The Risky Business of Not Taking Risks

By Sean Ogle •  Updated: 05/26/15 •  4 min read

It was my senior year of college, and my whole life I’d been playing it safe.

I chose where to go to school, not because it was necessarily the perfect fit for what I wanted to do – but because it was the safe play.

I lived with my best friend. I was an hour drive from my parents. It was in a small college down where everything was well, easy.

Just a few months from graduation, I was teetering on the edge.

No really, I was standing atop a 200 foot bridge attached to a giant rubberband seconds away from plummeting to my near-certain death.

Looking back this was kind of a pivotal moment for me.  In many ways, it would foreshadow the next 10 years of my life.

A series of swan dives into the unknown, but with every instance, just when I thought I’d hit bottom I’d be swooped back up into the sky in exhilarating form.

Leaving my job gave had it’s ups and downs. Getting engaged, buying a house, starting my golf business, working on the World Domination Summit – all of these things had inherent risks in them – yet where would I be had I not taken them?

I got an email last week from a reader that said this:

“Sean, I’m 31 years old, and unlike you I’m not a risk taker. I’ve been working as an accountant for the last 10 years, and am miserable.

Every year I say “this is going to be the year I do something about it” yet for some reason, every year it just gets harder and harder. I need help. What advice would you give to someone who desperately wants to make a change, but can’t seem to make the leap.” – Andrew

Personally, I think the biggest risk is not taking a risk.

Life isn’t easy, but it becomes a hell of a lot harder when you don’t give yourself permission to work towards the things that will make you happy.

What’s riskier, leaving a job to pursue a lifestyle that will let you do more of your favorite things, or staying in the same position for a decade or two, only to find out years later you haven’t really done anything with your life.

At risk of sounding cliche, one of the most valuable lessons I’ve learned in life is the worst case scenario almost never comes to pass. And when it does? It’s probably not as bad as you think.

The exception to this is jumping out of an airplane without a parachute. If the worst case scenario happens, you will probably die – but other than that, it’s not so bad 🙂

So what’s my advice to Andrew?

Ditch the all or nothing attitude. When you’re unhappy and you see the only way out as, in your case, leaving your job, it can seem like a monumental mountain to overcome.

But if you set milestones and plan to do it in say, a years time – all of a sudden it can seem more manageable.

As a bonus, because you’re working in a positive direction, you’ll probably find yourself being less unhappy at work.

So how do you start?

First, start a blog. Even this might seem like a risk, putting yourself out there can be tough, But start it, don’t tell anyone about it, and then as you get comfortable slowly start spreading the word.

This might not seem like a game-changer, but trust me, it is. Here are 56 reasons why.

From there you’ll have developed a new skill set, a platform with which to grow your name and reputation, and you’ll have started the foundation for making a positive change in your life.

Will you need to take a few risks to get where you want to go? Sure.

But if you plan for them, what used to feel like jumping out of a plane with out a parachute – simply becomes a tandem jump with an experienced instructor.

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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