I have made several large transitions in my working life. I started out working for companies and worked for some really great ones. But after many years, I began to tire of having the fruits of my efforts go to others and having others tell me what to do and what was important. I chafed at authority and the claustrophobic atmosphere. I just lost interest, patience and enthusiasm.

I felt like this was my one life and that I might be squandering it for paychecks and promotions. I looked around at the people I worked with and for and saw a lot of chronic situations born of poor behavior: divorce, alcoholism, gambling, poor health from lack of exercise and over eating. They traveled a lot for business and got paid amply and had expense accounts. These were all the trappings of success. They also had families and ex-wives and big houses to underwrite. Their poor behavior seemed like excessive behavior in response to deep seated dissatisfactions with their situation. They felt trapped and rebelled by abusing themselves with the tools of excess at their disposal. I wanted out.

Entrepreneurship

So I tried entrepreneurship and startups. I found it lacking as well. Its attractive because you are the boss and you can call the shots and you have the possibility of scaling an enterprise and cashing out. The cashing out, if it is successful, can leave you with enough money to not have to ever work again. This is what they call escape velocity money: where you have enough to escape the treadmill of having to make more to live on.

These reasons make a compelling rationale for bailing from the corporate world. And I relished in it for a long time. Until I didn’t anymore.

I grew restless and chaffed at another set of obligations born of another set of constituencies. When you are an entrepreneur growing a company you end up having a lot of mouths to feed and lots of folks to placate. There are lots of satisfying relationships that can be forged but I am now going to just list some downsides.

Investors

At first, getting funded seems like an unmitigated success. But investors can be royal pains in the ass. They are ultimately interested in the enterprise, and you as its avatar, making money for them. And they may have clauses in the funded documents that give them more power over you than you originally thought; maybe enough to boot you out even if you are successful in creating value.

Partners

Partners can be another source of problems. Someone in the know said its like a marriage but without the fucking. Greed and fear can make people act weird in the face of the prospect of money. Betrayal and palace intrigue can ensue and make your life pretty lousy.

Employees

Employees are another source of constant drain. You have to babysit them mitigate disputes. They can act like bad children and create toxic situations. Human Resource Management would be great if it weren’t for the people.

Customers

Big customers or client with buying power can also be a source of buzz kill. Bending over backwards to please an important client can really take the fun out of a situation. Its nice to be in a position where you can fire customers that are jerks.

All these reasons can cause fatigue and be really counter productive. They can make you question why you are doing what you are doing.

Solopreneur

A third option is solopreneur. And now with online business with a digital first strategy it is a serious option.

One can set up a completely automated sales funnel that delivers digital downloads or SaaS or other products and services worldwide. You have access to big markets with lots of customers and can deliver products that require no working capital or inventory.

This model allows one to have complete control and exercise autonomy and agency.

You have to enjoy doing it all and find every task interesting and worth executing well. This can have real advantages. I have found that the downside of delegating tasks is that I then lose interest in that task set and my skills either atrophy or don’t develop in that realm. If I have to do everything, then I am focused on everything and engaged in the whole process.

We now live in a time where robotics, automation, AI, chatbots, the internet and web create an ecosystem of support that can be leveraged toward enacting your dreams and ambitions. A group of dedicated worker bees performing the tasks you set for them 24/7.

And you can focus on building relationships and customers and providing real value.

I like it just being me and the robots.

It also helps to get off the hedonic treadmill and live frugally and with intention. Reduce your expenses and you may find it is not such a great leap to independence.

Then you can go back and pick and choose those relationships that add value to your life and you to theirs and not have to worry about having to please those who don’t deserve it.