10 Invaluable Lessons I’ve Learned in 4 Years of Being a Lifestyle Entrepreneur

Yes, you read that right, today Location 180 is 4 years old.

This is unbelievable to me.

No seriously, I have a hard time believing that it’s actually been so long since I wrote that first post, and that I’ve been able to cram so much life into such a short time.

Even in the time since our 2 year anniversary post, things seemed to have really picked up.

This last week I’ve been in Chicago speaking at SOBcon 2013 which has had me reflecting a lot on where I’d like to see the next 4 years ago.

Note – This conference was incredible, if you’re in Portland in the Fall I highly recommend you come check out their West Coast iteration.

Today however, I want to focus on the past. The lessons I’ve learned from Location 180 and this lifestyle have been the most invaluable ones I’ve ever learned. Where college taught me what I thought I needed to know about life, writing this blog and pursuing this lifestyle has given me the lessons that I really need in order to be successful moving forward.

So here it is, Confessions of a Lifestyle Entrepreneur, if you will. These are geared towards people pursuing a lifestyle business, but regardless of who you are you should be able to get some value out of these.

1) Never Stop Selling

It’s easy to get comfortable. Just as you can get comfortable in a day job, you can get too comfortable in your own business as well.

Over the weekend I was talking about this with Scott Jangro, founder of Shareist, . And he mentioned how many businesses he’s seen evaporate overnight for reasons completely beyond the owners control.

In any business it’s easy to think you can just switch to autopilot and the sales, clients, customers, etc. will just keep rolling in.

At some point the well will dry up.  Always be selling – especially when you don’t think you need to.

This is more broadly applicable to life as well. We’re always selling, whether its our thoughts, ideas or our products, the more you do it the better you get. The better you get, the better your ability to influence the world in the way you want to see it changed.

2) Your Platform is Even More Important than You Think

Nearly everything I’ve experienced over the last 4 years has been a result of my platform.

First it was the push out the door from my day job. Then I was offered the Tropical MBA, and work with Chris Guillebeau. From there it’s taken on a life of it’s own that has given me the ability to do more in 4 years than I could have expected to do in 40, had I stayed as an analyst.

When you have a platform online you have a voice, you have leverage, and the more it grows the greater the opportunities become.

Establish your platform now, even if you don’t know where it’s going to lead or what it’s going to be all about in the long run.

Look at my previous blog posts. In the beginning, Location 180 was nothing even close to what it is now – and that’s ok.

With the way the world is evolving, your online platform will become more and more important in your ability to build relationships and do the things you really want to do in life.

3) Meet More People – But Don’t Have an Agenda

The more people I meet the more enriched my life becomes.

As a solopreneur it’s easy to hole up in coffee shops and become a bit of a recluse. I often have to force myself to go out and be social, but when I do, I’m always glad I made the push.

At SOBcon this weekend I met some unbelievable people and entrepreneurs and I did my best to get to know them first, before I found out about what they did.

I hate being the person whose always looking for the angle in a conversation. You know the whole “how can this person help me?”

Nobody likes that person, and we’re all guilty of doing it from time to time, but when you build genuine relationships with no ulterior motives you’ll usually gain more than you expected to in the first place.

Start with the relationship, and only worry about the relationship. You’ll get more out of it that way, I promise.

4) Spend At Least 1 Hour a Day Being Creative

It’s really easy to get caught up in life; the last 4 days I’ve barely cracked my laptop.

However, my livelihood completely depends on my ability to provide value to others. That means being creative, and when I fall out of that mode things can go downhill quickly.

Some people strive to write 1,000 words a day, others spend a focus amount of time on deliberate creation. However you choose to do it, make this a priority.

The more you create, the more opportunity there will be for others to consume, which in turn builds your reputation and makes you money.

During the times when I stick with this, the rest of my life is always better because of it. I get more organized, more focused, and I feel better about the work I’m accomplishing.

5) Do More of What You Want to Do (Selfish Isn’t a Bad Word)

For the last few years of my life, I’ve been incredibly selfish – and I have no problem saying it. I’ve made major changes and choices based on what I want for my life. Is that a bad thing? No way! You’ve gotta look out for #1…but there’s more to it than that.

Help yourself first, then help others.

That’s how I look at it.

Until I was happy with my own life, there was no way I’d be able to help anyone else on a large scale.

It’s because I’ve been selfish that I’ve been able to reach a broad audience and help change the trajectory of a lot of lives.  Don’t feel guilty about doing things for you, because that’s where doing things for others begins.

6) Uncertainty is an Asset

As I mentioned in my TEDx talk “The Future of the American Dream” the majority of the world will always be afraid of uncertainty – and that’s why they will never make the changes necessary to live the life they really want.

