Taking Risks, Feeling Stupid, and Leading a Life You Love

When I left my job at the end of 2016, I did so on faith. This is the story of my journey and with it, a formula for taking risks.

The year leading up to my decision to leave was an emotional one. I’d spent an entire career with one company. I loved the company’s mission, my job, my colleagues and our clients so it was unsettling for me – at the beginning of 2016 – to realize that I was really unhappy. I tried to see the light at the end of the tunnel; I talked to the right people about it and got positive feedback, but after many months of trying to see a future for myself there, I just couldn’t. The only thing to do was to leave.

I am not someone who leaves. I don’t quit. So this word, leave – while it brought with it a clarity that I had been seeking – was totally unexpected. It gave me clarity… but no relief. The thought of leaving opened a list of new questions:

Where do I go?  Don’t know.

What do I do? No clue.

How do I leave? No idea.

What’s next? Nada.

I have always been a faithful person. I believe that when we are purposefully lined up with God / the Universe / a Higher Power, life is good. Things seem to work out for the better. Not that we’re comfortable all the time, but things move in the right direction. And it’s not like we can sit around all day, praying and meditating, and life will magically become all that we want it to be. I believe in action and a lot of it. Discipline and dedication. Consistency.  A strong work ethic. All of that – on a foundation of being lined up with one’s purpose in life - is what makes life all that we want it to be. 

In 2016, I talked to God a lot – more than I had in many years. I prayed and begged for direction. I pleaded for a direction so clear that it would be undeniable. I wanted a job offer that everyone would agree was too good to turn down, and everyone would understand why I had to take it. I wanted the easy way out.  

I didn’t get the easy way out. After months of losing sleep, trying to figure out what was next and hiding in the bathroom to cry, the only thing that made sense was to leave.

To be clear, it made sense intuitively - on a gut level. It made absolutely zero sense practically and I’m a practical kind of gal. Practically speaking, my husband and I had always been about 50/50 with our household income so leaving my job with no job lined up behind it was very risky. I carried our health benefits and we have 3 children. We knew we could make it 3-6 months before I had to be back at work full-time with full benefits.

Who leaves a job without another one to go to, or without at least a few clear prospects? No one. Because that’s a stupid thing to do.

But this is how it feels when we take a risk. It feels stupid.

It feels stupid because you can’t see the other side of it. Sure, you can place bets. You can calibrate based on experience. The more experience you have with anything, the more you know it and the less risky it feels. Likewise, the less experience, the less we know and the more risky it feels. 

Big risks feel super stupid.

You know how people talk about skydiving as “Why would you jump out of a perfectly good airplane?” Leaving my job felt like that. It was terrifying. Immediately after I gave my resignation, it felt like I had walked off a cliff – like Wile E. Coyote in the old Road Runner cartoons – standing in mid-air and then falling, crashing at the bottom.

But by some miracle, I didn’t fall and crash. I did, however, hang out in mid air for a long time. 

Sometimes the result of a risk is immediate: we know right away if we’ve won or failed. Sometimes we don’t know for a long time and we have to keep working it until the path forward becomes clear. 

Risk - and the scary, stupid feeling that comes with it - is temporary. The benefits, however, can be life-making. It reminds me of the final lines of Robert Frost’s The Road Not Taken:

Two roads diverged in a yellow wood, and I –
I took the one less traveled by,
And that has made all the difference

It’s never easy to take a big risk, to go in a direction you wouldn’t normally go. But for when you’re thinking about it, here’s my formula: 

  1. Tap into your gut feeling and trust yourself; have faith
  2. Understand the practicalities & the big picture
  3. Make your move
  4. If you don’t know the result right away, give it time and keep working it

In my case, I never found that full-time job with full benefits because what I wanted didn’t exist in a job description posted somewhere. I hung out in mid-air long enough to realize that the best thing for me right now is to be an entrepreneur. It still feels risky and I feel stupid many days, but it also feels very right. I didn’t know this formula a few years ago – I had to discover it as I went through it, but I keep following and am finding life to be better than ever.

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