Category: Legacy

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Entrepreneurship Gig Economy Growth Mindset Legacy Self-Actualization

The Courage to Show Up

“The courage to be vulnerable is not about winning or losing, it’s about the courage to show up when you can’t predict or control the outcome.” — Brene Brown in Dare to Lead

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Photo by Andreas Fidler on Unsplash

Human beings are creatures of control.

We crave certainty. Where certainty doesn’t exist, we’ll accept probability. As a rule, we like to know the outcome before we start.

It’s why people tend to stay in jobs that make them unhappy for years and even decades. They make a calculated trade of happiness and self-actualization in exchange for certainty.

Golden handcuffs.

Just tell me my job is secure and my wages are guaranteed, the thinking goes. Give me good benefits, a strong pension at 65, and I’ll serve you for life.

That’s how highly we value certainty and stability.

The safe life.

Sure, we all entertain dreams from time to time. Dreams of doing the extraordinary. Of making a bigger impact. Of making greater contributions in the lives of others. Of attempting the bold and ostentatious, whatever that looks like in our world.

We dream of showing up in a big way. But as long as it remains a dream, the outcome is certain — zero chance.

If All We Had to Do Was Dream

I mean, the dreaming part is fun. Put a guaranteed road map in front of me, and my willingness to show up for the extraordinary shoots way, way up.

  • Tell me that if I launch a small business, it’ll be instantly successful and cash flow positively within its first year.
  • Tell me that if I buy an investment property, I’ll be able to find fantastic tenants and the property will appreciate steadily over time.
  • Tell me that if I launch an NGO, it’ll seize the imagination of thousands and make life-changing impact in a developing country.
  • Tell me that if I become a realtor I’ll be able to sell multiple listings per month from the outset.
  • Tell me that if I start working on a Youtube channel today, I’ll have 1M subscribers in five years.
  • Tell me that if I study for the LSAT, I’ll pass the exam and be accepted into law school.
  • Tell me that if I do the research and work to write a book, it’ll become a bestseller.

Of course, none of us have those sorts of guarantees. Sure, there are principles of hard work and investment that we can rely on to a certain extent. But no guarantees.

And so we tend to be a little cagey about showing up for risky ventures. About sacrificing to make big changes. About actually showing up when outcomes are uncertain.

So we hedge our bets.

The Many Fears of Failure

The fear of failure looms large. Unpack the fear of failure, and we find other fears.

  • Fears of rejection.
  • Fears of appearing foolish or naive in the eyes of others.
  • Fears of forever losing the time, energy, and capital required.
  • Fears of social judgment — “Who do you think you are, anyway?”
  • Fears of what we would have to say to ourselves if we were forced to admit defeat.

YouTube: A Case Study

I remember when our 14-year-old was 12. For a while, he was intensely interested in editing videos. He was dramatic, creative, and enjoyed performing.

He launched a YouTube channel at the time and dabbled for a while. But I saw his concern about going all in — say, committing to weekly publishing.

The fear of low views and poor response was real. What would it say about him if he went to all this work and there was little to no positive response? Could that result be even worse than never trying anything at all?

Those questions don’t go away in adulthood. They only get louder.

Fear is Something to be Dealt With

One quote that made a big impression on me last year was this one from Elizabeth Gilbert, who writes about risk-taking in her book, Creative Living Beyond Fear:

“Fear is always triggered by creativity, because creativity asks you to enter into realms of uncertain outcome.

This is nothing to be ashamed of. It is, however, something to be dealt with.”

In 2019 I applied for a job that I really had no business getting. I lacked the appropriate experience, and the responsibilities would have been somewhat over my head, at least at the outset. But I knew the interview would be a good step, a good stretch for me. And sitting around the table with five people, thinking on my feet, analyzing my own strengths, weaknesses, ambitions, and vision was a valuable process.

I showed up. And I’m proud of that, because that’s the person that I want to be.

But I’m not finished. There’s still a ton of sacred safety in my life — spaces where I have yet to step out, take more risks, and embrace more uncertainty.

I have more showing up to do.

What it Looks Like to Show Up When Outcomes Are Uncertain

When I think about what showing up in uncertainty can look like, I think of some great people:

  • my brother Peter and his wife Shannon, now in the process of acquiring their fourth business by the age of 35,
  • my cousin-in-law, PJ, whose online startup continues to win big contracts,
  • my friend Karalee, who recently moved away from a secure job to launch a new business in a completely different field,
  • Trevor, a teacher, who designed and patented a new sport and recently wrote a novel on the side,
  • Chris, who is starting a new career in real estate at the age of 40, and
  • Jen Rao, who left a well-paying job and sold her home to live a life of mobility and remote work.