Those that embrace uncertainty and recognize that because everything is uncertain, anything is possible, will be the ones who go far and make the biggest difference in the world.

The easiest way I’ve found to get over this problem? Ask yourself the question “what’s the worst that can happen?” and really truly think about the answer.

The reality? The worst case scenario will almost never happen, and it’s usually not as bad as you think.

7) Adventure Regularly

Routine is necessary in life, but it can also drive you crazy.

If I stay in one place or my routine gets too repetitive over the course of a couple weeks, I go crazy.

How do I fix this? Adventure regularly.

Adventure is probably my favorite word in the English language. I can’t say it without conjuring thoughts of Indiana Jones or rope swings through Amazonian jungles over cascading waterfalls – but I digress.

While jungle swings are certainly cool, an adventure can be much more basic than that.

My adventures are the things I remember the most. They’re one of the key reasons why this lifestyle is so worth it.

Go to a new place, meet a new person, do something out of the ordinary. Any of those things can be adventures. Understand routine has it’s place, but don’t be afraid to break it up.

8) There Will Always Be Something You Could Do

As an entrepreneur, there’s always something to do. Always.

You should never be able to say “I’ve got nothing to do.”


Because you’re the heart and soul of your business. You can test, create, sell, meet, share in so many ways its not even funny. If you aren’t doing any of those, then you probably should be.

That being said, once you recognize there’s always stuff you could (or should) be working on, you can consciously make a choice not to do it.

For a long time I’ve wrestled with this. When there’s always something to do, it’s easy to feel guilty when you take time off or skip work to do something fun.

Don’t feel guilty about this. That’s the whole reason why we’ve chosen this lifestyle to begin with!

When you’re working, work hard. When you’re playing, train yourself to let work go and really enjoy what you’re doing. It’s very easy to let work creep into your play time, and that’s not fun for anybody.

And yes, I know there’s a smiley in the heading 🙂

9) Life Doesn’t Suck

I’ve adopted this tagline for myself over the last year or two.

If you’ve spent any time with me, you’ll hear me say it often. Why?

Because it’s true. Sure we all have bad days, but if you take a step back and look at your life and what you have – I’m willing to bet it really doesn’t suck that much, no matter how much you dislike your job 🙂

10) There is No End, So Don’t Dwell On It

If you haven’t realized it yet, there is no end. There is no “making it”. It’s all part of the process and the journey, so stop expecting everything to be different when you finally _____.

No matter how successful you get, or how perfect of a lifestyle you have, you’ll still have problems. Shit will still happen, and a million dollars will not necessarily make you the happiest person on earth.

So how do you deal with this?

Enjoy the ride, that’s what it’s all about anyway.


Seriously, the last 4 years have been unbelievable and the next ones are only going to get better.  This wouldn’t be possible if it wasn’t for your support, so from the very bottom of my heart, thank you so much for helping to make this possible.

Sign up below and shoot me an email if there’s anything I can do to help out with your journey in anyway – after all, freedom’s more fun with friends 🙂

Jovanni G May 8, 2013 at 6:41 am

Thanks for another great post. There was some great value in this post. Information that I can implement on my blog as I try to achieve my lifestyle business.


Dan May 8, 2013 at 7:26 am

Big ups and congrats Sean. We are getting old brother 🙂 Looking forward to the next 4.


Sean May 8, 2013 at 7:30 am

haha ain’t that the truth. I’m looking forward to our paths crossing again sometime soon – been way too long!


Carlo May 8, 2013 at 7:46 am

Congrats on the four year mark Sean. I’ve only been a reader here for a year, but I’ve learned so much from you in that time – so thanks for that alone.


Gunnar May 8, 2013 at 8:08 am

Happy anniversary Sean!

Always great info and insight. I like your comment on building a platform.

What do you think was the tipping point for Location 180, when it started becoming a real catalyst?



Sean May 8, 2013 at 8:18 am

To be honest, I think it was the day I left my job. Because then everything I was just talking about became real. If I didnt have the guts to actually take action on the stuff I’m writing about, no one would be interested.


Leigh May 8, 2013 at 8:10 am

I’m so glad I discovered this website at the beginning of this year. You’re articles have taught me so much about lifestyle entrepreneurship and I’m looking forward to my own journey into it!


Sean May 8, 2013 at 8:19 am

Thanks Leigh! Glad I could help, if even a little bit 🙂


Nate May 8, 2013 at 8:25 am

Congrats on 4 great years my friend! I remember reading your site when it first started, way before you even left your job. I’m a Location180 hipster.


