Live, Freelance Or Die: How Baby Boomers Can Make $50,000 A Year, Or More, Selling What You Know


If you’re a Baby Boomer and you believe retirement is either impossible or ridiculous, my goal is to help you learn how to freelance with great success. There are millions of us born between 1946 and 1964. We represent the most significant age wave in the history of the world! And millions of Boomers are kind of screwed right now because we either can’t or don’t want to retire. We want to live, work and retire, maybe semi-retire, completely on purpose. Maybe you can learn to freelance.

When I was nine I got to watch my father start the small business of his dreams. He wasn’t a freelancer until much later in life. I’ll tell you a bit more about my dad later because he’s one of my heroes. What happened set the stage for me to be the small business, sales, digital marketing and teacher, coaching guy I am today. I am a freelancing consultant, writer, coach and teacher. I’m going to tell you how I set myself up to NEVER WORRY about my retirement again.

Please consider this the first article in a series called, “Live, Freelance Or Die: How To Make $50,000 A Year, Or More, Selling What You Know.” This series is about seeing something you really want in life, like the freedom to own your own business, or to semi-retire or retire sooner than you think you can. This is about dreaming and going for what you want more than anything else. If you want to learn how to freelance I assure you there is money to be made.

My formula will teach you how to freelance and sell what you know; your skill, experience and knowledge. It’s about reinventing yourself and never giving up. As the infamous Nike ad read, “There is no finish line.” While death is a certainty, living, working and retiring on purpose is optional. Look around and tell me what you see – millions of people who seek more meaning, purpose, health, wealth, joy and freedom.

What Is Freedom?

Most people who have amassed a fortune will tell you time is worth more than money. I believe it, too. So, how much is your TIME FREEDOM worth to you? If time is more valuable than money, and you use your time wisely, how wealthy and healthy could you truly be if you committed to creating a plan for yourself? Learn to freelance.

This is for Baby Boomers because I am one. Freelancing is big business and it’s done by people of all ages around the world. The internet drove huge, new demand for training, coaching, programming, writing, designing and more. The beautiful thing about what we teach at is you can do what you want when you set the right intentions and follow through with your plan. Even if you don’t want to learn how to freelance, our community has tons of other resources to help you live, work and retire on purpose.

What Is Freelancing?

A freelancer is a person who is self-employed, typically with no employees, selling their time, labor and knowledge at varying rates part or full-time. Freelancing is one way to work for yourself without getting bogged down with traditional, larger capital investments and many risks associated with building bigger, “brick and mortar” businesses. Freelancing is a very real business if you treat it as such. What I love about freelancing is it’s a very simple business model compared to most businesses that require large investments to start. You can learn to freelance from home and use the tools you have now. But you will have to learn.

I’ve been freelancing for almost 15 years now. If I can do it you can do it. You just have to believe in yourself enough to face your fears, build a simple plan and take the necessary, next actions. Simple, but never easy.

If you want to learn how to freelance your way into semi or full retirement some day, or come out of retirement now and make a few bucks as a freelancer, keep coming back to If you want live with more purpose, joy and make a few bucks at the same time, freelancing may be the way to go.

My goal is to explain all of this freelancing and web stuff to you in a way you can understand. I’ll also give you suggestions and links to resources you can learn about on your own. This way you can apply what you learn as you go; as you DO. Nothing is more important than doing. See what you want, take the action to get there, learn as you go, never stop.

You will definitely need great access to the internet, a reliable computer and willingness to learn massive amounts of information you’ll filter and apply as needed. Don’t be intimidated. Just start learning and practicing. Breath deeply, a lot, because learning new technologies, languages and skills can be stressful. But it doesn’t have to be painful if you follow my formula and keep at it with tons of purpose powering you every day.

Freelancing does NOT require you buy a building, fancy office furniture or make big investments to start. Even though it’s a simple business to get started, you must start by finding ways to get customers to pay you.  The truth is I need very little to run my freelance consulting and coaching business, by design. Less overhead is more, trust me. I have a couple of computers, a sweet home office, a main office that’s virtual, several software systems we depend on, regular, digital advertising, constant social media, massive blogging and other basic business expenses I write off. I keep great books, tax records, customer files, back ups, and notes on everything because being a freelancer at the highest levels of the game requires you wear many hats and stay organized at all times. Treat your business right and chances are you will experience a way better business result over the long haul.

What Do You Want?

What do you want for yourself more than anything else? Freelancing is one way to help you generate an income and take control of your time.

Warning: Freelancing is not for everybody because the toughest challenge for most of us is finding and keeping enough willing, able, paying customers. If you can find your customers and keep them happy you will be happy when you learn to freelance your way to making $50,000 or more a year, if this is your goal and commitment. (No promises!)

