Thirty-Five: Choose Your Own Adventure

Reflecting on the choices that have led to where I am today.

My favorite movie in junior high.

The year is 1995. You are about to graduate from junior high school having served consecutive terms as school president, playing on the successful basketball team, and poised to be named class valedictorian. Do you:

  • go to the co-ed high school across the street, or
  • go to the all-boys private high school elsewhere?

You have chosen to go to the all-boys private high school.

Uh oh. The success you coasted to in junior high school is minimized as you shrink to a small fish in a big pond. Your social awkwardness with girls never recovers.

However, all is not lost. Personally, you make life-long friends. Some of them end up as groomsmen in your wedding. Academically, you’re still able to receive acceptance letters from solid — though not top-tier — universities. Do you:

  • go to college on the east coast, or
  • go to college locally?

You have chosen to stay local for college.

You start off strong after choosing a Computer Engineering major. After freshman year and part-time through sophomore year, you work a paid internship at Cisco Systems. After your junior year and part-time through your senior year you work a paid internship at Sun Microsystems.

At the time, these feel like great things to add to your resume. But after starting off strong, your academics suffer. You try to coast here like you did previously. You’re an even smaller fish in a bigger pond.

Following graduation, you apply to various jobs with no luck. Around this time, the girl you’ve liked since high school has moved back from New York and you start hanging out more. Do you:

  • continue applying for jobs and hanging out with that girl, or
  • go on a solo backpacking trip through Europe?

You have chosen to backpack through Europe by yourself.

You decide finding a job can wait. Although you try, you aren’t able to convince any friends to join you — including that girl you’ve been hanging out with. You write blog entries to keep friends and family at home up to date on your whereabouts. You explore, learn, and have a lot of fun.

But you can’t backpack forever. You return home two months later to live with your parents. Do you:

  • continue where you left off prior to your trip and apply to traditional jobs, or
  • take an offer from your cousin-in-law on the east coast to do technical IT consulting?

You have chosen technical consulting.

Things start off a bit sketchy. Your cousin-in-law embellishes your very limited/virtually non-existent consulting experience in order to sell you to clients. The exciting travel destinations you had in mind take you to client sites in exotic places like East Brunswick, New Jersey and Akron, Ohio.

Luckily, you’re a productive team member. Eventually your cousin-in-law refers you to another consulting firm and things change. You get a sweet deal. It’s your first real job out of college and you’re making six figures.

Even better, you continue to see that girl you’ve had a crush on and go steady. You realize you’re in love with her. Do you:

  • let her go to business school without you, or
  • propose to her?

Of course you propose.

She says yes. This ends up being the best decision you make. Ever.

However, other decisions still need to be made. You continue consulting but have shifted from the technical side to the business side. The money continues to be great — even during an economic downturn — but something is amiss. You feel like you’re leaving too much money on the table working for someone else’s consulting firm. Do you:

  • stick with the company and your plush job, or
  • start your own consulting company?

You have chosen to do independent consulting.

You are offered a role on a mercenary team of other independent contractors in Vancouver, Canada. It sounds interesting and pays more. Your greedy ass follows the dollar signs.

And then you go and ask for more money. And you get it. You continue to travel Monday through Thursday. The work turns out to be less interesting than you anticipated. In fact, you can’t stand what you’re doing. You start exploring jobs that wouldn’t require so much travel but can’t find anything worthwhile. Do you:

  • continue independent consulting, or
  • quit?

You quit.

It’s 2012. You’ve earmarked enough money to be jobless for anywhere from six to 12 months depending on your frugality. You decide you want to go back to your early career and start coding again. You buy some coding books but you’ve been out of the game for awhile. Do you:

  • continue to try to teach yourself web development, or
  • apply to this costly new coding bootcamp thing that has only had one previous cohort?

You enroll in the second Dev Bootcamp cohort.

You start learning to code again with the intention of building your own product after the cohort finishes. You think that, finally, you can build one of the many business ideas you’ve been writing down over the last several years.

But Dev Bootcamp also offers a day to meet with a number of companies and startups. You like to keep your options open so you go through some meetings and are eventually offered a job. Do you:

  • start your own company, or
  • join the startup?

You join the startup.

For the first time since graduating college, you are not making six figures. You learn a lot but it doesn’t work out.

You also have your first child and get to spend precious time with him. He’s amazing. But the time comes to decide what to do next. Do you:

  • go back to consulting but this time as a web developer, or
  • join another startup as a co-founder?

You join another startup as a co-founder.

Two classmates from your cohort at Dev Bootcamp begin to build a new startup and ask you to join. You take them up on the offer and spend the next three years learning and building. You are not close to making what you made before.

But you enjoy the work, the team is awesome and you really believe in the mission of the company.

You have a second child, a daughter this time, and she’s beautiful. You don’t get to spend as much time with her as you did with the first one, but you try to do what you think is best. Luckily, your amazing wife is still on maternity leave.

Today you turn thirty-five years old. The choices you make shape you. What do you do next?

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