Sean May 8, 2013 at 8:30 am

I should make t shirts for that haha. Goes both ways though, I remember when you didnt have hair!


Carlo May 8, 2013 at 9:05 am

Location 180 and Location Rebel T-shirts ftw!!! 🙂

Molly May 8, 2013 at 8:43 am

I’m in the middle of a move to Chicago. Literally in limbo, crashing on a friend’s spare bed while my worldly possessions wait for the U-Haul in her barn. Yesterday, I went to go say goodbye to my daughter, who is finishing her senior year at college.

While waiting for her, I was reading an essay about The Abyss in Poetry Foundation magazine. I realized that even though I WAS in the abyss right then, I was also cradled and surrounded by beauty. It was a clear, sunny, bug-free, humidity free spring day on the Ped Mall. I had a great glass of white wine, a stomach full of sushi and the capacity to appreciate it all.

My life has some serious obstacles, but there are such moments of grace that encourage me to move forward. Thanks so much for a great post. Best, M.


Lily Gavi Derrick May 8, 2013 at 8:54 am

Thanks for this post it is exactly what I needed. I’m getting ready to leava a job to build my business.


Jean Powell May 8, 2013 at 9:30 am

You are my continual rockstar hero.


Jason Moore May 8, 2013 at 10:00 am

Sean, huge congrats. I refer back to many of your posts quite often as they are always packed with value which helps to provide both ideas and solutions for my businesses. Keep up the good work and hope to see you in Colorado at some point.


Jeffrey Trull May 8, 2013 at 10:42 am

Congrats, Sean! I’m really glad to have come along on most of this journey with ya.

Thanks to you, life doesn’t suck for a lot of us!


Gaël May 8, 2013 at 11:04 am

You had me at “adventure” 🙂

Great post otherwise Sean! And congrats on the 4 years! Looking forward to hear more of your travels 😀


Steve Woodruff May 8, 2013 at 3:56 pm

We were very glad to have you at SOBCon, Sean-it was a real pleasure brainstorming with you!


Sergio May 9, 2013 at 9:04 am

Congratulations, Sean! May the years ahead be more awesome!

I’m glad I get to know of you by your articles. You have always something to give us that we can use to progress as well.

That’s what matters.

Hope someday we can catch up somewhere. Cheers!


Brooks May 11, 2013 at 8:42 am

Yes. Yes. Yes.

This list is so REAL. It’s Legit.

I work for myself and I constantly struggle with the ”I should be doing…” mindset. After 4 years, I also still struggle with normal working hours. Although I’m productive in the early morning and also late at night, I struggle in the afternoons with my mindset. Although I take park walks and other breaks on pretty days, I constantly struggle because I feel like I should be working. Everyone else is at work, so shouldn’t I be?

But as you stated, as entrepreneurs, we can ALWAYS be doing something. So thanks for the reminder to take time, to be creative, to be young, to go explore.


Brooks May 23, 2013 at 9:44 pm

Man, I just came back and read this post again tonight – great stuff.
And yes, it’s late at night – close to midnight (one of my productive times)


Carrie May 12, 2013 at 5:14 pm

Congrats on hitting the four-year mark Sean! It’s such an awesome accomplishment and something I personally appreciate as reading your story is not only practical but inspiring! I can’t wait to see what the next four years have in store. Cheers!


Lise Carter May 12, 2013 at 5:24 pm

Awesome! That’s all there is to say about this achievement! I’m coming up to my 1 year anniversary of quitting my job and it’s all thanks to you and Location Rebel!!

Thanks for doing what you do Sean, it makes a difference 🙂

I can’t wait to reach the 4 year mark and look back on how awesome those years have been too!!

Take care


Matthew Trinetti May 12, 2013 at 7:42 pm

Congrats Sean. Keep on inspiring and showing us the path.

Your honesty is refreshing (ie: “it’s easy to feel guilty when you take time off or skip work to do something fun;” “In the beginning, Location 180 was nothing even close to what it is now”). It gives me strength & confidence to keep going. Keep it up!


Gene Jennings May 13, 2013 at 4:42 am

Congratulations Sean! Good stuff. You’ve got 10 bullet points for another speech or eBook.


Bill Barlow May 13, 2013 at 7:11 am


Congrats on 4 years! I’ve been following you for about 9 months now and it sure seems you’ve worked hard for it. You are a real inspiration to those of us attempting to achieve what you have. Keep up the good word and the great posts!



Chas May 14, 2013 at 6:54 pm

Some great thoughts. Thanks for swinging over the fences.


Liz May 15, 2013 at 10:59 am

Keep rockin’ Sean 🙂


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