Fifteen years ago, this serial entrepreneur from New York opened a bar in Madrid. It was awesome; a glamorous money maker set up on foreign soil. You got to love it!

It ran smoothly for many years until the opportunity came along to sell.

I pulled the trigger. Now, what do I do?

My clients at the bar helped me decide. “Your English is so good; you should teach.” “Have you thought about teaching business?” I couldn’t tell if my clients, (often in an altered state), were kidding or sucking up to me for a free drink? No. I had never thought about it, although my degrees in Economics and English Literature ostensibly prepared me for a teaching career. However, opportunity and other circumstances led me to a life of a serial entrepreneur.

Reflecting on a career filled with hustling and running several successful businesses, working for someone else was not on the radar. With time and money on my hands, I traveled, pursued my interest in photography and started to write. During this period, I tried to dissect the how’s and whys of not just mine, but careers in general. The way I see it, there are three, and possibly a fourth phase of your work life. Moving from one phase to the next is a combination of experience, education, opportunity, and motivation.
For those of us not born with a silver spoon, the first phase of your career is working to consume. Typically, your first job in this “gig society” is part-time. The money earned is spent on frivolous things that your friends have, and you don’t. All of it to keep you socially flush. It could be clothing, music or other consumables you deem essential. You’re still living with your folks, so things are cool.

Then comes the move to college or university. Here the job you take becomes more serious. You now have real bills and the need to survive. Maybe you find a job in line with your desired career path, or if lucky, the work is related to your education. Perhaps the gig at McDonald’s or the Gap will teach you something about business, specifically retail or marketing. In the end, however, it’s a job to survive.

The third phase is where it gets interesting. You now have a degree in hand (those of you who didn’t slack off) and are now serious about starting your career in an area of interest or as previously stated, along the lines of your education or experience. Your job at the “Gap” may have given you a taste for retail or economics or a degree in English Literature may be pushing you into teaching. Whatever you choose, it is more critical. I don’t know about you, but the thought of marriage, kids, and the extras like a mortgage, cars, medical bills had me scared. But we take the plunge.

You now have an excellent cushy job with great benefits.

All of it deemed rational and the right thing to do. Most follow this pattern. Your career becomes enticing. It motors along with promotions, more money, more opportunity, but truthfully the extras leave you in a position of just surviving. To me, it was a trap.

This leads me to the possible fourth phase: getting beyond survival.

Start your own business! Rid yourself from the shackles of the ordinary! Teach English using the “autonomo” system in Spain. During the crisis years, the country modified the rules for working independently. Tax breaks and less paperwork made this option attractive. Once you have it set up, learn as much as you can about how to market, and manage your independence. You can take it further. Use your experience, knowledge, and motivation to develop a full-blown company. You will be free and live like a king!

For a complete analysis and a working model for doing this, find my new book on Amazon entitled “Hot Sticky Plastic Suits and 10 other material stories to help you retire early!”
Or to make your life easier, go here for my book on Teaching English to the Spanish.

Thanks for reading this. Saludos!