
Happy Couple in Grand Cayman – we just kissed a sting ray!
This week I made more money in 3 days than I made in the previous two months.
In terms of “speaker money” that means I made as much money as some people with traditional, 9-5 jobs, working honestly and hard, make in a year.
As wonderful as that all sounds, and it truly is a huge blessing, that also creates a few problems:
The more you make, the more you spend, the more you need.
When the money is flowing in you can’t save it fast enough. You start to see the cracks in the house you never noticed before and begin doing all the improvements; you notice the clothes in the closet are going a little out of season and go on a shopping spree; you plan on putting money into retirement and are advised by investment strategists to buy more real estate.
It’s a wonderful problem to have, don’t get me wrong, but it’s also vicious, because during the lean months or dry years you are wondering what the heck you did with the money you made during the best of times.
I talk a lot about money in this blog for speakers and entertainers because this is the single greatest issue in the history of this industry.
I know more formerly famous successful acts, authors, speakers, business owners, artists, who now, in the prime of life between the ages of 55-75, when they should be enjoying the golden years, are reaching for stars while scraping the bottom of the barrel in search of gaining former glory.
Last week I had a fascinating conversation with a man in his mid-60’s. A lifetime of hustling to provide, he was a multi-millionaire from the ages of 45-52, then suddenly he lost it all in an investment gone wrong, eventually losing his home, divorcing his wife, hurting his family, and then nearly dying in the hospital.
He’s been through it all.
Now, over a decade after it all went to pot, he finally has hustled by pulling 18-20 hour work days in his 60’s to make his way back and created success in a new field as a salesman, re-established his life, a new wife, family, and is leasing a home. His new business has just reached million dollar levels. He is already spending what hasn’t yet come in, and now talking about gaining his former glory, buying a multi-million dollar home and big yard, continuing to prove that he’s worth so much.
As I listened to his plans I offered, “I know I’ve not achieved all you have, but I’ve seen what you’ve gone through, the ups and downs. Could I make a suggestion? What if you just save the money that you have made, and not yet spend the money you haven’t made yet, and instead just travel, don’t buy a home and put roots down that you’ll barely use with a huge yard to maintain, and instead go places you and your wife have only talked about. You could live happily in any place in the world, set yourself up to spend less traveling than you would on a new estate in a mansion, and could live on less while saving it for some rainy days as you grow older.”
This may sound like odd advice coming from someone 25 years younger, but this man said he would like to do this type of life plan, but he’s just constantly trying to gain back what was lost. I hope he does what he wants with his last quarter of life, but I know for one thing – I personally don’t want to be hustling at that age.
As I approach 40 this summer, I am well aware of the trend of both the groups that have done it wrong and the few who have done things right.
What is the answer?
From what I’ve found, it’s to live as close to normal every month, regardless of what the month’s windfall of money might be, next month might be as dead as your lawn in the winter.
The question is: What is your annual income? If you can determine the minimal amount you need to live on monthly and feel comfortable, then that is the amount you live on.
Setting up automatic payments for you and family to live on, dedicated checkbooks and debit cards to the practice, and doing the same with the business. This one discipline, if you even attempt to be faithful with it, will save you much heartache in the future.
When big money comes your way as you find success in your career from the stage, congratulate yourself more by what you’re able to save than what you can now spend.
Investments are powerful things as well – real estate, stock market, bitcoin, retirement, gold & silver, use items – whatever you want it to be, just be careful, and diversify, and mostly set up automatic payments that force you to put the extra money coming in into something that is a little tough to get your paws on.
Cashflow is king in hard times. Keep plenty liquid, or at least able to be converted over quickly in an emergency. Perhaps hire someone you trust in the financial field to be your accountability accountant actuator. These crazy helpful people will question everything you want to buy, and they mostly won’t let you spend too much, and you’ll be forever grateful.
In 3 days this week I made so much money, it was incredible, my wife and I spoke as we sat on the beach overlooking white sand and turquoise water of all the things we could do with it that would be awesome for our life. But what are we going to do? We discussed the importance of continuing to let our clients pay our way to travel, have a great life, while I still work, and equally will be saving nearly all we just made so quickly for the possibly unstable months ahead.
That’s the best kind of gift we can give ourselves.

