their undergrad (as a few people I know did).  Without the real world experience, you aren’t going to get much benefit – even with the experience the tangible benefit is questionable.

If you’re going to invest the time to learn something, make sure you have a way to apply the theory you’ve learned, otherwise it won’t be worth your time.

2) Uncertainty terrifies most people

As I mentioned in my TEDxCMU talk, there is only one fear in the world: uncertainty.  It’s the root of all fear, and most people never overcome it.  It’s easier to be comfortable than it is to take a risk.  However if you can embrace uncertainty and treat it as the incredible gift it is, the options and opportunities are limitless.

Most people will choose unhappiness over uncertainty – Tim Ferriss

Don’t be like most people.

3) The worst case scenario (almost) never happens

When was the last time the absolute worst case scenario of anything happened.  Sure there’s anomalies, but far and wide it’s when I’m faced with tough decisions that terrify me, that I usually get the most benefit.

My most terrifying experience? Quit my job and move to Thailand. Look where that got me.

When you’re motivated to make positive things happen, they usually do.

4) There’s nothing wrong with a day job

So often people give me shit for talking down about those who have normal day jobs or 9 to 5’s.  There’s absolutely nothing wrong with that. At all. In fact, I think for many people it’s a fantastic thing.

The only thing I have a problem with is people who are severely unhappy doing it.  If you’re not happy then make a change.  That’s all I’m advocating here. If you aren’t able to do the stuff you love on a regular basis, then something is wrong and needs to be addressed.

If your day job is making you happy and fulfilled, then that’s awesome, you don’t need me to tell you what to do.

5) House painting is a fantastic way to learn about business

To this day one of the best learning experiences I’ve ever had was owning my own house painting business. If you’re in college, or know someone who is I highly encourage you to pursue starting a house painting business.  Why? Remember lesson #1 about theory?  This gives you the opportunity to take everything you learn in school and apply it in a tangible way.

So what does this job end up looking like? You learn real world business skills (management, marketing, accounting), get to work outside, make your own hours, and you’ll make way more than the typical college kid will.  Man I need to create an ebook about how to do this…

6) Everyone has something to offer

It doesn’t matter who you are or what your background is, you have something to offer the world.  You’re a relative expert at something, and if you want to harness that unique knowledge, there’s a way to profit off it whether you realize it or not. Don’t waste your gifts, and think hard about how you can harness that to help someone else.

7) Your true self will come out eventually (so don’t hide it)

I know a lot of people online who are totally different from who they are in person.  If there’s one thing I try and pride myself on, it’s that if you meet me in person, you’ll say “hmmm, he’s exactly like I thought he’d be.”  It’s that uniqueness in yourself that is going to set you apart and allow you to be successful. Hide that, or try and be something that you’re not, and it will come out eventually, so why do it in the first place.  Embrace who you are and you’ll be amazed at how much easier things become.

8) There’s always more to learn

I mentioned it in my post about inquiring minds, up until recently I’d never been the most voracious learner out there.  I never consumed books en masse.  Bottom line, there’s always more to learn, and as an entrepreneur, there’s never an excuse for not trying to be better at what it is you do.  I’ve read more books in the last 3 months than I’d read in the last 3 years combined, and it’s amazing how much more success and confidence I have for it.

Go read something, now.

9) Books are more valuable than you realize

Recently I’ve read Influence, The Ultimate Webinar Marketing Guide, and Cashvertising.  You want to talk about an education that will actually help you make money, those books were more valuable than anything I read in college.

Books are cheap (if not free), go get one, educate yourself.

10) Change is scary – being static is scarier

Yeah, making a major life change is scary as hell.  Not making that change, doing the same thing from here to eternity, is much, much scarier.  Think about the most grandiose goals you have for yourself.  I’m willing to bet that if you want to accomplish most of them you’re going to need to make a big change in your life.  I certainly had to.

It goes back to the fear of uncertainty. It’s terrifying, and even worse than that its debilitating.  However, if you want to reach your full potential, you need to make that change.

Don’t run away from it.  Embrace the change and thank me in a year.

11) Business should be fun

If you’re in business and don’t like what you’re doing, something is wrong.  That’s the best part about being an entrepreneur.  Getting to wake up every day and do something you’re passionate about.  Something that makes a difference.  Something that you’re proud of.  If you aren’t feeling those things on a daily basis, it’s time to reassess what you’re doing.

Sure there may be aspects of business that aren’t your favorite, but those should be a small fraction of your daily activities (assuming you can’t outsource it completely).  Build something that makes your life enjoyable.

12) “Everyone” is not a target audience

I was talking with Peter Shallard this morning, and he mentioned that with one of his businesses he wanted to create something that appealed to .001% of all internet users.  If you can do that, and do it well, you can have a wildly successful and profitable business.

As soon as you try to appeal to everyone, warning sirens should be going off in your head.  If your business is too broad you won’t appeal to your core market on a deep enough level to bring them on board – effectively shooting yourself in the foot from the beginning.

