Life Lessons From a Decade of Wantrepreneurship

Don’t Do What I Did

In the book, Stumbling on Happiness Daniel Gilbert says that if you really want to know how you will feel in a particular situation just ask someone who is already there. Daniel explains that we are fantastically bad at projecting into the future and making accurate judgements about the things that will make us happy.

Applied this means if you want to be a doctor ask a doctor how they like their job. If you are considering getting married ask someone who is married about their life.

The most common initial reaction to this line of thinking goes something like this. . . “My situation is different, there are too many variables, how can I possibly make a decision based on what someone else thinks?”

The answer is simple. People are a whole lot more alike than we care to admit. There is a reason why Game of Thrones is a blockbuster TV show, it appeals to many because deep down we all have very similar wiring.

I digress, I am getting a little carried away. This is supposed to be about learning from my mistakes, so here goes.

Life Lessons of a wantrepreneur

I took a job for the money.

This is not uncommon at all and I did it for necessity but when I reached a certain level of income I got scared to look for anything different. I convinced myself that I was living my best possible scenario and looking for something better was a waste of time. Furthermore, I also started to believe that what I had achieved was good enough.
I started to compare myself to people around me and noticed that by and large I was better off than most of them. When I would cross paths with someone of a much higher status I would reassure myself with the idea that they were somehow unhappy.

I accepted a promotion for the ego boost.

I knew at the time of taking this position that I didn’t want it but it would also put me into a position of power and responsibility. We secretly all crave this. . . Deep down I know this but this promotion was the wrong way to go about achieving this desire.
At the time I was intensely focused on working on entrepreneurial projects that just didn’t seem to be working. The new job entirely shifted my focus from my businesses to other pressing matters that needed immediate attention.
In the end, this promotion set my entrepreneurial pursuits back by several years. It also caused me an immense amount of stress because I didn’t enjoy the job, the industry, the people I was dealing with, and I didn’t care about the product we were selling.

I purposefully did little to get ahead in my job because it didn’t pass the corner office test.

In my job and industry there people follow a progression of gaining more certifications over time and moving to higher earning levels. I was in a fairly good position but I could have gained many more certifications than I did and ended up earning more money. I purposely did not pursue career advancement because I knew I hated the industry I was working in.
Lesson – If your job doesn’t pass the corner office test and you are not even mildly interested, get out. I have wasted almost a decade in a job that I initially started in order to give me the opportunity to start a real estate inspection company.

I got comfortable and stopped being hungry.

Shortly after getting a job in the oil industry I found myself making well over six figures per year and having six months per year off. I had what appeared from the casual observer to be a very good standard of living. When I was at work I would suffer through 28 days of 12 hour days all the while biding my time until I was off again. When I finally got off I spent 28 days doing all of the things I wasn’t able to do while at work.
Money came easily and was also spent freely. My family travelled extensively and bought a beautiful house. We burned through pretty much everything I earned. Life was really pretty cushy and I forgot what it was like to be hungry for something better until I had to go back to work. Then the cycle would continue.

I settled

When I was younger and first trying to make a living I felt marginalized. I felt like I was being looked over by gate keepers. Fancy corporate jobs were not easily handed out and businesses were actually pretty challenging to start. I was quickly learning from the school of hard knocks.
When I finally did get a job that allowed for a good lifestyle I convinced myself that it was enough. I believed that the job was too good to quit when so many other people were struggling to make a living. In reality, I was scared to lose everything. This fear is paralyzing and dangerous and can keep you in barely tolerable situations for decades.

I got scared of losing and taking risks.

Gary Vaynerchuck recently said in a talk, that he isn’t scared to lose everything. He actually welcomes the opportunity to lose it all because that will just make his long-term success a better story. This type of fearlessness makes him a ruthless competitor. It may also make him a little reckless, but he’s right, in the end, it will be a helluva story either way.
Embrace fear and uncertainty they are the stepping stones to a better life. We are unfortunately wired to shy away from fear and be loss averse, this keeps us alive but often prevents us from becoming our best self.

I didn’t finish what I started because I got sidetracked, not because I decided not to do it.

As I already mentioned I started my job with the plan of starting a real estate inspection company. I spent $1800 on training material and had it all planned out. I knew what I needed to do, I even had it on the calendar. I just didn’t do it. Once enough time had elapsed I didn’t even really think about it anymore. After several years the idea and the plan had died on the vine.
Still, to this day I think real estate inspection is a great business and I wouldn’t mind being involved. I wish I had pushed forward and taken the test and gotten the certification instead of doing what I did instead.
During the same 10 years I have also started and stopped things because they weren’t working or I lost interest. The difference is that I decided to stop doing them.

I isolated myself

My job has been such that I am always leaving. Working a rotational schedule away from home makes it hard to maintain long term friendships. It makes it hard to keep a regular schedule and participate in ongoing events. Things like coaching kids teams or regular meetups fell out of my vocabulary.
The truth is that I also stopped trying very hard. Once you are isolated and not involved with many things it is easy to continue down that road.
The other truth is that relationships and people can have a tremendous influence over your life. If you cut yourself off from people that could have a positive influence on your life you will stagnate.

I stopped sharing my art

Because I was trying to live the life of an employee with responsibilities, co-workers and expectations, while also living the life of an entrepreneur I shared very little about what I was doing with people in my life that could have been more helpful or influential.
If you are creating a business in a vacuum your business will fail. If you are trying to hide who you are and what you are working on you will fail.
This also meant that I felt I was not being true and authentic. Whenever I would have interactions with people I would have to decide who to be instead of just being me.

There is of course more but I will leave it with those lessons for now. To sum up I want to create an actionable list that I can follow and possibly you too.

Don’t take a job for the money. But, if you do, either make sure you love it or pivot into something else as quickly as possible.
Never do anything for the ego boost. Do things because you know they will move you in the right direction.
If your job doesn’t pass the corner office test or you find yourself not wanting to advance, GET OUT.
There is always more, don’t forget this. Never stop being hungry for a better life. Kaizen!
Don’t ever settle. If you find yourself justifying why you are doing something to yourself it is time to go.
Risk is a part of life. Embrace it. Ask yourself, what is the worst that could happen? It probably isn’t that bad.
Finish what you start if you still believe in the goal but don’t quit because you are just too lazy.
Push yourself into social situations. Live out loud and share your work. Connect with people and do what you need to do to maintain relationships and seek out new ones.
Share your art, whatever it may be, and get feedback from people.

That’s all folks