The Baby-Boomer Dilemma

Best Business Ideas - The Baby Boomers Dilemma

The Boomers

Born between 1946 and 1964, the generation of roughly 72 million people known as ‘Baby-Boomers’ has a real-time dilemma right now.

The fact of the matter is that through their steadfast work ethic and continued commitment to progress, this generation is principally responsible, directly or indirectly for every aspect of economic prosperity and growth both here and abroad.  No single generation has accomplished or contributed more innovation in virtually every industry.

The wealth of opportunity we all enjoy was forged on the pioneering backs and innovative minds of this ‘Boomer’ generation.  And while with the dominance of the internet, smart-phones and tablets, and the pace of innovation has indeed increased dramatically, it will be some time before these more recent developments produce the kind of real contributions and results delivered by what I affectionately and proudly refer to as ‘my’ generation.

The Dilemma

The ‘oldest’ of the Boomers are 66 years old, the youngest are 48 years old and the majority are in excess of 58 years old.  Many have left or are leaving the work force (either voluntarily or otherwise) and beginning in October of 2013, they will be reaching this critical inflection point in their lives at a rate of one every 8 1/2 seconds.

This generation is uniquely different from previous generations in that they will tend to live an additional 30 to 40 years post retirement. Unfortunately, the vast majority of them do not have sufficient financial where-with-all to live out the remainder of their lives without an income of some kind.  While they may initially have anticipated that the capital markets would secure their retirement nest-eggs, it is clear that with the dramatic compression in the monetary value of the exchanges,  they will need to continue to earn a living of some kind.

And at the same time, with the longevity they enjoy, this industrious population intends on doing something significant, something that contributes in a meaningful and rewarding way, while also earning a living doing something they’ve always wanted to do…something they love to do.

They have ample skills (they know more useful stuff than most non-boomers in fact). They typically have sufficient resources to make a good go of it IF they don’t waste them on trial, error and guesswork trying to build the wrong business.  And by their very nature,  once they commit to an outcome, they are powerfully motivated and dedicated to achieving it.

And if that were all there was to it, there would be no dilemma.  But it’s not.

The Problem

The problem is that because they have invested themselves so extensively in jobs and careers throughout the last 3 to 4 decades many:

  • Have lost touch with their individual strengths and HOW to organize their lives around them so they can invest the majority of their time doing what they love.
  • Have not developed the entrepreneurial skills necessary to succeed in a building and growing a business and will tend to habitually fall-back on previously used career methods; which are usually the wrong approach.
  • Have formed and are constrained by deeply entrenched mental models and (limiting) beliefs about what is and is not possible for themselves; what they can and cannot accomplish; and what it takes to succeed in business.
  • Have no idea how to go about finding, validating and growing a business that they can be successful with and will tend to freeze with uncertainty as a result; which is a fatal error in business

Let’s face it; it’s challenging enough to succeed in business even without starting from a deficit like this.

And the likelihood of success diminishes quickly with it; even if you’re not a baby-boomer.

The Solution

So here are four things you can do (whether you’re a boomer or not) to maximize your success potential and get hard wired for success:

1. Know HOW To Leverage Your Unique Advantage

Knowing your strengths is, without a doubt, an important step in the process. Whether you use the Entrepreneurial Strengths Assessment I’ve provided or some other assessment instrument, you need to be clear about where you’re most capable and talented and where you’ll tend to have blind spots that could sabotage you.

But just knowing your strengths is not enough.  The fact is, you are likely ‘good’ at doing something (a strength) that you really don’t “like” doing all that much.  And if you tried to build your business around something you don’t like doing, besides being completely miserable each day, you simply won’t be able to sustain the mental focus and effort necessary long enough to succeed.

So it’s not just about strengths.  Your choice also needs to include a dimension of passion and enjoyment in order to form the basis for your unique advantage to get real traction.

Once discerned, you’ll need to organize your efforts so you spend the majority of your time where your contribution has the biggest impact and retain the support of others to handle the things you are less skillful and talented doing.

2. Know WHY Your Building Your Business

The bottom line is that you’re going to invest a lot of yourself (time, energy, commitment, etc) in building a successful business.  Unless you have a clear, concise, definitive and deeply entrenched motivation for doing what it takes, you will ultimately give up or fail.  There is no way to ‘fake it til you make it’ in the entrepreneurial game.

In order to focus your most powerful mental and physical energy on producing the outcome you want, you’ll want to record your key motivations clearly and unambiguously in detailed specific terms on paper.  Instead of recording things like ‘financial freedom’ or ‘my kids’, get specific.   What exactly is the outcome you’re looking for.  Consider all areas of life when you do this. Specifically what do you want your business to deliver in terms of money, time, relationships, recreation & fun, personal development and community contribution and so forth.

3. Know your “exit” strategy

You’ve heard that old saying about “beginning with the end in mind”, right?  Well it couldn’t be more true than in the case of building a business.  Building a business without a strategic exit plan of some sort is nothing more than creating a low-wage-long-hours job.  Think about it.  If all you’re doing with your business is growing just enough cash flow to pay your expenses and withdraw a paycheck (even a big paycheck), then why do it?  The true “value” of your business is in the “exit”.  And your “exit strategy” will determine what decisions to make and what actions to take as you drive and grow the value of your business.

For example; lets say you decide that your ‘exit strategy’ is to leave your business to your children so they can enjoy the leveraged cash-flow you’ve created through your sweat-equity.  Then clearly one key driver for the value of that business will be continuity or recurring cash flow (as opposed to intellectual property or hard inventory assets) .  As a consequence, the decisions you’d make and the actions you’d take would primarily serve to maximize cash flow.

Any exit is a legitimate one; sell the business, IPO (a special case of selling), gifting, etc.  You can even change your exit strategy at will.  But one of the most important key driving factors for your success is having, knowing and managing your business to a defined exit.