Create a detailed customer avatar or profile before you start doing any marketing, and keep it in mind in everything you do.  You and your bank account will be glad you did.

13) A blog is one of the best ways to grow any business

I said it in early 2010, and I’ll say it again now: if you want to become a lifestyle entrepreneur, start a blog.  It’s the absolute best decision you’ll ever make, period.

14) Form your own conclusions

Everyone is going to have their own opinions about your business and how you should run it.  Listen to what others have to say, but don’t take anything as gospel.  You know your life, business, and market better than anyone, so trust your gut and instincts more than any external force.   When you place more trust in someone else than yourself you risk jeopardizing everything you’ve worked to create.

15) Starting a business isn’t hard – continuing it is

I’m fantastic at starting things.  I can take an idea, get people excited and get things off the ground, but when it comes to getting past that point, I struggle.  Anyone can start a business, however it’s those who can take things a step farther than that see things through that are going to reap all the rewards of business ownership.

When I started Location180 I really wasn’t sure I’d be able to stick with it.  I thought it would be like so many other things I’ve started that have fallen by the wayside.  It’s one of the greatest accomplishments in my life to be at 295 posts and counting.  It’s an incredible feeling and to think about how far I’ve come is truly humbling.

16) You already know what to do

There are millions of people out there looking for the answers to whatever problem they’re facing. The reality? You know the answer. If you wanted to start a successful blog or business, there are thousands of free resources out there on how to do it.  I’m willing to bet that deep down you already know what to do. Knowledge isn’t the problem – motivation is.  Most people don’t have a deep enough motivation to make things happen.

This is the reason why info-products work so well.  Do any of them have incredible revolutionary information? No.  But when you pay for something, you’re holding yourself accountable for actually doing something with the information your given.

You already know what to do, now just figure out what is going to motivate you to take action.

17) Say “yes” more

I’ve recently been struggling with whether or not to take a trip to China and Hong Kong for some potential business opportunities. The short term cost is fairly high, but the long term potential is huge.  I’ve realized that I’d regret not going and having the experience, much more than I would regret going and getting to do some cool stuff in the process.

If unique opportunities come your way, say yes.  Chances are you’ll be glad you did.

18) Say “no” More

In direct contrast to the advice above, you also need to be willing to say no more as well.  As your business grows you’re going to have no shortage of things to keep you busy and invest your time in.  Choose your projects carefully, and weed out the things that aren’t exciting, draining, or don’t fall in line with the core goals you’ve set for yourself.

In short say yes more to things that excite you, say no to everything else.

19) Positive habits are essential

It doesn’t matter if its setting your work schedule, eating well, getting regular exercise etc.  If you can’t create positive, long term habits for yourself, you’re screwed.  You have to have the energy to make things happen, and without positive habits, over time you’ll get worn down in a way that’s very difficult to recover from.  Never take your physical or mental health for granted.

20) Happiness is everything

If you aren’t happy what’s the point of anything? The people around you won’t be happy, and it will be much more difficult to leave a positive mark on the world.  Do what you have to do to find personal happiness, because it’s finding that for yourself that will allow you to share much greater gifts with the rest of the world.

21) Accept help

It’s easy to let our ego take over and try to deny help when it’s offered.  However by accepting help from others, especially in areas of weakness for you, you’re improving your life greatly in the long run.  You’ll be able to pass on any wisdom and pay forward any assistance you get from others, making everyone better off in the end.

You don’t know everything, you never will. Accept help graciously.

22) Offer Help

This goes back to the idea that you have a unique expertise that you have an obligation to share with the world.  Even if it’s refused, continue to offer help to those that need it.  Whether it’s with your time, your money, or your unique knowledge, give without expecting anything in return, and you’ll end up receiving more than you could ever anticipate.

23) Don’t Forget to Play

It seems that after about the age of 10, most of us forgot how to play.  It’s more important now than ever to take time out of every week to do something fun.  This is a theme that is weaving itself in and out of this post, but the vast majority of the people I talk to are too serious.  They’re drained, and the quickest way to revitalize yourself is to take time out, do something fun with people you love, and get out of your work for a change.

24) Attitude is Everything

If there’s one trait of mine that I would attribute the vast majority of my success to, it’s the fact that I always try and be positive regardless of the situation. I’ve always been a pretty “glass-half-full” kind of person, but it wasn’t until I started building a business that I realized just how important and beneficial this attitude is.

When things are bleak, find the positive.  There always is one, and chances are you’ll come out better on the other side of whatever crap you’re going through.

 25) Nothing has to be perfect. 

If I waited until everything was perfect to put it out in the world, I’d be nowhere.  Sure there’s times that it may not be ideal.  I can guarantee this post will have copy errors in it.  Yet if I waited and spent excess hours trying to achieve perfection, I’d be missing out on many more important opportunities.

