Why Everyone is Holding You Back

By Sean Ogle •  Updated: 01/29/22 •  6 min read

This post was originally published on Location Rebel in October 2010, right after I returned from a year of living in Thailand after quitting my job. I’ve kept it published because I think it’s important to see the mindset of someone less than a year into quitting their job and starting their own business. You’ll have ups and downs. Learn what is holding you back, and focus on yourself.

For the longest time I had goals in the back of my mind that I’d been hoping to take action on, but wasn’t.  Things like traveling to Brazil to dance in the carnival parade, starting a business, and living abroad; these were all vague concepts that I’d wanted to explore, but my traditional American mindset kept me from actually doing anything about it.

Or did it?

It took me awhile to realize it, but it wasn’t just my mindset that was holding me back.

It was actually the people that surrounded me who were keeping me from pursuing the things that actually got me excited in life.  You see, (unhappy) people who follow a traditional way of thinking have made it their goal, consciously or not, to make sure you follow the same path they were on.

For many people, this could be in the form of a boss who’s been unhappy in their job for far too long – and they want to see others follow in their footsteps to validate the decisions they made.

It could be parents who are 22 years into their 30 year mortgage that worked for the same company for their entire career – and feel that you should do the same.

Or maybe it’s even your best friends that are pulling down 100k a year and cruising around in their new BMW’s – it can be pretty tough to tell them you’re quitting your job to head to the islands in SE Asia for an indefinite period of time.

(Don’t think I don’t see the irony that I’m now making six-figures and am onto my third BMW).

No, for most, their personal mindset is just a small portion of what keeps them from being unconventional – it’s the mindset of everyone around them that really hinders action.

What is Holding You Back?

I’ll provide an example from my past.

When I was at my previous job, there was a period of time where the stock market was crashing and revenues in our company (along with every other financial company in America) were taking a hit as well. My boss mentioned on a couple occasions that if I had any creative ideas for saving the company money, he’d be open to them.

This was right around the time I began Location Rebel. I wrote a post called “Sail the World – for Free”, which you may surprised to find, wasn’t actually totally theoretical.  I met a guy who needed an extra crew member to help him sail his 47 foot sailboat through the Caribbean.  All expenses paid, aside from the $250 plane ticket down to St. Maarten to meet him.

Dream come true right?  I was going to start my newly founded bucket list off with a bang and immediately cross off #13: Learn to Sail. I proposed a 2-month sabbatical that could have saved the company upwards of $10k, and I’d get to have a pretty life-changing experience.

Now I’d like to think the reason that he didn’t go for it really was that I was indispensable, but given the nature of the company, I don’t think that was the case.

Rather I think it came down to the fact that they weren’t afforded the ability to take such a trip themselves, and certainly didn’t feel as though I should have the ability to do so.  Hell, I was just a 24-year-old kid.

I shouldn’t be able to do stuff like that until I reached retirement.

I’ll make another much longer story shorter, but when I submitted my remote work agreement a few months later, I believe the reason it wasn’t accepted wasn’t due to anything business-related (after all they would have saved tons of money, and I would have been able to do nearly everything I did in the office remotely), but for the same reason that I didn’t get to sail.

I would have had a baller lifestyle, while they were unable to.

Side note: Yes, 25 year old me who originally wrote this really did say “baller.” It wouldn’t be the last time, either. Cringe…

I suppose that’s the price you pay for being young, ambitious, and full of creative ideas.

I’d like you to think about this for a moment as it pertains to your current lifestyle and your goals for the future.  What do you want to be doing that you aren’t currently making progress towards?  Is it because of financial reasons?  Fear? Other priorities?  Or have other people in your life determined your current path without you realizing it?

The vast majority of people around you will discourage you from living an incredible lifestyle, simply because they don’t have the courage to do it themselves.

Or in some cases, they didn’t have that courage when they were younger and now are stuck with an overwhelming amount of responsibility that stands in the way of that change.

I’d like to make it clear that I know there are a ton of people with careers they love and “conventional” lives that are perfect for them.  Don’t think I’m talking crap about you, if you truly are content with that, then that’s awesome and I’m stoked to hear you found that happiness.

No, I’m writing this for the people who aren’t being honest with themselves.  The ones that are living a mediocre life because it’s the easy thing to do.

I have a course inside Location Rebel Academy called Overcoming Uncertainty. In it, one of the things I ask people to do is write down everything that’s keeping them from taking action towards their goals.  For most, the honest answer is going to be related to someone else.

You’re working on your boss’s terms and can’t break out of that…

You think your parents would be disappointed…

Maybe your spouse or friends don’t get what you want to do…

I encourage you to take an honest assessment of your situation and think about the people who may be holding you back.

Then ask yourself if you’re happy with being held back.  If so, awesome, nothing left for you to do.

If not, it’s time to start doing some work and figuring out how to start kicking some ass.

So who is holding you back?  Is there anyone in particular that is dictating how you live and the decisions you make? Recognizing that is one of the best steps you can make to mentally prepare for any change you hope to make in the future.

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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