10 Things I’ve Learned in the Three Years Since Leaving My Job

Last week I realized that it had been three years exactly since I left my job.

It’s terrifying how quickly these three years have gone by, but at the same time I’ve crammed a lot of cool stuff into these three years.

The short list including:

This list is just the tip of the iceberg, and words cannot describe how thankful I am for every single one of these experiences.

This post was originally going to be titled “10 Coolest Experiences I’ve Had Since Leaving My Job”.

Then I got an email from a reader who unsubscribed and said he felt the site was too much about me, and not enough about the goals of my readers.

While this site is about me, my life, my business and my journey, the goal is to still make it a valuable tool for others looking to build a business.  I’ll devote a few posts at the end of the year to my personal progress, but after thinking more about it, I realized aside from maybe serving as a bit of motivation to go do something cool, the only thing that post would have been really serving was my ego.

Let’s be real, I still included that list above, part of that was patting myself on the back.

But ok, enough of that.

I wanted to rewrite the post in a way that might actually give you something to think about.

So instead of bragging about where I’ve been and what I’ve done, instead I wanted to share with you the top 10 things I’ve learned about entrepreneurship since leaving my job.

In my experience if even one of these 10 things resonates with you, it will be worth the 2 minutes you spent to read the post!

1) Nothing Will Ever Go Fully According to Plan

Sometimes the detour from the plan will be so vast you’ll wonder how you’ve gotten to that point and if it’s possible for things to get any worse.  Other times things will go even better than you could have imagined.

Either way, it will all work out.  When I relaunched Location Rebel last September you wouldn’t believe how many things broke.  I had to hop a flight to Asia and none of the forums we’d spent over 6 weeks cultivating worked.  The affiliate system didn’t work.  Every time I fixed one of those two things, the other would get even worse.

Bottom line, it’s all just a distant memory.

In thinking of every single thing I’ve ever stressed and freaked out over, it’s all just a memory.  At this point, in this moment, I’m totally fine.

No matter how far off plan things go, everything will be fine.

2) There’s Always Another Way

Something not working? Not happy with the way your life is going? Can’t figure out how to get that golf ball over the tree?

There’s always another way.

One of the most valuable lessons I’ve learned in entrepreneurship is that if you’re beating yourself up over something not working, take a step back and think about it in a different way.

Are your strategies for getting traffic not yielding results? Not sure why your sales page isn’t converting? Can’t figure out why no one retweets your Twitter posts?

Do something else, there’s always another way to achieve the same goal.

3) An Unending Sense of Urgency Is Necessary to Succeed

As soon as you set yourself to cruise control you’re screwed.

So many people are after the elusive dream of passive income.

What you may not realize is once you get there, the work just gets that much harder.

I know people who have built incredible passive income streams – easily making five figures per month.

Then  you know what happened? The got complacent.  The sense of urgency was gone.  Customer service went to hell, product updates were non-existent, and the follow up product? Nowhere to be seen.

It’s easy to say hey “I’ve got passive income! Wooohooo! Time to retire.”

The reality however is that so much can change over night.

Most people do their best work when their back is against the wall.  If you’re anything like me, you did way more studying the night before a big test than any other time.  It’s because you had to.  There was no more time to procrastinate.

It can be easy to settle in and get comfortable as soon as you’re making enough to live on.

Don’t let that happen. Continue to build, create, and innovate all while living that “retirement lifestyle”.

4) It Doesn’t Matter How Hard You Work

We’ve all heard the old adage you have to “work smarter, not harder”.

Well it’s completely true.

No matter what you’ll be able to find work to fill your time.  You could easily spend 12 hours a day working on all sorts of stuff in your business.  But if it’s the wrong stuff, all you’re doing is wasting time.

To be honest, my most productive and fulfilling days are usually the ones where I spend less than 4 hours at my computer.  If I spend over 6 either I’m leading up to a big project or I’m doing something wrong.

I’ll find stuff to keep myself occupied for as long as I’m sitting at a computer, that’s why it’s so important to get away from the computer as often as possible.

Each day make your to do list.  Then go back and look at each item and ask yourself “is this adding to the bottom line of my business?” If not, then consider if it’s really an essential task for the day.

You should always know why you’re working on something.  As soon as you’re doing work for works sake, you not only will be hurting your business, but that’s when self-doubt and unhappiness set in as well.

5) You’re Always Selling Something

Literally, always.

An idea, a concept, a product, you, your services – you’re always trying to persuade people to think a certain way about something.  Maybe it’s as simple as getting them to like you or something as extreme as selling them a high priced product, but you as soon as you become aware of this reality, you can use it to your advantage.

I’m not talking about turning into a sleazy salesperson with everything you do – rather, educating yourself on principles of psychology, copywriting, and becoming more deliberate with your actions.

Learn how to communicate effectively through as many mediums as possible.  The world is changing and you can use each of those channels to help build your business and brand.

