​​​​​​​Should You Pursue a Second Career or Retire? By Robin Trimingham

Should You Pursue a Second Career or Retire? By Robin Trimingham

As those of you who have followed the development of Olderhood already know, our company first started when my business partner decided to accept an early retirement offer from his employer at the time. Being a qualified Scottish CA and experienced consultant in the banking and reinsurance sector it had seemed reasonable to assume that he would easily transition from fulltime employment to doing project and consulting work on a fairly regular basis.

However, while there was work available, it proved harder than anticipated to fit into the positions that others were looking to fill.

Either the company wanted someone full-time, or there was a grueling travel schedule, or the pay was not commensurate with what a seasoned executive might expect. Everyone was pleasant and many nice lunches were exchanged but the work did not materialize.

The message was clear – embark on a second full-time career (possibly involving scaling the corporate ladder all over again) or retire for good. It was a rude awakening.

Undaunted, however, my entrepreneurial partner was not of a mind to give up. If the dream job was not going to materialize from the traditional job market, why not just sit down with a piece of paper and dream one up?

Many crumpled pieces of paper later … the phone rang.

“I’ve got it!” he declared, “I’m going to start a blog about what’s been going on and figure it out as I go”.

“Great!” I replied, “I’ll help”.

Five years later Olderhood has taken root and our business is growing both here on island and in North America and the UK where we work with companies and strategic partners on a variety of coaching and consulting initiatives.

If we had it all to do over, however, would we have given more thought to what sort of business we wanted to start and what it would take to convert our innovative ideas into a sound business plan? Yes, I believe we would have.

Based on our experiences, the top ten things to consider when contemplating embarking on a second career when you leave your current place of employment would include:

  • Think long and hard regarding whether you most want to pursue consulting, work for someone else, or start your own business.
  • To pursue consulting or a job with someone else, research and investigate your options and try to line up your “next gig” before leaving your current job.
  • Research which certificates or qualifications you might need - and complete these before making your move.
  • Be realistic regarding how much time you want to devote to this second career and discuss your plans openly and thoroughly with your life partner.
  • If you want to start your own business, thoroughly research any potential competition that might exist and think about how you will differentiate your skills, products and services from theirs.
  • Also consider what “niche” your business idea fits into and research who can assist you with potential networking contacts and sources of business referrals.
  • Research all of the costs involved in starting your own business as well as the amount of time it will take to complete company formations, open bank accounts, etc.
  • Give careful consideration as to how you will publicize your business or service and how you will get your first customers so that you can generate some endorsements and positive reviews to show others.
  • Be prepared for a second career or start up company to evolve at a different pace (and in some very unanticipated ways) from your original career and be open to being adaptable, patient and endlessly innovative as you progress.
  • Only involve yourself in work, projects or initiatives that inspire you and bring meaning to your life and the lives of those you serve.

By Robin Trimingham


Bill Storie and Robin Trimingham are the co-founders of The Olderhood Group Ltd., an online learning company with + 100,000 global followers in over 100 countries. The Leaders in Action video series, produced by Olderhood Productions International (part of The Olderhood Group) features short video interviews with recognized Leaders in multi-national companies, global organizations, and renowned experts in various locations around the world including London, Los Angeles, Mumbai, Singapore, New Delhi, and many others. The Series is published on Olderhood’s social media pages, The Royal Gazette, LinkedIn and through its several Partnership Networks globally to millions of viewers around the world. The Olderhood Group provides life transition, financial literacy and retirement lifestyle planning, education, and training for corporations in the form of videos, podcasts and webinars. The consulting practice focuses on helping companies augment their employee benefits programs, and their customer outreach initiatives, by seamlessly integrating customized workshops, in-house training, and online learning opportunities into their existing platforms.