Learn to Play The Long Game

Today’s article is the first in a series written by Simon Chan who started his own VLR earlier this year after working for 20 years in the financial services industry. He has a broad base of experience with the subjects of pre-retirement and financial independence having worked in multiple businesses such as banking, wealth management, insurance and group retirement benefits. Most recently Simon was the head of business strategy for the Canadian Retail Business for a global insurer. In his role, he became interested in how technology, globalization and the rapidly changing environment is impacting the lives of millennials. In short Simon knows his stuff, is a great guy and wants to help.

I believe it’s important that we understand the new challenges that will be faced by our kids and grandkids in the years ahead. It won’t be easy but we can succeed if we all work together. -Mike 


 This morning I woke up and as part of my daily routine, I began to read my Twitter feed to catch on the latest basketball news and what’s been happening in the world. Over the past several weeks, I’ve seen several articles on the rapidly changing workplace with the entry of new technologies like artificial intelligence and machines learning. This got me thinking about the “Big Dip” article that I read on the   Victory Lap Retirement blog and whether Millennials who are in the early stages of their lives will experience the “Big Dip” in the same way as the Boomer generation.  

The Early Years (A) 

When I think of what Millennials are dealing with early in their lives and careers my belief is they are facing a much more difficult road than Boomers. Millennials are entering a globally competitive job market which has made post-secondary education table stakes resulting in students taking increasing amounts of debt. In addition to the pressures of school and finding an entry level job to begin the process of paying off their student debt, Millennials are bombarded with marketing messages encouraging them to spend and buy new products. No wonder we are seeing the incidence of anxiety, stress and depression increase in university students and young adults. They feel paralyzed and in constant stake of anxiety. 

The Valley (B) 

Both Boomers and Millennials enter their 30s/40s with increasing levels of responsibility which starts them down the big dip as the mounting obligations of getting married, growing a family, buying a home begin to reduce their financial flexibility and overall freedom. However, Millennials today are entering their 30s already behind the proverbial “8 ball” with higher levels of student debt, historically high housing prices making housing almost unaffordable, and an uncertain job market. To make matters worse, most Millennials will not have access to traditional financial building blocks such as a defined benefit pension plan that provides a guaranteed retirement income stream leaving them to decide how much to save and what investments to choose. This has led some Millennials to reject the path their boomer parents took and consider non-traditional paths such as not having children, rejecting the notion of buying a home, and taking more of a minimalist approach to life.  

The Bumpy Climb (C) 

As Boomers reached their late 40s and 50s, they began to experience more freedom as their children moved out of the home, their incomes began to rise, and financial obligations were declining. For most of their working careers, Boomers had stable jobs and a good pension plan to rely on in retirement. As Millennials reach a similar stage it their lives, the world will not be as stable and constant change will be the new normal. The constant change will result in the need to consider relocation to find work, going back to school to re-skill to remain relevant, and other working models such as freelance and being an entrepreneur. This stage will require Millennials to make multiple life transitions which will create stress both financially and emotionally. This creates questions like how will a Millennial fund these multiple life transitions and will they need to dip into their “retirement” savings. Will Millennials have the resilience to adapt to the ever-changing environment? 

What does this mean? 

My belief is that the Millennial version of the “Big Dip” will be much more challenging than the ones that Boomers experienced. Their journey to higher levels of freedom will be slower than the Boomer generation and will require more life transitions. This means the traditional path to success that the Boomers took is no longer relevant for Millennials. Millennials will need to find a way to play the “Long Game” and develop a new agile approach to maneuver in their constantly changing world.






Share this:

6 thoughts on “Learn to Play The Long Game

  1. Tawcan Reply

    Very interesting about the big dip, I guess I’m going through that myself with getting more responsibilities at work and now two kids at home. But I think it’s really how you see the situations and how you react to it. If you think negatively, the big dip will create a lot of chaos for you. If you think positively and see the big dip as one of the many challenges in life that allow you to improve yourself as a human being, the big dip will probably create a lot of great opportunities for you. It’s all in the mind set. 🙂

    • Mike Drak Post authorReply

      My only regret is that I didn’t know about the big dip and the concept of FI when I first started out. If I had I would have probably achieved FI much sooner than I did and avoided a lot of stress along the way. The big dip is a big trap for some people as they are unaware of the long term cost of their chosen lifestyle. You on the other hand know what you need to do to get out of it quickly and are taking the required action. Prolonged exposure to high stress can really mess a person up. Great to see that you are showing a lot of people the right way to deal with it.

  2. Matt Reply

    Great article, Simon!! It all makes me curious how the experience of boomers and millennials stacks up against the many generations before them both. We all tend to be chronocentric in our analysis of demographics, but I wonder whether the post war boomers are an abherration, and the less linear path of millennials a reversion to the mean of sorts (longer life expectancy and exposure to unprecedented technology changes notwithstanding). In other words, it would be interesting to understand when in history concepts like ‘financial freedom’ and ‘stability’ became aspirational or even normative for western society, and on what basis do we suppose they may or may not be for the longer term? And what happens once someone achieves them? Is that the end game? Great conversation… looking forward to your next post!!

  3. Simon Reply

    Thnaks Matt!

    As usual your comments are always thought provoking. Change and a non linear path is not new in human history but I think the one thing that is different about what’s happening today vs previous periods in history is the pace of change. I believe this creates a unique challenge for Millennials in how they will need to remain agile and adapt much more quickly than previous generations.

    I also believe the pursuit of financial freedom or stability are a more recent phenomenon especially on a broad societal basis. In past generations, there likely wasn’t the same expectation of leisure time and the “pursuit of happiness”. Even the concept of retirement is just over a 100 years old.

    And is financial freedom or stability the end game? I think of it as more of a building block that provides people with the mental and practical flexibility to pursue their interests but I don’t think it automatically equals happiness or satisfaction. I think having a purpose and understanding your priorities in life are required to truly design a lifestyle that creates happiness and satisfaction.

    You’ve given me much to think about for future articles! Thanks Matt!

  4. Derek Reply

    Interesting post Simon and I enjoyed Matt’s comments as well. I’m just at the start of my new journey which started with the realization that it’s all about family! I have not read Mike’s book yet but on Simon’s recommendation I will!

  5. Simon Chan Reply

    Derek – Welcome to VLR and to the beginning of a new and exciting journey. I couldn’t agree more that it’s all about family and how you deliberately design your life around the priorities that matter most. I believe that trends like globalization, longevity, and technology are disrupting the traditional models for how we work, how we retire, and how we live which will lead to more individuals choosing to create their own customized journey (like you!). Enjoy reading Mike’s book and another great read that he recommended to me was “The 100 Year Life”. I look forward to catching up when I’m back from Europe!

Leave a Reply

Your email address will not be published. Required fields are marked *