Are You Afraid to Bet On Yourself?
Betting on yourself is a lot easier said than done!
How many times have you really bet on yourself? Why did you make the decision to bet on yourself? Understanding why you’ve done it in the past might be the key to doing it again.
Back in 2008, I made one of the biggest bets I could on myself.
I worked in national account sales with an exciting client – Anheuser-Busch – and I was good at my job. However, I started to develop a feeling in my gut that wondered if I could be outstanding at something else. So, in the middle of 2008 just as the recession was underway, I bet my entire salary and 401k that my gut feeling was right. I placed a bet on myself that maybe I could be outstanding in another career.
This was a scary bet to even consider. It took me about 6 months of consideration and planning before I finally made the bet on myself.
One of the things that made it so tough was that I actually liked my day job. I didn’t love it, but I enjoyed it a lot. I got to travel a lot and go to Anheuser-Busch’s events and parties. For a 25 year old single guy, that was a fun job to have at the time.
To make a little extra money, I had a part time job teaching math at a local learning center. Those 6-10 hours a week started to become the best part of my week. That was the moment I started to question if I was in the right career.
When you know there is something out there you can be outstanding at, it’s hard not to pursue it.
Teaching math not only fulfilled me, but it also brought out my best in a way I had not experienced for several years.
After almost a year of scratching my itch for teaching math, I made the bold decision to bet my entire salary and 401k on reinventing myself into a math teacher.
Quitting my day job was one of the scariest decisions I’ve ever made in my life.
Not so much because of the money, because I had already bet over $100K on myself in student loans to go to university.
What made it scary was that in addition to the salary and 401k, I was going off the traditional path of success. Betting $100K on a university degree is what society tells us is ok to do because you get a degree, then a job, and eventually start moving up the corporate ladder and make more money. So that in line with what I was supposed to do.
Quitting my job, however, after I’ve taken those loans and must pay them back is NOT what we are supposed to do. What made it scary was the fact that I was getting off the path to success that was instilled in me.
I was supposed to…
Keep moving up the corporate ladder, not jump off it.
Make more money with each move I made, not give up my salary.
Pursue a more prestigious title with each move, not take a title that is often disrespected in some countries including my own.
Going off the traditional path is what made that bet so scary.
Add to that the fact that I did not yet have many of the skills I would need to be successful in teaching math. I didn’t have all of the experience I have today in speaking, coaching, teaching, and facilitating. Today I have these skills in abundance, but back then, they were skills I barely knew much about.
Yet somehow I found the courage to make that bet. After 6 months of consideration and planning, I devised a plan to mitigate as much of the risk as possible. In the end, my plan fell apart and I had to make it up as I went.
What made this possible was that deep down, I believed in myself, I believed that I would find a way, even if I didn’t know how when I started. I knew that I could figure it out even if I didn’t know how long it would take.
15 years later I find myself in a similar position.
I got laid off during the pandemic and since then I’ve been working to figure out how I could help others reinvent themselves and build lives aligned with their values, passions, and purpose.
Three years onto that journey, I finally have clarity about how I could do this and build a business around it. And just as I am getting that clarity, I’m running low on cash flow.
This time I don’t have a 401k to bet, but I do have my savings. I put money aside for ‘later’ and I never really defined what later meant. I’m not giving up a salary, instead I’m giving up on going back to a salary. Simply put, it’s time to bet on myself again.
This time, I am betting on myself to build a business that helps people around the world reinvent themselves in pursuit of their values, passion, and purpose. I’m betting on what I believe in my heart could be my life’s work.
For several months, I’ve been wrestling with this decision. I’ve considered looking for jobs or going back to doing things I don’t enjoy as much but pay the bills. With cash flow drying up and expenses at home getting higher with a new baby, I was worried that I needed to give up on this path and take a safer one.
And then I had a breakthrough on a call with my coach.
I realized I’ve never been more capable than I am right now. Today, I have more skills than I have ever had. I am the best version of myself I have ever been to-date. My supporting cast is the best I’ve ever had. I have massive experience in teaching, coaching, speaking, and facilitation. And while this new challenge will certainly require newer skills, I am certain that I can learn them too.
I know I can do this, I know I can reinvent myself again.
Why? Because I’ve already done it and with less skills, resources, and abilities.
This is my time!
If I invested in myself when I was 26 and didn’t have all of the skills I have today, how DARE I NOT INVEST IN MYSELF NOW?!
Are you hesitating to bet on yourself? When was the last time you bet on yourself? I am certain it was scary then and yet somehow you felt bold enough to do it. Now is no different. If you know this is what you are meant to do, if this is what you are called to do, then bet on yourself. Give it serious consideration and planning, but ultimately, know that you will find a way.
And if you need some help, I’m here to support you. DM me on Linkedin or Instagram. You have everything within you to make this happen, you just need to believe in yourself before you make that bet.