ILLUSTRATION: PAUL BLOW

“I want to be my own boss.” 

This seems to be the refrain of people everywhere I go, especially under 40. In our society, 75% of people think entrepreneurs have a high view in society, and 60% of millennials consider themselves entrepreneurs.

However, millennials are on track to be the least entrepreneurial generation in recent history, says The Atlantic. Mid-career entrepreneurs are also nearly five times more likely to have a running business five years later than those starting a business right out of college.

There is a trend among millennials to idolize entrepreneurship. We’ve grown up with shows like Shark Tank, Silicon Valley, and Billions, where the bold entrepreneur is the hero, or the Social Network where sticking a middle finger to the boss is admirable. 

While entrepreneurship can indeed be rewarding, (the richest people in the world are of course entrepreneurs), the goal shouldn’t be to be our own boss but to love our job by finding great work

The traits that make people love their work are:

  • Creativity
  • Impact
  • Control

These principles come from Cal Newport’s So Good They Can’t Ignore You. If we want to obtain a job that exhibits these traits, we need to possess rare and valuable skills. 

Image by Kurt Bostelaar at Leverlo.com

When I first came out of college, I had very little valuable skills, and I hated my first jobs. I couldn’t be creative in my work, I had little to no impact on my colleagues and customers, and I had almost no control, constantly being micromanaged. 

The benefit was that I could learn valuable skills on someone else’s bill. 

I chose the sales profession, so my first sales jobs was selling simple products that required little knowledge or expertise to sell. For me, this was print advertising. As I developed a sales process through experience, mentorship, books, and failure, I was given opportunities to sell more complicated, differentiated products. For me this was enterprise software. 

Financial gain is obviously an important piece of loving our work, but acquiring new skills is more valuable than financial gain. 

Early in my career, I was once asked to stay in a role I had rather than pursue a job in a different part of the organization where I would build a set of rare, valuable skills. The VP even offered a substantial raise for me to stay in my current role, but I knew taking the new job in the other department  would offer me valuable skills that would increase love for my work. 

If we have a unique set of skills, we are linchpins that cannot be replaced. We can vacation when we want and are needed by our peers and customers. Money will also follow. 

It may be a good idea to start a company, but we need to acknowledge that without a unique set of skills, starting a business will require an insane amount of sacrifice. The most common reasons people start businesses are: secure financial future, be my own boss, and set my own hours. Many of these can be learned at a 9-5 with far less risk.  

Some other things normal, 9-5 jobs can teach us include: 

  • Expertise and connections in a specific industry. 
  • Learning our unique personalities and skillset through employee and customer feedback. 
  • What we like and dislike in managers and bosses. (Here is the list I’ve compiled over my decade of sales experience.)
  • What we like and dislike from customers. 
  • What industry we prefer to work in. 
  • Where companies in our industry typically fail. 
  • Best practices and craftsmanship in our specific role whether that is sales, marketing, finance, management, human resources, etc. 
  • Lots of human contact and feedback that would be lessened if we worked by ourselves. 
  • Easier to ride out down markets when hard times come. 
  • Consistent income to provide us the ability to work on a side-hustle after hours. 
  • Make mistakes on someone else’s dime. 
  • Develop a repertoire of projects that can be referenced when moving to new jobs or starting our own business. 

Conclusion

While entrepreneurship is the best way to guarantee we are our own boss, and the most likely way to make us rich, most businesses do fail. The famous venture capitalist Paul Graham said that the total value of the companies he’s funded is around $10 billion, but just two companies, Dropbox and Airbnb account for about three quarters of it.

Corporate, normal, 9-5 careers develop unique skills that are transferable anywhere we go. They give us the ability to make an industry better and the joy of being able to solve complex problems. Rather than idolizing people that are their own bosses, we should idolize people that love their work. 

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