Maybe you find yourself, sitting where you are in this moment, at a crossroads. Wondering if you’re on the right path. Running the ‘what ifs’ through your mind. Putting yourself out there to test out how it might feel if you just up and quit your job.

• How did you leave your full-time corporate career?
• Did you have a plan B and C?
• How did you deal with the uncertainty of it all?

^ I get asked these questions a lot.

Sometimes it brings it all flooding back: the letter I wrote, asking Jeff to look it over, the out-of-body experience of watching my own hands tremble as I folded the paper and placed it inside the envelope. I remember pausing for a moment before sealing it knowing there was no turning back for me.

• Where would my next paycheque come from?
• When would it come?
• Would there ever be a time that I would look back at this specific moment with regret?
• Would I someday wish I could reverse my resignation?

^ the answer to those last two questions is a hearty NO by the way.

I remember walking into my office that day, the air stood still and the only thing I could hear was my own breath. I handed over the envelope. And then, the immediate sense of relief, <<there I did it, I finally did it>>, and the fear that simultaneously came over me, and then there was the excitement, the doubt, the optimism, the fear.

I felt everything you can possibly feel in a single moment, but one thing is for certain, I never felt regret. Still to this day, there was never, ever any of that. That is how certain I was that I was on the wrong path when I sealed the envelope that day.

So, I wanted to lay it all out for you here, in case you are nearing a breaking point with your career choice. Trust me, it is a place that so many of us find ourselves. They say that the average person will experience 7 career changes in a lifetime, and while I am not sure if this is true, I do know that I have encountered countless people that were once lawyers or nurses or accountants before finding their way to something completely different. And before I go any further, I want to help you frame this juncture in your life. The career choices that you have made that brought you to this point weren’t wrong or incorrect. You weren’t lead astray. You didn’t waste any of your time or money. It is the cumulation of your past: that education, those experiences, the chance meetings, and intentional encounters that lead you to where you are today and that has made you into the very person that you are, at this crossroads, making these big pivotal decisions. As soon as you begin to believe that you have made a wrong choice for yourself, that’s when you’ve opened the door to let regret in, and regret isn’t welcome into any of this self-exploration you’re doing. Okay?

And by the way, I just want to say that I think that is pretty darn cool of you. One of the most underrated senses of liberty and self-discovery is realizing that you are on the WRONG path. The experience is equally as elating as realizing you are on a very correct path. So let’s start by taking a sec for you to bask in the beauty of where you have found yourself: at this turning point.

Next, and in case I haven’t already mentioned it in pretty much every single piece of content that I’ve ever written, I think entrepreneurship is pretty darn cool. From the second I stepped into this lane, everything felt right. Everything from the struggles and the hardship and the late nights and early mornings felt so darn right. So I want to collapse all of the precursors I experienced into a simplified list of considerations for you to explore what it is that you need to do.

You probably won’t wake up one morning and decide to quit.

It had been weighing on my mind for most of a year, maybe even two. I had recently made some internal changes in my job to try and see if that would fix the problem. When I realized that it didn’t, I knew I was headed toward a bigger change. It became more a question of “when will I?” than a question of “will I?”

Does the thought of needing to fall back on a previous skill frighten you?

I mean, I didn’t exactly cast a huge safety net, but I knew that I was a generally employable person. If worse came to worst; I could do private Occupational Therapy consulting (and yes I did some of that) I had two science degrees, I’ve waited tables in the past, I could do that again, I can write and I have always had a passion for sales and marketing. I felt I was generally a pretty employable person and that I would fall on my feet somewhere if need be.

Is a regular income truly a measure of happiness for you?

A steady paycheque has never defined my happiness. Yes, there are bills to pay, and if necessary I was willing to cut out everything BUT the necessities of life as I set out to find my vocational happy place.

Are you hardwired to wonder ‘what if?’ for very long?

Chalk it up to a major case of FOMO, but I can not stand wondering “what if” for very long before I need to find the answer to that question. Case in point, I wondered ‘What if I lived in another country?” at the age of 17, and a few months later I left with a duffle bag to live in Europe before I even finished high school. At the age of 35 I wondered “What if I created a tech startup?” and after I traveled the globe and raised pretty significant equity financing, that tech business later became a fashion retail store (we call this a pivot in startup land).

Would you describe yourself as someone who chooses comfort over courage?

Ok, I won’t get on most fair rides, I think those things are crazy… but I did jump out of an airplane (ok that was crazy too). My risks are more about betting on myself. Sticking my neck out, being vulnerable, putting my money where my mouth is and taking chances with life choices rather than playing it safe.

If you answered NO to the four questions above, you my friend, are headed for some scary and exciting changes. I’ve totally been there, and I’ll be right over here pouring a mimosa, ready to cheers you! And don’t worry if it’s still a secret, it’s safe with me.