With the emergence of the COVID-19 pandemic, and the ensuing rise in unemployment, many are contemplating whether to start their own business.  Certainly, being self-employed has a certain appeal.  However, the two pivotal questions anyone should ask before going it alone are: 1) Do they have the requisite temperament and personality to become an entrepreneur? and 2) What can one reasonably expect?

A Long and Winding Road

I started my own coaching practice in July 2015 after leaving corporate life.  While I didn’t come from a family of entrepreneurs I like to think I had an entrepreneurial streak hiding deep inside of me.  As a high school student I started my own business cleaning houses, cleaning windows and gardening.  That same summer I was hired by my church as a janitor when the regular employee went on an extended vacation.  A few weeks later I was hired by Ford Motor Company to work as a summer student relief operator on their assembly line in Oakville.  At one point I had six different jobs going.

During my career I often wondered what it would like to be self-employed.  During the latter stages of my career I found myself increasingly bored with the routine of commuting into Toronto and doing work that, over time, was neither challenging nor energizing.  The thought of being my own boss was appealing as a lifestyle, but I was concerned about the financial risks associated with working independently.

About 2013 I started exploring the idea of becoming a Career and Executive Coach and a Human Resources Consultant.  I did my research, talked with professionals in the field, and in early 2015 made the decision to start my training through the College of Executive Coaching in California.  In mid-2015 I was laid off from my position two years shy of being able to take early retirement.  I accelerated my coaching training, started my own company, and marched full steam ahead.  I secured one contract, and then another.   In June 2017 I received my ICF certification, and over the course of the pas three years I partnered with various organizations through which I now provide coaching and Human Resources services.


Self-employment can be exciting but it also carries with it many challenges (Photo courtesy of Christina Morillo from Pexels)

The Good, the Bad and the Not So Great

So, what worked?  Here, in retrospect, is what I believe I did well:

  1. I planned my launch.  I took the time to attend meetings on how to establish a business.  I wrote my business plan, had it critiqued, and used it as a guide to build my business.
  2. I defined my coaching niche.  I knew I wanted to coach professionals in transition and executives.  That was my focus of concentration.  I make no claim to being able to coach parents with problem children, persons with mental health issues, or those seeking guidance on nutrition.
  3. I didn’t overextend myself.  I managed my time well, and tried to allocate time off to re-charge my batteries.  I know when to commit, and when to defer or postpone.
  4. I made sure I got the requisite training. I have spent a small fortune in taking courses, gaining certifications, and learning new skills.  The amount of money I have spent in the past five years on furthering my education would be enough to buy a high end German luxury automobile.
  5. I networked like crazy.  I went to numerous meetings in the hope of meeting business professionals and finding ways of promoting my services.
  6. I made sure I delivered value.  I went over and above what I needed to do in order to help my clients.  If that meant giving away services for free or being available after hours or on weekends I did so.
  7. I pivoted where necessary.  I realized after a short time that despite the value of coaching many people, reluctantly, aren’t willing to pay for it.  Many will think nothing of dropping $500, $600 or $1,000 on a suit or dress, but ask them to invest in themselves and many balk at the idea.  They keep doing things over and over again rather than investing some money to learn techniques on how to do it properly.

In light of this what did I do?  I pivoted.  So, in addition to offering my services to individuals I also now offer them through other organizations with whom I have established effective partnerships.  I also recognized that coaching can function in the virtual space just as well as in person or by phone.  Zoom has become a critical part of my business.

I always wanted to teach, and in 2018 I landed my first part-time teaching assignment.  That was followed with another in 2019, and still another this year.  I love teaching, and sometimes I wish I had pursued my dream of becoming a high school History teacher after graduating from university.  Besides providing another source of income teaching gives me an important outlet to connect with young people that I really enjoy.

On the flip side, here’s what I didn’t do well:

  1. A website doesn’t guarantee you clients.  I developed my website in 2015, and have revised it three times since, most recently last month.  My website promotes my services but it alone doesn’t guarantee me clients.
  2. I spent way too much time kissing frogs.  As mentioned earlier, I joined a lot of professional organizations, visited many trade shows, and attended a number of public functions and business meetings.  In retrospect, most were a complete and utter waste of time and money.  I should have chosen with greater care which ones to attend.  My advice?  Use discretion.  There are lots of networking groups out there, everything from Meet Up Groups to Chambers of Commerce to service organizations.  Some are useful, but sadly, most are not.  As a business owner I realized belatedly that I don’t have time to spend in two hours luncheon meetings.  
  3. I should have asked a lot more questions.  I received countless invitations to join groups or participate in forums or events.  I willingly accepted virtually every one without thinking how this would be a useful networking or business promotion function.  They weren’t.  If I had to do it again I would have asked a lot more questions at the outset.
  4. I should have negotiated more aggressively.  Every service provider has an official price, and then there is their “bottom line”.  Finding the sweet spot between these two is where I should have landed.  If you don’t ask you don’t get.  There is also power in remaining silent and holding off before committing.

A Final Thought

The transition from employee to business owner has not been easy.  There is a security associated with being an employee that simply isn’t there when you start and operate your own business.  In my case, I have an advantage in the sense that I have support through my pensions and my teaching.  Without it I would be much more exposed and at risk.

I’m 66 and have no intentions of slowing down or retiring.  Someone the other day asked me if I had to do it again would I still do it.  The answer is an unequivocal “yes”.  As a business owner I view the world differently, and am much more cognizant of my time and the services I provide to others.  Being self-employed has made me a better person and tested my resolve in ways I never thought would be possible.

The one thing I would tell anyone contemplating starting their own business is this:  everything takes twice as long to complete as you might expect, and is three times more expensive than you forecasted.

The other thing I would suggest which perhaps is more important, is to seriously explore your options before launching.  Write a business plan, and commit to paper what it is you will do, how you will do it, and what you are prepared to initiate to make it a success.  Then, get a trusted business professional to review and critique it.

In short, look before you leap.