4 Tips and a Self-guide for Rebranding “Retired” Executives Seeking to Start a Business or Reinvent Themselves

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Want to start life anew in your 60’s and above? – 4 tips for rebranding retired executives and your new companies.

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I recently had the privilege of rebranding some highly accomplished senior executives who retired from top consulting firms or multinational corporations. They are baby boomers in their 60’s and above, all in great physical and mental shape. To protect their privacy, the following is only a generalization based on their collective identity. 

A few months into their retirement, they realized that full retirement, completely detached from the working environment does not fit them. They miss their prior leadership roles, decision making, teamwork, actions, challenges, esprit de corps, accomplishments … They want to remain relevant and influential in the thick of today’s fast changing world. Some of them want to prove to themselves that they can still accomplish things and realize dreams. 

Starting life anew in your 60’s and above

There are plenty of role models around: the 81-year-old President Biden is running for re-election against the 77-year-old Trump, and the former House Speaker Nancy Pelosi is 83 years old, still going strong in Congress. The founders of Snowflake when it went public were all in their late 50’s.  Being 60 and above today is becoming the true prime time of life, after acquiring wisdom, experience, financial security, and lessons from the school of hard knocks. A lot can be accomplished in their next 20-30 years. 

If you are one of the gray-haired but young-at-heart, before you jump in with both feet into a new business, it is important to go through these steps first:

(1) Is growing a business, or starting a new career the right thing for you?

Many of the “60 & Uppers” decided to be their own boss upon a rational assessment of the corporate world. Some of them even flirted with seeking C-suite positions in large companies, only to find out that the odds are stacked against them due to ageism and other entry barriers. They also harbor a distaste for not having control over the corporate culture and structure.

So, they either buy a company or start a company, to run it the way they envision. 

After working closely with a number of these “Type A Retirees” to rebrand themselves and their companies, I came to appreciate their unique persona, needs, wants, and goals. I also detected a pattern they all share in common, such as:

  • Possessing wisdom, experience, leadership (but their expertise may or may not be relevant to their new business),
  • Desiring to run their own show, be their own boss, grow their own business or consultancy,
  • Having a commanding vision, thanks to previous leadership roles in large companies,
  • Wanting full control over their own destiny and their own companies,
  • Being driven by desire for accomplishment, financial rewards, and a wish to leave a legacy.

If you share at least some of these traits and you are thinking about starting your own company in your retirement – acquired or built from scratch – the next question is: 

(2) To what extent do you want to work during retirement? 

The next question facing the “60 & Uppers” wanting to reinvent themselves and run a business: Do you want to be ALL IN? Or do you just want a “retirement hobby”?  Is it possible to grow a successful business AND enjoy retirement life at the same time? 

The short answer is: It depends. You harvest what you sow and you get what you invest in. But it is very hard to grow a successful business with only partial engagement, in my opinion.

To help you find out where you are on the spectrum of commitment or “seriousness”, and the  level, scope, and depth of your post-retirement career, consider factors such as:

  • Your tolerance level for risk and stress,
  • Your family support and personal comfort zone, 
  • The amount of leisure time you want to give up to deal with the daily challenges of running a business,
  • How much time, money, effort you want to invest in building a company,
  • What you expect to get out of your business, 
  • Your goals for business, career, personal life, and financial success.

(3) What does “success” or “failure” mean to you?

All these retirees from the corporate world face the same challenges in making a paradigm shift from a large corporate mindset to growing a small business or a startup. Like everything else in life, not everyone succeeds at everything.  At the outset, it is important for your own mental health and your family relationships if you prepare for the worst, strive for the best, and get your loved ones on the same page. You need to know about potential losses and gains, before you start:

The “worst”:  A failed business, at the cost of not enjoying a retirement life (however you define “retirement” – having hobbies, being a grandparent, or doing nothing: is being a couch potato better than trying a business and failing?)

The “best”: A thriving business of your own making, a successful new career, OR a full and happy retirement life without working, by choice – again, you can’t have “the best of both worlds”: a successful business and full enjoyment of leisure.

The “neither worst nor best”: A just-ok business (not thriving), and not fully enjoying leisure.

Nothing is per se a “failure” or a “success”, since the definitions are subjective and personal to each individual. 

After evaluating all the above, If you decide to start a business in retirement, the fourth question is:

(4) Where to start? – Rebranding your new company starts with rebranding yourself

First and foremost, lay your foundation right, so the skyscraper can grow tall and straight; otherwise you end up with a Leaning Tower of Pisa. 

Our 10 years of helping business and personal brands decode brand DNA with deep diving and heavy lifting proves this point: only upon a solid foundation can a brand – business or personal – be positioned, built, and thrive. 

Then and only then, can the brand essence be distilled into its name, a tagline (if so desired), and a logo which is the visual manifestation of what a brand stands for. 

Afterwards, the brand structure and strategies can be built, upon which hang the brand stories, narratives, and messaging.

The verbal and visual content will then be designed into a brand’s website and other media. 

  • A brand is not a result but a vision, a process, and a starting point. 
  • A brand is more than a merely successful business.
  • A brand is the guiding light, the destiny, and the purpose for a leader and for a company.

Anyone is his/her own unique brand.

Any company, no matter how small or large, is its own brand. 

Build a brand to start right, not just because brand equity multiplies EBITDA at least four times upon exit, but also because it is the culture, legacy, and unifying power both internally and externally.

Even if, in the worst scenario, your company “fails”, you have lived up to your purpose and your vision, in pursuit of your dreams. Nothing is wasted.

And it all starts with decoding the founder and CEO’s own personal brand, that will lead to the success of your new business brand.


10 Plus Brand is a multiple award winning agency, known globally as a leading brand-building and brand-marketing, full service digital agency. We decode brand DNA with our proprietary process, create brand structure, positioning, go to market strategy, messaging, and storytelling, and amplify with content, SEO, website, videos, social media, and high authority blogs. Please contact us for more information.

© Joanne Z. Tan  All rights reserved.


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