I could share more examples. But to me, this is what it can look like to step out and show up in big ways, even when outcomes are completely uncertain.

I salute this group.

What Might Have Been

It’s been said that the most common regrets of the dying are not the things they did but the things they didn’t do. The things they didn’t have the courage to try.

What might have been.

Let us not be those people. Let us not live our lives wondering what might have happened. Let’s go for it, even when the outcome is uncertain.

It doesn’t require quitting your job. But it does require facing your fears.

It requires showing up — even without a guarantee of success.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again … who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.“

– Theodore Roosevelt

Categories
Family Legacy Social Media

Why You Should Preserve Your Family History

We’re undervaluing the legacy possibilities of digital media.

Bert and Eileen Cavey, my paternal grandparents

I miss my grandparents — all four of them.

On my dad’s side were Bert (1998) and Eileen (2009) Cavey, and on my mom’s, Jim (2003) and June (1991) McAlpine. I loved these four to the extent that a kid can love his grandparents when separated by 2,100 kilometres.

All four have been gone for a while now, but I’m old enough to remember warm memories and exchanges with each of them. I treasure those random slices of personal history, even as they blur and fade with each passing year.

I wish so much that they were still around. What would it be like to sit down and discuss life with each of them today? I’d love for them to meet my wife and my stepsons, to see my home, to visit the place where I teach.

There’d be a shift from amazement to horror, no doubt, when I tell them the market value — and then the principal owing — on my Vancouver-area home. No doubt they would each have some sage advice for my family life, my career, and the career choices of my wife and stepsons.

They’d be mystified by the hours we spend interacting with screens today, I’m sure. But both my grandfathers would also be secretly impressed, I’d like to think, by the frank level of dialogue that holds forth at our device-free family dinners.

They’d likely be surprised to learn that we’ve dispensed with the once-wonder of cable TV, but relieved to see news now available from a multitude of sources day and night on YouTube.

They’d probably be bothered by the improprieties of our non-denominational church, but hopefully they’d also be pleased by the warmth of community and quality of relationships that we experience there as well.

Silent Memories

Thinking about my grandparents makes me wish that I could consume their content. I wish I could bring up their channel on YouTube and peruse their videos for the hundredth time. I wish I could scroll their Instagram feeds — stretching back to WWII. I wish I could explore their blog posts, and read their articles, and listen to their podcasts.

I mean, just to have the opportunity, the chance, the choice … to go for a drive today and play an audio selection from my Grandpa. From the cloud to my phone — quick and easy. That’d be pretty awesome.

Of course I can’t do that today, and neither can you. Because this internet thing is still, remarkably, only 25 years old.

Building Legacy is Easy

Photo by Tanner Van Dera on Unsplash

Today’s incredible ease of access to the internet gives us new options. Unlike our grandparents’ generation, we possess all the platforms and tools to let our voice be virtually heard for years and generations to come. We are free to create, design, photograph, perform, speak, and record video in ways that can be enjoyed and interpreted in perpetuity, rendered in digital qualities that withstand the degrading ravages of time.

We have the choice, the means, the power to craft and preserve meaningful digital legacies.

Many of us will say that we don’t want to. We might feel reluctant to step up to the stage, to grab the mic, to pick up the pen, to type some thoughts and hit publish.

We feel as though we have nothing to say, that we have nothing of importance or value to add to this world.

But I say that we do — we all have something to say, to create, to express. Because it’s not really about the striking quality of your ideas, so much as it is about their origin.

It’s about YOU.

Think of your grandparents. Did they feel a similar shyness about expressing their voice? They may have, and yet how amazing would it be today to explore their videos, to relive their joys and passions, to get a sense of their goals and dreams, to understand their heart and concern for others in the world around them.

It would be amazing to understand them better, and in that journey, to understand ourselves better, too.

That. THAT is the gift that the internet offers us and our descendants today. Let’s not let it pass us by.

Categories
Family Finances Legacy Real Estate

When it Comes to Real Estate, Baby Boomers Can Be Game-Changers

Formidable real estate markets position parents to help their children at little to no cost.

EnterPhoto by Breno Assis on Unsplash

My Story

My parents have always been careful stewards of resources, and it allowed them to do something incredibly important in my life.

In 2006, they gave me a financial gift — one in the low five-figure range — as a down payment on a house. I was 27 at the time.

The house was not great. It was over 100 years old and situated in a run-down neighborhood. Regular drug transactions took place in the back alley.

But it was a house. And my name was on the title.

