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Should Boomers Consider Encore Careers?


David Bowie dies of cancer aged 69

The Eagles’ Glenn Frey dead at 67

For anyone in the middle of the Baby Boom generation (like me) these headlines hit like a ton of bricks.

Not just because we grew up listening to their music and they were rock icons but more importantly because they were our age and they died of natural causes. 

It’s one thing to hear about a star dying of an overdose or plane crash which could happen at any age…

… but when they are our age and dying of natural causes that is when our own mortality finely becomes real.

Until then  we all think that we are still invincible…

… still have more time ahead of us…

….still think there’s plenty of time to change direction…

…and we can one day do what we were always meant to do, right?

Eventually, though, we’ll be faced with the reality of how few precious years we really do have left.

Rest in Peace Harry Brockwell:


Harry Brockwell, 77, passed away on Dec. 26th with family at his hospital bedside.

Who’s Harry Brockwell and what’s he have to do with the other two? 

Before you start to think that this article is a downer pointing out that we’re all headed to the final stop at the pearly gates let me assure you it’s just the opposite. 

Before I tell you about my friend Harry let’s agree that both Davie Bowie and Glen Frey had incredible lives and got to live their dream.

That’s exactly what they have in common with Harry.

Living Your Dreams Can Come Later in Life:


I met Harry over 30 years ago when I was a young salesman entering the “information systems industry.”

(That’s the fancy word we used to use for cash registers)…

Harry had been a veteran “C- level” manager in several companies during the cash register days. When the industry moved to new microprocessor technology and started changing at lightning speed many guys like him were pushed to the side. 

(Sound familiar?)

Harry was a great salesman but his heart was never in to what he was doing.

At about 50 years old he was out of a job and had no prospects for regaining a position in the same field. 

I asked what he planned to do and he said with a very confident smile,

“I’m going to do what I’ve always loved, I’m going to cook…”

Second Careers Usually Happen When You’re Out of Options:


Harry told me this he had taken some cooking classes but had no formal culinary education…

That meant he had no prospects of getting a job as a chef. 

He said that he was going to take over the fast food concession at one of the local state beaches (which only have business in the summer) and become a restaurateur. 

After all, he told me, what did he have to lose (other than money ) if it didn’t work? 

“When you think about it,” he continued, “I really have very few other choices… so I have no excuse to not do it.” 

I thought he had lost his mind…

Here’s What Happened to Harry


When life pulls you in different directions you sometimes lose touch with people you meant to remain in contact with. 

Such is the case with Harry and me when I moved from that area and seldom returned to visit.

I hadn’t seen or heard anything about him for 25 years until I received his obituary from a mutual friend. 

When I read it I was at once filled with a feeling of sadness at the fact that a friend had passed…

… but more importantly I was overcome with a sense of celebration for the way he lived.

Through those years I would sometimes think of Harry toiling away at the concession stand barely eking out a living and feeling sorry for him. 

Boy was I wrong!

And now – as the radio host Paul Harvey used to say – I’ll tell you the rest of the story


Here’s the rest of Harry’s obituary, he lived his dream and because of that had very successful and fulfilling life:

Here’s the rest of Harry’s obituary, he lived his dream and because of that had very successful and fulfilling life:

“Harry worked in a multitude of positions in sales and general management while employed with various companies throughout the U.S. and Canada. His love of cooking led him into the culinary arts and after many years of work and service was inducted into the American Academy of Chef’s Hall of Fame in 2014. Harry was president of the Ventura Chef’s Association twice, and twice chapter Chef of the Year. He was awarded his chapter’s Lifetime Achievement award for his unwavering commitment to the food service industry. In 1997, he was the ACF Western Regional Chef of the Year. He supported culinary-education related programs by performing site visits to ACF accredited postsecondary school programs, and evaluating certification applicants. He also served as an on-site visit inspector for various military food service competitions. He was ACF Western Region Vice President 2005-2009 and was recognized for his monthly newsletter. In 2012 he received The American Academy of Chef’s Larry Conti Chair achievement award; ACF Presidential Medallions in 1993, 1994 and 1998 and was a 2012 recipient of an Antonin Careme Medal from the Careme Society.”

