Why “Playing it Safe” Is The Biggest Risk You Can Take
Even If It Doesn’t Feel Like It At The Time
When you are working a steady job, it seems like any move that takes you out of the job, and away from the ‘safe’ recurring paycheck is a risk.
But in fact, for people in most professions, refusing to change, refusing to take calculated, meaningful, impactful risks leaves you exposed to a much bigger risk long-term.
The risk that not only will you lose your job, but you will not be able to make a living doing anything else in the short term.
I’m not the first person to claim this.
This is one of the key points in Tim Ferris’ “The Four Hour Work Week”, Seth Godin talks about this in his book “Lynchpin”.
Hundreds of other ‘experts’ and start up founders swear by this message, and their most devout followers parrot.
And yet it remains ignored by 99% of people.
Just fitting in.
Just loyally putting in their 8 hours a day.
Not willing to take a risk for the life & career they want, so they wait.
They wait for some future date where they will have slowly earned the life that they actually want to live.
Except.. waiting won’t change anything.
I have experienced this first hand.
5 years ago I graduated from University with my Bachelor’s Degree in Japanese (hey, at least I didn’t study poetry), with 0 job prospects, 0 contacts, few applicable job skills and an even more lacking ability to present those job skills in a good light.
I started searching for jobs in the way that was the most comfortable for me, that involved the least short term risks of face-to-face rejection, embarrassment, or pain, looking at and applying to online job ads.
I was naive and thought of course, someone would give me the time of day, while in reality, the job market in my hometown was horrible (200+ applications for bottom-of-the-barrel jobs) and I had never worked official jobs before, making me the least qualified applicant even for retail jobs.
3 weeks in I was starting to get discouraged.
But I waited. I persisted.
I kept doing what was “safe”.
3 months in and I had all but given up on ever finding a job, and ended up falling into deep depression.
For the next 6 months, I could barely muster up the energy browse job ads, with every time I pressed send feeling as draining as a full blown sprint.
Some days I would eat my favorite foods and the flavor wouldn’t register properly, as if depression was somehow jamming the “delicious” signals to preserve the outlook that “everything sucked”.
First, I took a risk and devoted a part of my time to try to get jobs as a freelance writer. “Not a real job.”
This ended up paying off, and I got my first real gig, that paid $100 in cold hard cash actually it was over Paypal, so with fees it was more like $93.71 or something like that.. but still. felt pretty good.
And then, something finally changed.
My friend got me a part-time job as a Japanese teacher, and the work inspired me with the confidence & energy to rewrite my resume & open myself up to new job ideas.
Instead of “playing it safe” and trying to appeal to all potential employers with my resume, I tailored it for some entry level sales positions, and actually landed two interviews and a full time job within a few weeks.
My very first real job, selling radon gas measurement kits over the phone.
The only problem was, I hated the job itself, but as persistance is a pretty valued trait in telemarketing, I would probably be able to hold it down… which was a big priority after having been unemployed and felt like a worthless piece of garbage for almost a year.
I also desperately felt a need to move out from my parent’s house and live by myself… so I needed the paycheck, at least if I wasn’t willing to take something that seemed like a risk.
As a freelance writer, naturally I followed a few people who called themselves “digital nomads” and spent their lives travelling the globe while working from their computer.
Daydreaming, I looked up flights to known ‘digital nomad’ locations (places with very low costs of living and good infrastructure) and found a one way flight to Chiang Mai for $200 and some change.
“Should I go?”
I was tempted, but it seemed like too big of a risk, too much of a leap of faith.
I had saved up about $3000 from the part time job and the few weeks at the new job, which would last me maybe a “whole” month in Norway if I moved into a place of my own, and didn’t quit my job, even with my unstable supplement freelance income of a $200–300 a month.
But if I bought the ticket, based on what I had read, I could easily last 4–6 months in Chiang Mai, even if I didn’t increase my freelance earnings at all.
So I weighed my options:
- Stay in Norway, move out, work a job I hate, stay in a place I am not that thrilled to be in and barely make ends meet. Possibly descend back into depression.
- Stay in Norway, quit my job, keep living at home and try to compete in the local job market that chewed me up and spit me out for the past year. Possibly descend back into depression.
- Quit my job, go to Thailand, try to make it as a freelancer for 4–6 months and enjoy my life doing so.
To me it was a simple choice.
Option 3. offered the biggest opportunity and the most enjoyment, even if on paper it seemed like a risk. After all, if I failed I could just move back home, and try to find another shitty job.
The math seemed right for me, even if it seemed completely wrong and like a huge risk to most of my friends… but I didn’t care.
I had made my decision.
I went for it, flew to Thailand with a one way ticket and never looked back.
As much of a risk as it seemed at the time, it sure never ended up playing out that way.
This “risk” took me from a job I hated, depression & living at home, to the 4 most interesting years of my life, growing as a person, experiencing life as a freelance writer, full time elementary school English Teacher, and now, digital marketing consultant at an agency in Tokyo.
Had I stayed in my job, I would have not only worked a job I hated, but worked long term for an employer that earned a reputation for “exploiting people’s fear of cancer to make money”.
I would have likely moved out of my parents’ house prematurely, and because I would barely be able to make ends meet, I would likely stay in the job much longer than originally planned. Then, after 1–2 years of doing telemarketing, I might feel locked into a career in phone sales or at least consumer sales(that I don’t enjoy at all).
If I had taken the safe choice, I would likely not have been able to spend weeks at a time traveling Vietnam, Thailand, The Philippines, Japan. I probably wouldn’t be as confident and comfortable around people, with people now mistaking me for a confident extrovert.
I probably would not have as many friends as I have now, and I definitely would not have met my current girlfriend.
And finally, I probably would not have evolved into a human being that feels grateful to be alive. That sees opportunity everywhere, and is excited about his own future.
Good things don’t come to those who wait.
Good things don’t come to those who play it safe.
Good things come to those who are willing to take risks, willing to live on their terms, now, rather than later.
*** Please don’t instantly quit your job upon reading this post if you have no alternate source of income, a lot of expenses & limited mobility.
I was already making some money from freelance writing and as a single 24-year-old I was able to move to somewhere much cheaper than I lived to bring my expenses down to the point where I could almost support myself through the freelance income, and would only need to increase it slightly to break even. I literally lived on $500 a month for the first few months, if your financial situation is different, you need to either save more up front or find other ways to off-set the risk. For example, lining up a new job before quitting, but leaving yourself a 2 month break to experiment before you start, or going the side-hustle route.
