After listening to Andrew Wilkinson, a tech company founder and billionaire, discussing his new memoir I was all jazzed up about starting a business. It reminded of the feeling I had during the tech boom in the late 90s, when I was certain I was going to become the next gazillionaire tech company CEO or at minimum, a multimillionaire COO within a few years. Those were exciting times. I miss that sense of ambition, hope, purpose and drive.
So not for the first time, I thought maybe now is the time for me to focus on making money – a lot of money. Not billions, but at least millions. Having that much money would afford me a life of leisure where I wouldn’t have to worry about food prices, healthcare costs, taxes, insurance and pool memberships. I could buy a second home for snow birding. I could donate large sums of money to my favorite charities. It would be cool.
So why not give it a shot?
After all, I have all the time in the world now. Nobody is depending on me for anything. I could work 24×7. I have conquered the fears and demons from my past that challenged me during my business life. I know more now.
Immediately, I began thinking about what kind of business I should start (or join).
Within 15 minutes I stopped.
My conundrum is that my career experience, expertise and success has been in tech sales and management. Anytime I consider rejoining that rat race, I think “been there…done that…I don’t want to do it again”.
I’ve been offered jobs by former colleagues since I retired a few years ago. These were people I liked, in solid businesses, who had positions I was well suited for. I imagine the pay would have been decent but none of these roles had a multimillion dollar exit that I could could see.
I had chased money (and the security I think it would bring) all of my life. The jobs I enjoyed the most were not the ones that paid the best.
On the other hand, I started 3 different one-man consulting businesses. Two of these were moderately successful as part-time side businesses. One was a total failure.
I enjoyed the consulting work. The money I made was good. The work was rewarding and my clients were satisfied. The problem was, I enjoyed doing the work but not prospecting for new work. I loved when I had inbound demand for my services but not chasing new clients.
One thing Andrew said was that people don’t know what will make them happy. His advice when choosing a career or a business was for people to instead list all of the things they don’t like and don’t want to do. For him, those included:
- Early meetings
- Managing large teams of employees
- Business travel
So, after making his billions, he started another company where he didn’t’t have to do any of those things.
That makes sense to me. As I progressed up the ladder in my sales management career, I did the same thing. I intentionally turned down several higher paying, prestigious opportunities because I didn’t want to deal with:
- Business travel
- Corporate Politics
- Needing to be a “front man”/visionary leader (I excel at being an operator/manager/behind the scenes guy.)
- Cold call prospecting
So after my initial burst of enthusiasm, I decided a few things.
- I’m not going to wrack my brain daydreaming about what my business I should start.
- I’m going to read Andrew’s memoir and a book from the 1970s that he recommend.
- I started list of all the things I don’t want to do in my next role/business.
After I finish these three items, we’ll see if my enthusiasm for making millions wanes. I would guess there’s a high likelihood it will.
I don’t have a lot of money, but I have enough. My frugal, minimalistic life is relatively comfortable and immensely satisfying.
More money would make some things easier and open up a few more options for me. I’d use the money to hire someone to take care of my lawn. I’d eat better food. I’d own two different homes so I could escape bad weather and experience living in widely disparate places (perhaps I’d have both a small town home and a walkable city condo). I’d have a workout room that is large and climate controlled.
I’m just not convinced it would be worth what I would have to give up. For the most part, I have come up with workarounds that get me almost anything money can buy.
