“Retiring To” vs “Retiring From”

by Richard Dri


Don’t confuse retirement with vacation. It’s important you create a plan that’s fulfilling for the long-term, and about more than just having the money.

I recently turned 60. Five years away from retirement, if you go by the traditional norm

That’s a truth I’ve learned while helping hundreds of clients prepare for and ultimately enjoy their retirement. Along the way, I’ve discovered the happiest retirees are consistently those “to something” rather than those who retire “from something”.


Retiring from” sounds like I’m leaving my job without specifying what comes after that. And from what I’ve seen, pre-retirees who retire with a vague retirement dream are often dissatisfied with the reality retirement ultimately brings. Some, sadly, even die sooner.

A lot of retirees think their best days are behind them. That from now on it’s all about simply trying to stay healthy and live as long as possible.

Personally, I prefer a long life and a fulfilled one. I can’t imagine year after year going by that doesn’t bring some form of personal improvement, whether it’s in the field of education, fitness and activity, philanthropy or family wealth, anything that means growth.

As a financial planner for the past 30 years, I believe I excel at doing what financial planners do: helping their clients:

  1. Calculate the amount of money they’ll need to retire comfortably
  2. Determine an appropriate investment strategy for their funds.
  3. Adjust their investment portfolio as life changes.


Here’s how I see my solo retirement phase:

The Plan. Step 1: What activities are you most passionate about?  Some retirees might say travelling, cooking, babysitting grandchildren, maybe starting a new business. Others might say volunteering, mentoring, cycling to keep fit and exploring  new areas.

When I asked myself, I found I have three passions:

  1. helping widows and widowers with their finances; 
  2. staying in peak fitness by cycling every province and state in North America; and
  3. where possible, helping find a cure for cancer.

The Plan. Step 2. Now, how do I turn these passions into activities?

  1. I have extensive financial planning knowledge and know what it’s like to be a widower, so I feel I can apply my professional and personal skills to build a consulting firm that offers financial planning assistance to widows and widowers.
  2. I can ride in Canada during the summer months and in the southern U.S. in the winter months.
  3. As readers know, Mary died of ovarian cancer and it’s become my mission to help, where I can with the cure for cancer, Of course, I’m not going to find the cure myself, but I can participate in fundraising campaigns and start my own charitable trust aimed at providing financial assistance to cancer research projects

The Plan. Step 3. Now put the activities in a calendar. My former 40 hours of the “work week” are now freed up. I would spend about 15 hours per week cycling and weight training, 20 hours working on my consulting business and the remaining 5 hours devoted to my cancer passion (volunteering and raising money).

That leaves me with about 56 “personal hours” in the week (8 hours of sleep a night).

  1. I’ll nourish my brain by reading, listening to podcasts and attending workshops,
  2. I will strengthen my friendship (arranging lunch dates and dinner parties)
  3. Finally, and the most important, I’ll stay involved in the lives of my three children who now live in Toronto, New York, and Denver.

Will that keep me occupied and fulfilled for 25 years? I think so, but 82-year-old me might not agree down the line. That’s okay, I’ll make new plans… because I know what steps to take.


Determining what you need to save for a comfortable retirement is a relatively simple calculation. But planning your retirement vision is a much bigger project. I suggest pre-retirees start envisioning their retirement 3-5 years prior and ensure that they’re retiring to something… not from something.

Think of it… the possibility of 25 years ahead to do whatever you want. So… what do you want to do?

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One response to ““Retiring To” vs “Retiring From””

  1. Steve Schoenecker Avatar
    Steve Schoenecker

    Sound advice and my condolences to you Richard on the loss of your wife. I know how difficult losing your wife is. My wife, Joan, died of lung cancer January 22, 2021. Retirement looks a lot different now without Joan in my life. God Bless you.


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