6) You Have to Have a “Why”

Why become an entrepreneur? Why take the risk? Why go through the stress and hardship of building a business?

If you don’t have a why you shouldn’t be doing it.  I talk to a lot of people who can’t answer that question.  They don’t like their job, and this seems like the next best thing.  Those people should be getting a different job, not creating one for theselves.

For me the why is two fold:

  • Give myself the ability to do all the cool stuff I’ve always wanted
  • Help others achieve the same thing by helping them build small businesses
I couldn’t ask for more.  To do everything I want, while getting the privilege of helping others do the same is incredible.

7) A Solid Community is More Important Than You Think

Back when I had my day job, I used to talk to my best friend Ryan every day during my lunch break.  At the time he was living on Maui and I was wearing a suit and tie.

The support I received from him, as well as the quickly growing Location 180 community gave me all the motivation I needed to start making some major changes to my life.

Without that support I’m not sure I would have ever left.

If you want to make drastic changes or grow a business you need consistent exposure to others who are working on the exact same thing.  The people around you rub off more than you think.  If everyone you’re spending time with is talking about getting that promotion to middle management or their vacation to Hawaii at the end of next year – you’ll eventually adopt the same mindset.

Seek out people doing what you want to do, and spend as much time as possible with them.

8) You Can Learn Anything, Quickly, If There’s Enough Motivation

Note: Yes I know there’s a smiley above, go with it!

Most of us grew up in a very traditional education system; one in which it took 16 years to become “educated”.

With the internet, and the incredible amount of high quality, specialized information readily available you can learn just about anything in weeks, not months or years.

Whether it’s learning the basics of WordPress, how to ceate a memberbership site, or how to properly do SEO – you name it, you can learn it.

As an entrepreneur, there’s going to be a ton of stuff you don’t know how to do, but you better believe you’ll need to learn it.  You can’t afford to not learn it quickly.  You’ve gotta be on top of your game, adapt, and move onto the next thing.

However if you really want to rapidly build skills you’ll have to learn from some of the other lessons: have a sense of urgency, surround yourself with the right people, and know why you’re doing it.

9) Play is Essential for Work

A trend I’ve noticed over my three years of self-employment is that the more I play, the greater the desire is to work.

If I have an extended period of time where all I do is work, I tend to forget why I’m even working.  When I’m off having adventures or doing something fun I almost always come back yearning to work.  I’m always the most productive and enjoy my work the most immediately after doing something fun.

By playing on a regular basis, I remain motivated to work.

It also serves as a reminder as to why I chose the path of lifestyle entrepreneurship as opposed to a traditional job or startup path.

Sure I may never sell to Facebook for a billion dollars – but on the other hand, who knows.

No matter how much you think you always need to work – you don’t. Life is short, remember to have fun.

#10) It Never Gets Any Less Awesome

I’ve referenced this multiple times over the last three years.

Right after I left my job and started working with the Tropical MBA crew, Dan Andrews told me something I’ll never forget. He said:

“No matter how many years pass, it never gets any less awesome,” referring to being a lifestyle entrepreneur.

And you know what? He was absolutely right.

I love my life.  I love helping others with their lifestyle goals, traveling the world, and having the flexibility and freedom of time.

Being an entrepreneur is incredibly hard, and it requires a complete departure from what you’re used to in a traditional job.  But if you think you have it in you and you think it’s right for you, by all means give it a shot.

The rewards are apparent each and every day.

What’s the ONE most important thing you’ve learned about entrepreneurship? 

Financial Samurai October 30, 2012 at 9:41 am

Hey Sean!

It’s great you took the person who unsubscribed’s feedback to heart.

What do you think a good balance is between selling yourself and helping readers on your blog? How important is ego, or a lack of ego to be successful online?




Sean October 30, 2012 at 9:54 am

The way I look at it, is this site is still all about my journey, and the goal is to help as many as people as possible via my experiences. I’m still going to write about my life in an honest and transparent way, and more often than not write about strategies for helping others build a business.

While I don’t necessarily agree with that person that I focus on myself too much, I do realize where there’s times I could be more useful and/or not write things that just boost me up.

You have to have confidence in what you do to be successful online, also I big part of my marketing is the fact I’m going out and doing cool stuff on a regular basis – that said, there’s a balance between all of it, and you try and strike that as much as possible.


Craig Anthony October 30, 2012 at 9:56 am

One of the most important things is to deeply believe in yourself and what you’re doing.

When you break off from the usual routine and start heading towards what you really want to do, so many people are going to be negative and give you crap about it.

Learning to ignore the naysayers and not them affect you is key. Doubt in yourself will cause a huge derailment.



Shayna October 30, 2012 at 10:43 am

These are super valuable lessons. I love hearing from people who are farther ahead in the process than me (I’m at 10 months) yet who are not so advanced that they’re completely out of touch with those of us who are just starting out!

My #1 thing – Do it like a scientist.