Bravo Harry

You made your life worthwhile.

Thanks for showing its never too late.

Steve Jobs Leads by example:

Commencement speech that speaks to  doing what is important to you…

These are 2 quotes from Steve’s commencement speech that spoke to me:

  • For the past 33 years, I have looked in the mirror every morning and asked myself: ‘if today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something.


  • “I didn’t see it then but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure of everything.  It freed me to enter one of the most creative periods of my life.” 

Encore Career is not synonymous with “Mother Theresa Syndrome”


Don’t be fooled into thinking that finding a new purpose in life needs to include philanthropic activities.

Every book I’ve read on the subject talks only about the corporate suit who quit but then went into managing a non-profit…

…or the bookkeeper who quit to go into become a social worker in the underprivileged areas. 

While that might be a noble thing to do and fulfilling for them, could you imagine Steve Jobs donating his time at the local computer club rather than spending it creating products that changed the world? 

For that matter, I can’t imagine Harry Brockwell spending his time delivering meals on wheels to the elderly, (it just wasn’t his thing).

Finding what you really want to do and then doing it is what matters. 

When you do something well because you enjoy it, others usually benefit as byproduct.

Two more favorite quotes from another genius:



  • “Insanity: doing the same thing over and over again and expecting a different result.”
  • “We cannot solve our problems with the same thinking we used when we created them.”

The most important action to take is to take action. 

That might sound ridiculous ...but the number one reason for not living your dream is the paralysis caused by the thought of changing our routines, the thought of living outside of our comfort zones for a while and the lack of knowing where to begin. 

We’ve spent our lives doing what we done and so it doesn’t take much thought or effort to just keep doing it.

Change is so traumatic for us we usually only do it when we have no other choice such as being fired like Harry and Steve. 

Whether change is forced on you or you’ve found the courage to jump off the cliff before being pushed taking that first step in the most important. 

Things usually start to fall in to place after that.

Planning can eliminate the fear: 

business failed

In my case I had both the scenarios.

For ten years I had a very successful business that kicked out a lot of cash flow and I could imagine a day when that cash flow was so automatic that I could retire and just collect checks and take them to the bank. 

In the mean time I was so bored out of my mind that I remember thinking, “the best thing that could happen to me is to lose this automatic base because it would force me to take action, and that action would be in a different direction.” 

Well the phrase – be careful what you wish for because it just might come true – is exactly what happened. 

Within a very short time the business crashed and my thoughts of simply driving to the bank every day to deposit checks was replaced with, “oh shit, what do I do now?”

crash and burn

 Like a pilot experiencing engine trouble I went into automatic mode.

  1. Trim the plane to maximize the glide. Translation – cut all unnecessary expense and limit the outgoing cash burn to as little as possible.
  2. Look for the closest safe landing spot. Translation – look for the next thing you’d like to do and point yourself in that direction.
  3. Breakout the emergency equipment and rations to survive on. Translation – liquefy equities and turn them into cash with a plan of how long that cash will last.
  4. Once down on the ground immediately get busy working the survival plan. Translation – Don’t hesitate, move forward with the plan immediately and stay on budget.

My planning made it clear that I would need about two years without an income before the new direction that I had in mind would start turning a profit that I could count on. 

Additionally the project would require an investment so I would need even more capital. 

Fortunately I had plenty of equity in real estate (including my California home) that I could liberate which would provide the means to achieve my goals. 



That’s exactly what I did…

Selling my home in California, moving to Florida, reducing my California living expenses to Florida living expenses and re-deploying my equity into re-directing my life has been the best thing that could have happened to me. 

For me, the answer was selling my house.

If I had been over 62 the answer might have been a reverse mortgage.

Either way the key to unlocking the door to opportunity was the liberation of my equity. 

What’s your plan?

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