 4. Have a “mind set” and “skills” development and support plan

People fail in business not because of any lack of desire, commitment or a scarcity of effort. Rather, they struggle because they don’t command the key success skills and thinking resources necessary to achieve their success goals.” (Steve Little)

If I’ve learned anything at all in the 4 decades I’ve been in the entrepreneurial game, it’s that your success is going to be determined by what is going on between your ears far more than anything else you “do”.   No innovative new product, clever marketing scheme or slick sales presentation will produce a substantial result if you don’t master the psychology of success and invest in developing the skills and habits that equip you to create a winning outcome.

No matter how knowledgeable or experienced you believe you are, your success will ultimately be determined by how effectively you grow and develop your mental capacity to succeed.

I pointed out previously that the rate and magnitude of your success is a directly proportional to the quality of the decisions you make and the velocity of the actions you take. Your decisions however are governed in large part by the mental models and beliefs you hold to be true about what is necessary to succeed.   If your world view is such that your success is governed by certain conditions or circumstances, then you will either reject or fail to see any opportunities that may exist for you outside of them.   You will literally not “see” an opportunity that will launch you into the success stratosphere and will instead continue to struggle and suffer in frustration.  You’ll literally be stuck within a mental model which disallows your advancement, achievement and success, unable to break free.

On the other hand, if you’ve developed the necessary ‘thinking-skills’ to dis-assemble these models and eliminate the beliefs that don’t serve the outcome you desire;  If you know how to ask and answer the right questions at the right time;  if you know how and where to look for new possibilities and generate creative and innovative options; If you have the skills necessary to verify the viability and assess the risks associated with each option; and if you’re equipped with a disciplined decision making practice, then you’ll be in a position to claim a commanding advantage and win big.

Once mastered, you’ll want to continue to develop these kinds of skills further and surround yourself with the people and practices that serve you and the achievement of your goals and objectives.  Entrepreneurship and business ownership is a dynamic discipline.  What worked today will eventually not work tomorrow.  As I outlined in the post “Beware The Five” you’ll want to surround yourself with people who are ahead of you or further along on this growth and development path.  The more time you spend learning and growing with them, the more success you’ll enjoy and the easier and more consistent it will become.


Frankly, these 4 elements are not unique to the ‘Baby Boomers’ at all. The distinction I offer relative to the ‘boomers’ is that, in general terms, while they are further along the journey and have accumulated powerfully valuable wisdom, they also tend to carry more constraining mental baggage that they must learn to master before they’ll achieve all that is truly possible for them.

That said, these ‘success principles’ as well as dozens of others I teach people in my various coaching and advisory programs are fundamentals ALL entrepreneurs, regardless of age, must master in order to realize all the success available to them.   Whether you’re a “Baby Boomer” or not, put them to work in your daily activity plan and you’ll significantly increase the odds of your own astonishing success.

ThePerfectBizFinder Program is a “home study” system proven to reveal not only the best business for you, but also how to organize that business for the best possible outcome.  In it you’ll not only get a step-by-step blueprint to creating a business that truly delivers the lifestyle and financial rewards you want, but you’ll also develop the “thinking skills” and disciplined “success habits” so vital to your success results.  Whether you’re just beginning to create and consider options, whether you’re an upstart newbie or a seasoned veteran business owner,  ThePerfectBizFinder Program will help you develop the skills you need to succeed and achieve the most lucrative and rewarding results.

ThePerfectBizBuilder Program expands on these same powerful success building principles, methods and techniques and is delivered with the advantage of ongoing one-on-one support from a dedicated business building success expert. We literally roll-up our sleeves and, through a program that is custom tailored specifically for you and your needs, escort you through the entire process each and every step of the way and guarantee that you build the wildly successful business of your dreams.

Don’t forget to ask me about my brand new “Office Hours” Program in which you can get direct access to me 1 to 2 times each month for advise, innovative breakthrough strategies and tactics and ongoing coaching and support.  Ask me about it in the comment block below.

Be sure to let me know what you think about this post.

I’m standing for all that’s possible for you in life and business.





{ 3 comments… read them below or add one }


Thank you for taking the time and putting out this worth while information. your information is right on. You break it down simply and meet up with criteria for the business minded as well as myself who is more of a lifestyle entrepreneur. I appreciate your ability to cross all those barriers and reach various types of thinking. I learn so much from your work — thank you!


Pat Wooldridge

This post is so accurate, and I think it is invaluable information. I’m 4 years beyond Baby Boomer. I look at my brother, 5 years younger than I, who at a young age saw a need for a particular business. Used parts for Caterpillar machinery weren’t always easy for the owners to get. My brother, working as a garage mechanic, decided to begin a distributing business. In a matter of a few years he left his mechanic’s job so as to devote the needed time to his ever-expanding business which continues to this day. I believe he now has 2 warehouses, his son works with him, and they have a full time job (on their own terms—enough time off; vacations, etc.) and work together well. They like what they do.
At a young age he made many mortgage payments at a time on his home, quickly paying it off.
You are so right, Steve, when you say that people must love what they do, feel satisfaction in it, and have plenty between the ears so they can plan their working future so that they don’t have to work themselves to the bone. Bill has done this, and continues to, and I’m proud of him.


John Sawyer

Hi, Steve,

Being a Baby Boomer myself, what you’re saying resonates with me. Point 4 is especially true and this is where I’m finding the journey the most challenging. I’ve been working on building an online business for the past 5 years or so and only within the last year or so determined what it is I enjoy doing and can bring to the table to help others, which I believe are two very important keys to success. That has produced more and better results so it’s a matter of continuing to get rid of the old mindset to make further progress.

I’m looking forward to more of your insights.




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