Finding customers comes first. Yes, you want to pay yourself. This requires people paying you or your company first. If you want to work for yourself, do what you love, when you want, from the comfort of your home, van, RV or island, freelancing will require you to sell your thought leadership, experience, personality and more. And I will teach you the power of teaching more than selling. Nobody wants to be sold. You must learn to teach and sell which is nothing more than helping others get what they want. This is one reason I really love what I do every day; I get to help you maybe.

When you learn to freelance online, or offline, and your model  can  be virtual, like mine, meaning you can work from anywhere. You may not need to be in front of customers physically and this means your life can much simpler. You won’t have to commute or travel if you don’t want to. Because of this I’ve never found a more liberating way to work and live. No wonder I have so much fun teaching it.

I can’t promise you anything in terms of income, guarantees on what I did will work for you, or what is best or not for you or anyone else. I learned to freelance because I wanted control of my time more than anything else. Nothing is more valuable to me than my time, including money. In essence, I am a very wealthy man when it comes to my time. This has been true for me since 1991 when I quit my last “day job” which was an amazing career up to that point.

The Trudge Is Worth It

It wasn’t always easy. I trudged my way to where I am today because I want to work for myself and control my time and income as much as possible; freedom. The more business experience you have the better when you learn to freelance because you’re selling your knowledge, time and talent. I had a very successful business before I freelanced. It was a small business and I made a lot of mistakes after selling it. I also went broke after 9/11, but it wasn’t because of terrorists. It was because I imploded emotionally and spiritually, and that lead to losing my way for a while in my small business life. And that lead me to where I am today! It’s all good.

I had to have tons of help being a freelancer. My wife carried me more than once. My family stuck with me through it all and I am eternally grateful to all my friends and family because I wouldn’t be here were it not for all their help, love and patience. I am a blessed man to be a freelancing consultant and coach today. I also get paid to write, but not as much as I get paid to teach, coach, speak, etc. You will need help, too!

This is not about money although I do want to tell you that you can make a great living if you work hard at being a freelancer. I make no claim to being a millionaire, billionaire, or that this is about making money. It’s all about working part or full-time doing more purposeful and rewarding work. It doesn’t have to be glamorous nor will you likely become famous if that’s what’s driving you. Odds are against us all, but there is a way to do if you focus and follow the steps I’ll lay out. Believe me, there is plenty of room for more freelancers who know how to help others get what they want by selling what they know in coaching programs, workshops, books, membership sites, movies and more. The freelancer business is booming.

Luck will play a role in your success. Your success as a freelancer is most about managing your freedom in a responsible way. You will learn to freelance for freedom. You will live free, like me. I will die, happily. How about you?

Thanks Dad, Mom

Everything I stand for today as a husband, father, business man and entrepreneur I credit to my father and mother. They were the first people to show me how to live free or die. They did this by moving me, my younger sister and brother from just outside Boston, Massachusetts to Laconia, New Hampshire in the early summer of 1969. They bought into dad’s first business, a hotel in Laconia called, Shangri-La. It later became The Brickyard Mountain Inn. I watched dad, with mom at his side all the way, run that hotel, develop it, lose it and start over by the time they were 40. Magical, indeed.

Why the die part? The die part may seem harsh, but I grew up in New Hampshire where I enjoyed an amazingly-happy childhood. But death is part of living. More importantly, “Live free or die,” is the state motto of New Hampshire, a state I still call home even though I’ve been gone since I turned 18. Live free or die is plastered on every license plate to this day. The words were first written by General John Stark for a speech he could not attend on July 31, 1809. The ceremony and speech was for a ceremony celebrating the victory at the Battle of Bennington. Stark was too ill to travel to an anniversary reunion of the battle. His now-famous letter was first shared in a toast that read, “Live free or die: Death is not the worst of evils.” This affected me profoundly.

I got to watch my father and mother start and build more than one business before I left for college in 1979. My parents vision, courage and ability to do what they did in business, and raising our family, set the stage for my life as a small business owner and entrepreneur. Like my dad, I see myself as a creative, outlying misfit. And I get to live, freelance and die.

$39 A Minute?

In closing, here’s an example of how to freelance and get paid handsomely. I recently got paid $39 a minute to speak to a group of business owners attending a national conference. There were a couple hundred people in the room so it was nothing major beyond the honor to be paid to speak and teach at this level. (Talk about ROI.)

Here are some other examples more in the “sweet spot” of typical, freelancing gigs …

  • Writing, editing, publishing.
  • Teaching workshops, seminars, coaching programs.
  • Designing, programming, building and managing websites.
  • Coaching programs leveraging your unique skills, knowledge, experience.
  • Building and selling a membership site.
  • Working on ecommerce sites, including your own.
  • Project management.
  • Email marketing, blogging, social media management.
  • Public relations.

This is just the beginning if you want to learn how to freelance. If you have questions about freelancing, not dying, please ask me. Post them here on the blog in the comments section. Or send an email to me.

Get invited to our free, live classes, expert interviews, new articles and more when you sign up.

About the author


Founder and publisher of "Let us help you create the retirement plan, income and life of your dreams."