The Money-Making Opportunity of a Lifetime Is the One You’re Afraid to Take

Tim Denning

It’s okay to let your curiosity get the better of you.

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Going to work in metaphorical handcuffs is exhausting. Especially when the culture you work in promotes *not* speaking up. That’s how I feel right now.

My fiancé said it best: “Why are you afraid to leave your job? You’re bold with every other decision except this one.”

She’s right. I’ve been a coward. It comes from a strange place.

When I was younger we lost the family home. This situation forced me to overcompensate financially later in life. There’s a safety blanket of savings, and then there is my pathetic overcompensation of more than a year of f-off money. Nobody needs years of f-off money to quit their job.

The other reason I have been afraid to burn my safety blanket of a 9-5 is because of early startup failures. These failures left me with a mental scar of what it’s like to lose everything. It’s part of the reason I think I’ve spent a lot of time with homeless people. Strangely, perhaps, in my head, I thought I might have become homeless at some point. This is the fantasy mental illness helped create in my mind.

At one point, I believed I would never be able to work again after the last startup failure. I started planning a life without an income. I wrote down which distant family members might feel sorry for me and let me move in with them. I planned how I would justify them putting food in my mouth in return for me helping out with chores around their home.

The financial doomsday prepping got me nowhere. In the end, I managed to heal from mental illness.

How you know you’ve found the opportunity of a lifetime

Right now I have zero debt, no family to take care of, and healthy savings. If there is ever a time for me to take a risk with my career then it’s now. Yet, I flounder and hesitate my way to nowhere.

I work a job and then spend an enormous amount of my free time working after hours on my various side hustles. It’s not sustainable. Side hustles can turn into overworking if you don’t convert them into a business — once you’ve reached an inflection point and have the data that prove you right.

I have the data after seven years. I have enough business knowledge at the age of 34, and after seven failed startups and one successful business.

The harsh reality I’m coming to terms with is that the opportunity of a lifetime may not always be there. The market changes. Opportunities become old and so do you. If you find yourself thinking about an opportunity every day then that’s how you know. If you think about an opportunity once and then never think about it again, it’s probably a fantasy rather than a genuine path you should pursue.

The opportunity in front of me is something I can’t stop thinking about. It’s been like that for all of this year. Not taking action feels like madness.

The power of curiosity

Blogger Benjamin Hardy wrote, “Einstein said that imagination is more important than knowledge. Arden said creativity is more important than experience.” I’d add curiosity to Ben’s list.

Curiosity is a sign of what you could be doing.

Following your curiosity is how you keep work interesting. I’ve used curiosity for seven years to chase topics to write about. From Chernobyl Horses, to weird companies, to life as a royal, to the nightmare of social media influencers — I’ve always let curiosity guide my writing. Yet when it comes to work, I haven’t. I’ve played it safe out of a deep fear of possible financial ruin. It’s silly when you think about.

Fear is a compass

Whenever I’ve been afraid of something, fear has told me what to pay attention to. Entrepreneur Michael Thompson sums it up perfectly when he describes his own battle with work.

Over time, by doing the work that hurt, I discovered a real passion for challenging myself to get just a little bit better and I found myself eager to get out of bed each day to dominate the very thing that once frustrated me.

Challenging yourself to beat your fear can be deeply motivating. It’s certainly better than showing up to a virtual office every day and feeling empty. I feel silly because I know this to be true.

When I conquered my fear of public speaking it changed how I communicated. When I beat mental illness it gave me unstoppable confidence. When I realized I was incredibly selfish and it was preventing me from falling in love, I made a change that led me to get engaged to a woman completely out of my league.

Fears tell you the next level of your life. If now is level one of your life, then what you’re afraid of is level two of your life. You can use fear to level up.

This is the stupidly simple solution

Sometimes wisdom punches you in the face. I spoke with a stranger the other day about the story running through my head. They said this brilliant sentence:

You can always go back to a 9–5 job.

If you take the opportunity of a lifetime and it blows up in your face, there will always be 9–5 jobs to come back to while you recover, and eventually, rebuild.

That’s the answer I’ve been looking for, for the last seven years. The way you do work you’re afraid to try is by having money saved up, and by remembering you can always go back to the 9–5 work you’ve left behind.

And if you do go back to work, your brush with entrepreneurship or life as a creator will be a badge of honor many employers will value.

I’m not there yet. I haven’t made any decisions. But I’m getting closer to realizing what I want to do next and that feels incredible.

How about you? Have you felt like this before?

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Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship www.timdenning.com

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