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Make Choices So You Have Choices

Updated: Sep 29, 2022

Statements I hear too often; “I hate my job.” “I hate my boss.” “When I retire I will be happy.” Statements I don’t hear enough; “I love my careers, all of them.” “I don’t like my boss, but it doesn’t really impact my life.” “I don’t want to retire, I love working.” Which statements do you make on a regular basis?

I’ve never understood why people consider having one job, working for one boss at one company to be the “safe” way to manage their career. We spend our entire life until our early 20s educating ourselves, determining what we want our future to look like, deciding where we want to live and who we want to marry and then we willingly turn the keys over to other people (sometimes one person) and let them drive us where they want us to go. That makes absolutely no sense. Imagine if the careers of musicians were determined by one person liking or disliking their music. Or if your favorite BBQ restaurant were closed because one vegetarian disapproved. Or the success or failure of a novel were determined by a single reader.

To put your livelihood and the financial security of your family in the hands of a single person, usually someone you barely know, is the very definition of risk. And while I’ve worked with some really great people, I don’t know anyone that would have put their job security before mine.

Jan Koum, co-founder of WhatsApp Inc., actually applied to work at Facebook and was not hired. As it turns out, he developed WhatsApp and Facebook bought his company for $19 billion! Not only is that a great lesson in perseverance, but it illustrates the risk/reward dynamics of working for someone else versus working for yourself. When he applied to be an employee of Facebook, they controlled his fate and they decided, for him, that he couldn’t work there. Later, that same company highly valued what he created and HE controlled whether or not he would agree to sell his creation for billions of dollars.

I’ve never been fired from a job, fortunately. I worked for other people, helping them with their problems and helping them achieve their goals until I was 33 years old. But, I worried every day that my efforts weren’t good enough and the reality that one person’s opinion of my work was the cornerstone of my fate was a persistent thought in the back of my mind. It wasn’t until I co-founded an IT consulting company that I started to realize how much control I could have over my own success or failure.

~ You Can Do Many Things ~

Depending upon the labor statistics you look at, people entering the workforce today can expect to have 15-20 jobs in their lifetime. I will end up at about half that number, but I’ve had a wide-variety of jobs in completely different fields. Since college I’ve worked as a stockbroker, a television writer & director, a webmaster/project manager and then a CEO, CIO and COO over the last 15 years. At first glance, those jobs don’t seem to be related in any way. But, every experience I had taught me something and every person I met opened a new door. I could not have done any of those jobs without having learned from the previous position.

The biggest lesson I’ve taken from all of those positions is that we can do anything for a living as long as we’re willing to learn how to do it. And that simple fact creates boundless choices in today’s marketplace.

We live in a world where teenagers are developing apps and NFTs and making more money than their parents. People that have left the workforce are developing products and selling them on Amazon so they can stay at home and raise their kids. Artists and entertainers and even scientists are earning money by creating Tik Tok and YouTube videos. Entrepreneurs are creating new products and services and raising money to start their companies through crowdsourcing web sites. Parents are driving for Uber and DoorDash on the weekend to help pay for their child’s education or save money for retirement.

You can search the phrase “millionaires have multiple streams of income” on the internet and you will see dozens of articles illustrating that a common theme among wealthy individuals is they have multiple streams of income. That makes sense. Real estate entrepreneurs branch out into rental property, house flipping, painting and construction projects. Business owners regularly have multiple small businesses. Entertainers want to sing, dance and act. And professional athletes are always trying to get the big three endorsement deals; shoes, soft drinks and cars.

I would argue that having multiple streams of income is important for everyone, not just millionaires. Whether it is simply relying on a dual-income household or generating income through a variety of channels outside of your day job, for every skill set you learn or product you create that you can sell to an audience, you lower your dependency on one job...and one boss.

~ Choose Personal & Financial Freedom ~

When I was working in corporate America, I never found the individual tasks I had to perform on a daily basis to be stressful in the truest sense of the word. Real stress for me started when I felt I had no choice but to continue doing what I was doing regardless of how little personal satisfaction it brought me. In other words, the more I felt I was tied to one option, the less freedom I felt. So, I made certain choices that allowed me to be available for future choices down the line.

I believe creating multiple revenue streams for yourself translates to personal freedom. You get to explore multiple interests, challenge yourself in different areas of business and culture and if you get tired of doing one of your “jobs” you can simply stop doing it, knowing that your entire livelihood is not tied to that single activity.

You can choose to start right now. You don’t have to quit your current job (yet). You can start down the path of personal and financial freedom by choosing just one activity that interests you and then scanning the marketplace to determine if anyone will pay you to perform that function. Good luck!!

~ Summary & Actions ~


  1. Don’t stake your entire life on the opinion of your boss.

  2. Find ways to diversify your income streams.

  3. If you’re just entering the workforce, you’ll have 15-20 jobs in your career.

  4. Choose your passion, define a marketplace, package a product or service and create multiple revenue streams!

Take Action Today:

  1. Define your skills.

  2. Define your passion.

  3. Marry the two to create a list of new career options.

  4. Define the marketplace.

  5. Package a product or service.

  6. Start selling.

  7. Repeat to generate multiple revenue streams.

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