Live Better, Retire in Chunks

The year I turned 50, It’s safe to say I finally felt like an adult, no longer an 18-year-old trapped in an older body, and it feels good. Life is a raucous affair where we spend most of our time trying to make sense of it all. We live in a world where most of us stand perpetually in front of a fire hose that gushes responsibility, opportunity, and challenges. The good news is that by the time we hit middle-age we’ve come to terms with what it’s all about. There are no simple paths; there are no simple choices just the objective of putting one foot in front of the other, so each day becomes more enjoyable than the last. Taking command of one’s self is the gift of middle-age. It’s very powerful to have a clue; it’s very powerful to look upon one’s life and see the connectedness of all of the random that has brought us to where we are. Relish that; it’s hard earned and well-deserved. Wisdom is the currency of middle-age and wisdom is the compass that guides you forward.

Those gray hairs and those wrinkles are our badges. They are the proof that we have put in the time to get an understanding of what it’s all about. Now, of course, this is an ongoing journey it only stops when we stop. Science tells us that there is a U-curve that denotes the satisfaction people have with their lives. Unfortunately, from around ages 45 to 55, that curve tends to be at its lowest. It’s probably the reason that by the time we hit middle age regret tends to creep in and muddle things. The good news is that once we take stock of midlife challenges that satisfaction curve heads back up. The amazing thing is by the time we are on to the last chapters of our lives our happiness will likely exceed that which we felt in our 20s. So if middle-age has you, navel-gazing, don’t panic, it’s the cost of maturity. Circumstances hands people a midlife buzz kill in the shape of the satisfaction u-curve, and I say rage against it. If the curve sucks, shift it. Retiring in chunks is a way to mess with that curve.

We live our lives in a series of events that revolve around education, career, relationships, children and ultimately retirement. On paper, it looks nice clean and easy to do. In reality, midlife is when many people start to wonder if that path was more bait and switch than realistic plan. The traditional path is manipulative. It tells us to work hard, do whatever everyone else does and enjoy your rewards in retirement. Where have we heard that? Struggle in this life, be rewarded in the next? I’m too much an existentialist to believe that is the most appropriate path. The idea that you stay in the box toiling away until the magic age of 65 when you suddenly get to live again is utterly insane. Life is for living with energy and determinism. Time and tide wait for no one, ever.

The question to ask is what is retirement? For many, it’s the idea of growth, the idea that you finally do all the things you wished you were doing right now. The challenge is that if you play by the rules by the time you retire, you may be mostly dead or at least so overwhelmed with the change you can’t think straight – or as happens all too often simply drop dead because of the stress of it all.

It’s the money thing that tends to mess people up. Most people have no idea how much money is enough for the life they want to lead. Unless you treat money as a tool to be used strategically and with purpose, you will never have any; it’s just too easy to waste. Now most people can’t throw their arms up and say to hell with it I’m out of here at midlife, but you can take moments of pause for growth now while you’re still young and that’s the core of retiring in chunks.

Waiting for the right time to live your life is the wrong way to think about life. Things can change on a dime. In our 20s we are invincible and immortal in our 40s, 50s and beyond, we know better.

What is this retiring in chunks thing? Well, it’s not a vacation its an immersion. It’s taking 2 to 4 months and living differently. For me it means trying new cultures, meeting people while remaining connected with both my career and those I adore at home but giving myself the chance to be surprised. Dissatisfaction in midlife amplifies when it feels like things are just repeating over and over. Retiring in chunks is seeking something more dynamic than sitting at the pool bar. The only way to regenerate is to seek the new. When we put ourselves in new situations, we face challenges, and from the challenge we get the gifts of both surprise and courage. Surprise and courage are the spice of life but as we get older managing life starts to feel like living an algorithm. Some people like living life as an algorithm, I’m not one.

I make my living as a member of the creative class which means surprise is the lifeblood of my career. To be good at what I do, I need to be in front of a firehose of the different so that I can see possibilities. Many of the challenges of midlife tend to close the valve on that firehose. Retiring in chunks is a way to turn it on with gusto.

It’s time to put away the bucket list and replace it with a must-do list. Taking the time to find the things in life that most engage and energize you is essential especially at midlife. The easiest way to put midlife regret into the rearview mirror is to replace it with the adventurous spirit of midlife possibility.

Millennials don’t get to have all the fun.

Unless you’re a wage slave trapped in an awful game where you have no self-determination retiring in chunks should be a real possibility even if you have a complex family life. There are many places in the world where you can go and have a much richer lifestyle for less money than you can in Canada or the United States. It’s a form of lifestyle arbitrage where you can buy better and cheaper somewhere else. You owe it to yourself to give it a look.

I’ve retired in chunks a few times in my life, and every time I have I come back with more vigor and more possibility than before I went. Re-experiencing the world has been the secret of my success. It’s when I don’t appreciate the transformative nature of experience is when things get dull, and my creative spark misfires. Imagine the possibilities, imagine the control and the energy that this could provide. Besides, who doesn’t want to be semi-retired at 50? The secret to all of this is managing your financial burn rate (just like real retirement it’s a good idea to experiment with fixed spending), appreciating your skills and knowing what makes you, you.

Like many of you, my working life is in the cloud. I work on many projects, and sometimes I go to meetings, but most of the time I’m working on self-imposed deadlines. I gave up corporate gigs and titles many years ago – been there done that – money and purpose trumped ego gratification for me. Now I do what I want and what I want tends to be both more lucrative and interesting because my heart is in it. I think in the last year I’ve had less than 20 meetings where I’ve been in an office. In fact, many of the meetings I have are video-conferences as traditional offices become old school.

I make my living dreaming up new things, designing opportunities, telling stories, creating strategy and managing investments. The truth is I can do what I do from anywhere. The odds are many of you can do the same. When I need a formal space to work, I head to a coworking spot and get my structure fix. There are only three things that I need to be successful professionally, and they are maintaining connections, continuity, and contribution within my business relationships, and it doesn’t matter where I am to do that. What does matter is having a clear idea of who you are. It’s about understanding how your value fits into a version of yourself anchored by the desires, skills, and aspirations that work best for you. Knowing who you are makes it all much easier. Rather than being identified by a career or a title being identified by the value you create opens more doors. Once you know, what your unique approach is regarding your abilities the world gets much more interesting. The grass is always greenest where you water it. Knowing what the grass looks like could be the greatest gift you give to yourself.

As you read this I’m sitting in Portugal, Lisbon to be exact. It costs me less to live here than it does in Toronto (I’m practicing lifestyle arbitrage), and it’s probably around 20° warmer. So, while I’m still creating and fostering my existing ventures, I also have another job during my chunk of retirement and that job is to learn. Part of the point of taking a chunk is to sharpen the saw as Stephen Covey put it. I’m here to see new things, meet people, make connections, learn a different language but most importantly gather new ideas and insights that make my business stronger. Retirement in chunks is me in R&D mode. When life is in perpetual repeat, it’s harder to come across new ideas and the truth about life in the creative class is that it requires new ideas and new perspectives all of the time. Like I’ve said retiring in chunks is my secret weapon for both living life how I want and maintaining and growing my competitive edge.

Retiring in chunks lets me test the waters of what I may want in the future. It’s a form of future proofing my happiness, expectations and evolving my competitive advantage all at the same time.

Take a moment and look at your situation and imagine if you could start retiring in chunks and stop waiting for someday maybe, change your someday into today…