This is no excuse to be sloppy and not try, but if something isn’t perfect, don’t beat yourself up, the chances are good that no one really cares.

26) Feeling stuck? Just do something

Doing something, even if it doesn’t end up being the right thing is vastly better than doing nothing at all.  It’s so easy to stay stuck in the same infinite loop of self doubt, pity, and uncertainty.  Anything you can do to break out of that during a low point is good. If you find yourself in a bad place, take note of it, make a change, and another, and another, and eventually you’ll find yourself in a better place.

 27) Stories are worth more than just about anything

That’s what all of this is all about. Stories.  If I don’t have any good stories to tell in 50 years looking back on my life, I must have done something wrong.  I feel fortunate that I’ve created enough of them in the last two years that I feel like I could stop right now and be pretty good, but where’s the fun in that.

Set out to do interesting things, and help everyone you can in the process.  That’s a recipe for a good life in my book.

Birthday Present! 

This year I’m getting a pretty cool birthday present – from a complete stranger.  Tomorrow night I’ll be heading back to Georgia (for the first time since I moved from there when I was six) to attend the annual Masters golf tournament with Location 180 reader Gene Jennings.

He shot me an email months ago after reading on my bucket list that I want to play Augusta National Golf Course. While I won’t playing the course, attending the tournament can easily qualify as bucket list item#27 Part B.  Seems like a perfect fit for my 27th birthday.

If you’ll be in the area be sure to let me know!  It’s been a fantastic 27 years, here’s to 27 more that are even better.

Photo Credit: Steve Wilhelm

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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19 comments on "27 Things I’ve Learned About Business in 27 Years"

  1. Dan says:

    Wow! What a great reader gift! That extra flavor def. makes it qualify for a cross off the bucket list. Sounds like a ton of fun.

  2. Happy B’day, Sean! You sure have made it pretty far in your 27 years! Imagine where you could be at 54! Wowsers ;P

  3. Tom Meitner says:

    Hey, happy birthday Mr. Ogle! Two of my brothers are headed down to the Masters as well – they love it. You’re going to have a blast – and thanks for sharing all the killer information!

    1. Sean says:

      Nice! If they’ve been before and have any words of advice for a first timer, feel free to pass them along.

  4. Liz says:

    What’s really funny is that I was talking to some other LR peeps after the big meet up and they all asked “What’s Sean like in real life?” My response, “Exactly how I thought he would be.” So you’ve got that dead on. Great list, so many of these are tips that I have learned from you, and follow now on a consistent basis.

    1. Sean says:

      Thanks Liz! I think that’s one of the best compliments I could receive 🙂

  5. Happy birthday, and a great list. #2 and #10 hit just about everyone at some time. You get stuck doing something and although you may want to change your afraid of giving up the security. I have made a few changes over the years and for the most part they have all been good. Even the ones that didn’t work out so well I learned a lot and came away with things to help me later.

  6. Élan says:

    Happy birthday! I’m coming out my lurker shell to wish you a very happy birthday, and I hope you have a fantastic time at the tournament.

    This list is fantastic. I love #17 & #18. I’m really trying to say “yes” and “no” to the right things this year.

  7. Jeffrey says:

    There’s so much that you’ve hit dead-on for me on this list. I’ll second Liz’s comment as well on meeting you in real life, Sean. Happy birthday and enjoy the Masters!

  8. Tiffany says:

    Happy Birthday! I hope the golf trip is a blast!

  9. Jason Martin says:

    Awesome post. Lots of wisdom condensed in 27 short years 😉

    And happy birthday eve 😉

  10. Thanks for the shout out. I look forward to being your tour guide to the greatest golf tournament in the world!

  11. Kent says:

    Happy Birthday Sean!

    Great list. I think my favorites are the last three! Bookmarking this for future reference and motivation. Have a blast at the golf tournament.

    P.S. Intentional or not, loved how number 8 turned into an emoticon in my browser.

  12. Untemplater says:

    Happy Birthday Sean! Man I wish I was turning 27 again. But I’m so much happier now and think my life is a lot cooler now than when I was younger so that’s all the matters right? 🙂 Love your list. Have fun at the tournament!

  13. Jamey says:

    I read every post but never comment. Just wanted to comment by saying happy birthday Sean! Keep up the keepin up, whatever that means.

  14. jamey says:

    What’s your handicap? Shot below 80 yet?

  15. Lubo says:

    Amazing post! If there would be only 10 points, it would be awesome, but you could make it full 27. Happy bday and all the best!

  16. Benny says:

    Great lessons in this post. Happy birthday and enjoy the Masters!

  17. Asia says:

    I’m all about #27 – Stories are worth more than just about anything!

    Whether you’re partying in the Philippines or the trailer park, it’s worth the experience if you can come out of it with some good stories.

    I believe that great stories inspire great writing.

    Happy Birthday Sean! I see even more great stories in your future.

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