Photo at the Ritz Carlton in Grand Cayman, where 2 bananas cost $6

Jason Hewlett, CSP (Certified Speaking Professional), CPAE Speaker Hall of Fame, is a Keynote Speaker for the largest corporate events in the world. His primary message, The Promise, is essential for Leadership, Management, Sales, Marketing, Direct-Sales Companies, and is a combination of engagement and entertainment meets inspiration. Jason has even received standing ovations from IT guys. He has been acknowledged as life-changing by Conference Attendees, C-Level Executives and Hollywood Elite. jasonhewlett.com

Please click here to learn about how Jason Hewlett, Speaker Hall of Fame, introduces the opportunity for you, or someone you love, to have the gift of learning how to create a Career From the Stage and begin moving toward fulfilling a lifelong dream as a full-time speaker, performer, or entertainer.
I LOVE this post, Jason. Thanks for your honesty and transparency. Hard to find sometimes in this business.
The tough part about this business is that many will not reach your level or your salary – making it even more important to manage money, manage risk, and prepare for the future and lean times. The GOOD NEWS is that there are speakers out there making over a million with modest fees. But at the end of the day, it’s not about how much somebody makes, but how much they keep.
Thanks to my husband, not me, we have adopted some healthy habits that we believe will help sustain us for a life of longevity, especially being that speaking is our family’s sole livelihood:
– I am working to create 7 streams of revenue (best advice I got in this business – not to put all your eggs in one money-making basket). I am building 7 streams with the goal of each being enough to sustain us on a yearly basis – so that if/when one dries up – it’s okay. While my love is really for only one stream, I still work hard on the others because that one stream I love may not always be there for me.
– Even though my salary increases every year, we still maintain the same standard of living we always have. Translated: We still have the same “overhead” as a business and a family that we did in year one. With the exception of health insurance (don’t get me started) and a nicer computer.
– While we don’t always follow it, we believe in the mantra that it’s not about what you make, it’s what you keep. I already said this, but it is worth repeating.
– I’m always making space for the “low hanging fruit” jobs in this business, because they keep a consistent salary coming in – even in the lean times. Translated: I’m okay with taking jobs less than my fee to pad my calendar and keep the seeds planting and sprouting in a word-of-mouth business. There are many of these jobs, they are easy for me to get, they allow me to sell other streams, and they keep people talking about me.
– I’m always two or three steps ahead of myself – hustle is my mantra, never coast. It’s very hard to come back from being flat-footed. Consistent energy is better than nothing. A body in motion stays in motion. Waiting for the fee you like can be dangerous.
– I operate my business on a shoestring with as few hands in my pocket as possible. This means I choose not to hire a management company, I don’t hire employees, and I contract any work I can not or don’t want to do myself. It may mean that I have to answer my own phone, but it turns out my clients LOVE that. Even as my salary has grown, I am very careful about where I spend my money. I guess I’m kind of greedy. I like as much money as I can go back into my pocket and my business.
– And the last biggest lesson and hurdle for me – we don’t charge anything we can’t pay for at month’s end – in our business and in our personal life. Our goal is to carry no debt except for house payment. Yes, it’s hard – especially for a household where one parent is bringing in the paycheck. It means we don’t have a car as nice as our neighbors. It means that our vacations are more homegrown. It means that we are still living in the same house that we bought when we were first married. But it also means I sleep a little easier at night.
These things aren’t easy to do. And I slip up all the time. But they are good habits to aspire to. No matter how much money you make. I think we would be surprised that some of the people out there we assume are wealthy, are actually living paycheck to paycheck, and the ones we assume aren’t wealthy, are the ones who are storing away their treasures for that rainy day.
Thanks for starting the conversation, Jason. It is an important one to have.
Such a wonderful and thoughtful comment my friend. Thank you. Totally agree with what you’re saying. In other posts I have written about the challenges associated with even having enough money to live, this post the converse of that and how to save, no question. I admire what you and your family have created, this list is perfect to live by. Love ya.
This post is needed so much! I’ve had 3 NSA national presidents tell me that this issue is one of their biggest concerns. .. speaker who make lots of money and spend even more.
I could write a book about this. In fact, I am! The challenge is how to get people to look at and manage their money differently? Some simple changes can lead to a much happier, more productive and less stressful life.
Awesome. Thank you Martin. You need to write this book!