Some Early Stage Encore Career Observations and Recommendations


A metal toggle switch with plate reading Change and Same, flipped into the Same position, illustrating the decision to work toward changing or improving your situation in lifeBy Michael Drak

Special to the Financial Independence Hub

I started my own encore career back in February 2015;  here are some of the things you might want to consider when planning your own encore career:

Should you tell your boss you plan to leave and start an Encore Career?

Bosses can start to act a little funny after you tell them you plan to leave the company at some point in the future. For some reason they believe that you are no longer fully committed to your job and that your performance will start to slide as you focus on getting ready for your new career.

This can cause some friction, so it’s best to make sure you have the bulk of your encore job preparation completed prior to dropping the bomb, just in case. In my own situation within three months of having declared I was planning to leave I was pleasantly surprised to receive a buy-out from the company. Was it a coincidence? Who knows, but I’d rather receive a payout versus a gold watch any day, plus it provided me with some liquidity until my new business starts generating a profit.

Do as much advanced preparation as you can prior to leaving your job

My original plan was to tell everyone that I was leaving in two years and during that time learn to run a blog and start working on my retirement book. Getting bought out accelerated things. In hindsight, it might have been better to have started the book and other projects prior to making the announcement.

 Have a safety net in place so you can sleep at night

My years in Commercial banking taught me the importance of risk mitigation and therefore I made sure that my wife was fully onside with my encore plans. We would depend on her continuing income to cover expenses until my new career could earn a profit. Also, since we had achieved findependence we would not have to burn through retirement savings while I built the new business. Having multiple saving nets in place gives you peace of mind, knowing you can pay your bills until the new business starts to generate a profit.

Take time off before starting your Encore Career

I started my encore career the day after leaving my job. If I could do it over again I would take a three-month “freshening” period, which is somewhat similar to what they do with race horses after a hard campaign. This is when you get a chance to recharge and think long and hard about what you want to do next. It also gives you a chance to clean out all the old skeletons in your closet, increase your energy level, restore a positive attitude, etc. I was a little burned out from my old job and my recovery period would have been quicker if I had taken the time out. Maybe it would have reduced the degree of “Sudden Retirement Syndrome” that I experienced in the process.

Play to your strengths

This is key if you want to enjoy a successful encore career. During all those years at your previous job you developed some strong skills and if you can align them with your new career you greatly increase your chances for success. Although writing and public speaking are new areas for me I know I will benefit from my sales training, my strong network and my positive attitude. As many people have told me, writing a book is the easy part; selling it is the hard part and that is the part for which I’ve trained all these years. Funny how things tend to line up when you have a good plan in place.

Encore transitions take longer than you think

One thing I discovered is there is a good chance your original plan or business model will not be the one you finally end up with so be open to tweaking things. My original plan was to focus on helping family-owned businesses deal with succession planning. However, something inside started to tell me I would have more fun helping people plan for retirement and possible encore careers. Not a big change but I think it’s smart to listen and go with your inner voice. I always believe the best bet you can make is on yourself! Tweaking my business model took some time but now I’m in my sweet spot;  knowing that gives me a great deal of confidence.

Establish good routines and stay in balance

This is one area I am still struggling with but I’m working hard to get things back into balance. Part of the problem, I believe, derived from my old job where things were very competitive and whoever worked the hardest won. The chase was always about making more money. Now I have to continually remind myself to slow down and stop chasing the money. I find myself now working more hours than I did in my corporate job but this will change once I have finished the book. Once it is completed I will restrict my time to doing book seminars, managing our wealth management business and posting articles here on the Hub. The freed-up time will be spent on exercising, and finding interesting experiences to do with our family.

So these are my initial encore observations to date. While there is still a lot of work to do in terms of finishing a book etc. and finding that I’m working just as many hours for now as I did in my corporate job I can honestly say that I feel like a kid again, when everything felt possible.  Believe me,  that feels pretty good from where I’m sitting!

Mike Drak

Mike Drak is part of the Komitas Mastromartino Wealth Management Group at RBC Dominion Securities, based in Toronto. He is currently writing a book about some of the themes mentioned in the above blog and at the Financial Independence Hub in general. He can be reached at

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