Is Everything Going to Be Ok? Well, it Depends

By Sean Ogle •  Updated: 07/11/17 •  7 min read

There’s a proliferation of bloggers in this world that love to scream the mantra “Just leap! It will all work out!”

Or any number of variations on that concept.You Know What- It Might Not Work Out…

But you know what?

The true reality is that, when you’re asking yourself “is everything going to be ok?”. 

The answer might not be the one you’re looking for.

In 2009 I left my job, moved to Thailand, and have built a lifestyle business that has grown far beyond anything I ever expected.

But the reality is, I’m the exception, not the rule.

Don’t get me wrong, there are thousands upon thousands of exceptions.

But there are also millions who will give varying levels of effort to start their own business in hopes of leaving their job and the majority of them will fail.

And I’m guilty too.

Over the course of the last 8 years, there have been plenty of times where I’ve encouraged people to take a chance and see where it gets them – after all, it worked out for me.

I think anyone can be successful on their own. This is assuming they’re willing to work hard and willing to try different avenues until they find the one that’s the best fit for them.

I also think that not everyone will be successful.

Let’s face it, it’s hard to start a business. The steps to get going aren’t difficult on their own, but staying focused and resilient long enough to see success? That’s a different story.

Most people read books like The Four Hour Workweek and have this image in their mind of throwing up a website, and boom! In two weeks they’re rich with a solid passive income business.


I’ll tell you right now, it takes months, if not years of hard work and hustle to truly create the assets to have a long term business.

For Location Rebel Academy, I market helping you make your first $1,000 in 3 months. That’s a completely reasonable and attainable goal. But it’s not like after 3 months your work just ends. You have to continue grinding, networking, pitching, and working to maintain and grow that.

Having been helping people create businesses like this for about a quarter of my lifetime now, I’ve definitely discovered a few truths and realities that are important to keep in mind as you’re getting started. These will help you keep your expectations in check, while also put you in the mindset to achieve success.

Everything is Going to Be Ok, If….

If you really want everything to work out for you, and you want to become the exception and be the one who succeeds in whatever it is you’re doing, there’s a few things you need to learn and do.

Some of it is a mindset shift. Others are routines and habits you build, and below I’m going to share some of the specific things I’ve done to make sure everything has worked out in my facvor.

#1: You learn create your own luck

It doesn’t matter how hard you work, how well you follow instructions, or how good your website looks – anyone who successfully creates a lifestyle business does so with a little bit of luck.

The good news is you can create your own luck.

My move to Thailand didn’t happen by accident. I spent 6 months blogging about my quarter-life crisis, and my desire to make a big change (check the archives and look at the Summer of 2009). I reached out to others, I made connections, and I proved that I was truly ready to make a change. Then Dan came along and gave me the opportunity.

You don’t always know when luck will hit, or how it will hit – but you have to be willing to put in the work and out yourself in the position to get lucky.

The best way to do that? Play offense.

Too many people have a “defense” mindset when it comes to making changes in their life. They play it safe, wait for things to come to them, and the reality is, they don’t get “lucky” because they’re not putting themselves out there enough and forcing luck to come their way.

#2: You learn to withstand criticism

These days, the concept of starting an online business or brand isn’t quite as taboo as it was a decade ago. We’ve all seen stories of regular people becoming YouTube or Instagram famous, or normal people making it online.

But when it comes down to support from those closest to you, there’s a good chance not everyone will be 100% on board – and that’s ok. You just need to be willing to persist. Often all it takes is one small win. All you need is one small win to build your own confidence and convert the naysayers around you.

But the work it takes to get to that one small win is the hurdle most people will never get past.

It’s also worth noting criticism doesn’t just come from the people you know. If you’re pursuing freelancing, blogging, or anything else that requires you to make a pitch, be prepared to hear the word “no”.

Like, be prepared for a lot of nos.

It’s easy to get beat down and feel dejected after even one person saying no. But when you sign up for this, you’re signing up for not just one, no, but dozens of them. Hundreds maybe.

Build a thick skin, have confidence in what you’re offering and don’t let that criticism get to you. Do that, and you’ll be way ahead of the game.

If this is a big problem for you, a little rejection therapy might help.

#3: You eventually, take a leap

In the beginning of this post, I decried the fact that so many people like to spread the “take a chance” mantra without thinking about the repercussions it might cause.

I’m more risk averse than most, so if I’m going to leap, it’s going to be calculated and well thought out.