Iterate, adapt, test, keep what works, scrap what doesn’t, keep moving forward and constantly improving based on feedback from mentors, customers, leads, etc.

Note: By “testing” I do not mean that beginning entrepreneurs should mess with their button colors and header design and other such A/B testing tweaks. In my opinion, you need to nail the product/market fit and prove the fact that people are willing to pay for what you’re offering before starting to optimize those little details.

Oh, and keep your emotions the heck out of it. That is to say – of course you’ve gotta have the driving passion behind it, the big “why” like you described. However, the journey has so many ups and downs that you can’t let the fluctuations dictate your emotional health or motivation to keep going.

Product launch a miserable failure? Don’t cry about it and slack off or give up – ask what went wrong and do the next one better. My first attempt got a whopping 3 customers. When I look back on it, the product and presentation were pretty terrible, but it got me way more upset than it should have at the time. But I tried to step it up – and the next product got 12 buyers, the third product got 20, and now I’m at 45.

I kind of wish I’d kept a log of the approximately 500 iterations I’ve gone through as my business concept/model has evolved!


Scott Nelson October 30, 2012 at 11:47 am

I totally agree Shayna. I’m just coming to the end of a book called ‘the lean start-up’ and it’s all about testing quickly and cheaply (although a slightly dry read). I’m definitely guilty of not recording everything I do though. I’m starting to get better though; I set monthly reminders to record my visits and sales and then usually put a note retrospectively on any changes I’ve made during that period.

I think over time people develop a gut instinct on what works and what doesn’t work, but this instinct would almost definitely be honed more quickly if we kept a change log!

Sean, long time follower, first time poster. Personally I feel the more you post about yourself and what you get up to, the more unobtainable it seems. If you drop hints of how you’ve achieved your location independant lifestyle, I’m more likely to a) believe in myself and b) believe in your product and your brand. Hope this helps.


Sean October 30, 2012 at 8:30 pm

Scott, this is actually really useful for me to hear. I appreciate the honesty, and I’ll take that to heart as I’m planning my marketing and posts that are coming up.

Sean October 30, 2012 at 8:31 pm

I love it! I’ve never thought of the scientist analogy, but it makes so much sense – a great way to look at it.


Maurice Lindsay October 30, 2012 at 3:48 pm

Great post, love the way you keep it 100% real man. Out of all 10, #1 and #3 are my favorites. Nothing will ever go according to plan no matter how much we plan it. The important thing is to always be prepared for the unexpected. And a sense of urgency is always needed for us solopreneurs. You have to stay hungry and want it just as bad as the first day you started the journey. The sooner you lose your hunger, the sooner things can all go bad, and end you up back in the workforce.


Sean October 30, 2012 at 8:29 pm

Couldn’t agree more! Appreciate the thoughts


Dan October 30, 2012 at 5:48 pm

Congrats on 3 years man!!! Wow time flies. FYI… I can confirm for the sake of science… it’s still getting better 😀


Michael Ten October 30, 2012 at 9:27 pm

Inspiring post! I can imagine being location independent would always be extremely satisfying!


Janet October 30, 2012 at 10:27 pm

I remember 3 years ago too, for you and me, and yeah.. time flies. WOW! You’ve accomplished a lot. Congrats!!


K. Robinson October 31, 2012 at 4:45 am

I really can relate to the lessons you listed, especially “You Can Learn Anything, Quickly, If There’s Enough Motivation.” Currently learning/teaching myself Korean to take a proficiency exam. It’s paid off in dividends as I can better relate to my neighbors and students (I’m an English teacher in Korea). Great read. Cheers!


Katie Leimkuehler October 31, 2012 at 10:10 am

This is an absolutely great list Sean! Thanks so much for sharing it. I think it really gives aspiring entrepreneurs motivation and energy to keep at what they’re doing even when things are confusing. Taking the first step in choosing this lifestyle is huge, but it’s what comes after it that makes all the difference. This is something I’m learning every day!


Sara November 1, 2012 at 11:33 am

You can get rid of that smiley on point 8 by turning off that function in Settings -> Writing.
There’s a checkbox next to the following:
“Convert emoticons like 🙂 and 😛 to graphics on display”



Sean November 1, 2012 at 12:58 pm

I know I can, but I think it adds character 🙂


Kris de Leon November 4, 2012 at 6:37 pm

Thanks Sean! I really liked how you mentioned you’ll be focusing your posts on “what’s in it for us”. When I read that, I continued on and started reading further down. The “sense of urgency” really struck me. I sometimes feel too comfortable in my day job – I enjoy it, I’m building some solid skills and getting steady income. On the other hand, I haven’t challenged myself enough to build up my blog and community at the level I know I’m capable of, and achieve having a location independent lifestyle. Reading this post reminded me to create a sense of urgency for myself, even if there’s no immediate need for me to do it right now, and just push myself out of my comfort zone – before it’s too late and an external situation forces me to do so.

Thanks again, and really looking forward to participating in your community!


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