When I moved to Thailand it was very much with a “what do I have to lose?” mindset.

Worst case? I run out of money, have an amazing adventure and get a job back in the States.

Best case? Well, 8 years down the line I’m doing exactly what I’m doing now.

I knew the risks, I knew there was a good chance I’d fail, and I was ok with that.

As you build your business and begin to see some success, you should prepare yourself that yes, you might, in fact, need to leap and take a chance if you truly want to make this lifestyle a reality.

But this isn’t something you should do hastily, blindly, or because some blogger with a questionable level of success of their own told you to.

It should be because it feels right, you have some confidence and momentum, and because you understand what the worst case scenario is, and you’re ok with that.

So, Everything Might Not Work Out. But…

Here’s the deal, it might not work out.

Actually, you know what, it probably won’t work out.

But that doesn’t mean you shouldn’t try. And if you stick to your plan, are resilient during early setbacks and can handle the teeter-totter of entrepreneurial emotions, then you know what? There’s a chance you might succeed.

You might build a business that will support you for years to come, give you the freedom and flexibility to spend as much time with your friends and family as you want, and most importantly give you incredible stories you’ll be able to share with future generations.

And to me? I think that’s something worth taking a chance on.

Note: See the #32 on the most important lessons I’ve learned.

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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10 comments on "Is Everything Going to Be Ok? Well, it Depends"

  1. Martin says:

    You really never know. You owe it to yourself to at least try to see what you’re made of.

  2. Gary says:

    Good article. Thank you. Been hemming and hawing over whether to join location rebel. I have been self employed before so I know the pitfalls and setbacks. I’m going to pull the trigger and join. I need to re invent myself. I’m working on a web site through Wealthy Affliates as well. Affiliate marketing training web site.

  3. Garin says:

    Great stuff Sean! I quit my job to start a business because I thought that was the entrepreneur’s right of passage. And subsequently I was dead broke for two years. It’s easy to blame lack of success on your day job and not having enough time, but in almost every case that’s not the #1 obstacle. It’s lack of focus, lack of skills, lack of a good idea, etc. And it’s WAY easier fixing those deficiencies on nights and weekends when you have a day job as opposed to having all the time in the world but freaking out thinking “I MUST make $X by this weekend to make rent!!!”

  4. Halona Black says:

    I absolutely love it! People use the probability of failure as an excuse not to try. When the truth is that there are so many things to be learned from failing. All failure means is that you need to find another way to get what you want. If you start an online business and it “fails,” what about it actually failed? Rather than throw in the towel, ask yourself some questions about what may have gone wrong. Then seek out answers from people who know more than you. Being an entrepreneur is all about building up your resistance to failure and being brave enough to move on.

  5. Marta says:

    Thanks for this post Sean, you put into words what I realized over the past weeks, when I took the decision to take a leap of faith and try with my writing business. I understood that there is a chance I fail, but I feel that I am ready to take even this. And without trying, I would never know what could be 🙂

  6. Eugene says:

    “You just need to be willing to persist. Often all it takes is one small win. All you need is one small win to build your own confidence and convert the naysayers around you.

    But the work it takes to get to that one small win is the hurdle most people will never get past.”

    Yes, very well said!

  7. Ana says:

    Excellent points, Sean. I haven’t joined LR yet only because my day job pays so low, I only have enough for food, rent, gas, etc., at this point. So I actually need to make a tad more on my own before joining.

    Something else hit me after reading this: Yes, we have to be ready to fail, in many cases more than once. But at 63, I have less room for failure than I did in the past, far less time. All I have to look forward to in the next 3 years is Social Security to replace this horrible job, and by then I’m truly hoping my business will have been up and running for a while. It’s all the hope I have. But it’s hope. And that’s better than nothing.

    1. Carlos says:

      Hi Ana,

      I am curious about your progress in that project. The fact that you’re making this bold leap into online self-employment rather late makes it very interesting. Do you have a blog where you chronicle that journey into becoming your own boss? I would like to follow.

      Wish you luck. I plan to do the same thing myself, at 58, starting next September.

  8. I am happy that you opened up the reality that I might fail, but at the same time you have inspired me saying that to keep trying. I wont give up I will try till I see success. Very good article I love it

  9. Will Robins says:

    Funny how many “overnight” successes took years building.

    It May Not Work Out… but… IF IT IS TO BE IT’S UP TO ME!

    Good Post!

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