In 2015, after a move to the west coast, a refinanced mortgage, a failed marriage, nine years of semi-successful long-distance landlording, and a recent wedding, I finally sold the home.

Once the dust had settled and I paid all related expenses, the sale netted me and my bride about $40,000. Not a huge profit, by any stretch.

But using this little chunk of change and an unsecured line of credit, we were able to squeeze our way into a detached home in suburbia.

At the outset, our equity position was awful — we actually owed more to lenders than the entire purchase price of the home. I break down those figures further in House Poor and Loving Life.

But the point is that we were in a home. We knew that with two steady incomes, we could begin the process of chipping away at our enormous mortgage while market appreciation did its work.

What this meant for us was that instead of spending the $2,000+/month that families our size spend to rent, my parents’ financial assistance was allowing us to actually build equity by paying down a mortgage instead. And in that sense, it put us on a completely different financial trajectory.

My Parents Made the Difference

What strikes me about my story is that my wife and I aren’t special. Both of us earn modest five-figure incomes, which puts us in the same company as most couples our age.

What separates our story from that of many couples is that 2006 gift from my parents. Again, we aren’t talking Donald Trump money here — we’re talking low five figures. But that act of assistance was an absolute game-changer in my life.

I’ll be grateful for it for as long as I live.

The Down Payment Savings Struggle is Real

Today, the reality for most middle-class millennials is that putting aside enough money for even a 5–10% down payment (plus associated purchasing costs) in today’s market is a daunting challenge. Even at a steady rate of $1,000/month or $12,000/year in savings, these couples are looking at consecutive years of disciplined saving in order to put even a small down payment together.

And let’s face it — with high rental prices, student loans, car payments, rising gas and grocery costs, the costs of raising children, etc. — most millennials and gen-x couples aren’t banking $1,000 month over month. Even with no-fluff, scorched earth budgets, those savings aren’t easy. To make matters worse, market prices are unpredictable and prone to sudden increases.

Some Parents May Not Realize Their Ability to Help

One person’s housing crisis is another person’s equity windfall. In markets that have experienced rapid appreciation, long-time homeowners enjoy the benefits.

Of course the tricky thing about market appreciation is that it doesn’t affect cash flow whatsoever. A $1M gain in property value doesn’t translate into any more money for groceries.

And it’s for that reason that I think many parents — and to be clear, I’m not thinking of my own parents or my in-laws here — simply don’t realize the incredible power to help that they hold.

They don’t feel rich. And in a practical, everyday kind of sense, they may not be.

But thanks to the equity in their properties, they have tremendous power to be game-changers.

The Power of a HELOC

HELOCs, or home equity lines of credit, mean that baby boomers can borrow large sums at low interest by using their own home as security.

Let’s take a fictional Bob, his wife Shirley, and their daughter Jenny as examples.

Bob and Shirley purchased a home in 1990 for $300,000. In the years since, they raised a daughter that they love very much. As little Jenny grew from toddler into young professional, Bob and Shirley used their modest incomes to pay their mortgage faithfully. Today, their mortgage principal is at $50,000.

Their home has appreciated well over the last decade. Though the numbers don’t make any sense to Bob and Shirley, the local tax assessment assigns their home a market value of $1.1M.

Bob and Shirley are sitting on over $1M in equity, but they definitely don’t feel very rich. As prices rise, they continue to spend frugally throughout the year in order to maintain a modest lifestyle and remain on a track of responsible savings and investment for retirement. These are wise and responsible goals.

What Bob and Shirley fail to see is the power of a home equity line of credit. They miss the fact that a bank would gladly lend them $30,000 at 4%, or just $1,200 in interest per year.

For just $100/month, they could give or lend $30,000 to their daughter, Jenny. And that $30k would be enough for Jenny to purchase a condo.

Not a grand place. But a toe in the market. A place to call her own.

Heck, Jenny could even pay the interest on her parents’ HELOC herself, meaning the loan wouldn’t cost Bob and Shirley anything at all. By the time she sells her first property to upgrade to her second, Jenny should net enough from the sale to pay her parents back in full.

Think about that for a second, because this is the point I’m trying hard to make.

For no cost at all, these parents could completely change the financial trajectory of their daughter’s life.

Don’t Hear Entitlement

This piece is a bold argument to make, and some will hear millennial or gen-x entitlement here (I fall into either generation category, depending on the source you go by).

Please don’t hear entitlement. I fully recognize that not every parent is in a position to do what my parents did for me. In my case, I’ll be forever and humbly grateful.

Far be it from me to tell any other person — of any age or status — how to manage their hard-earned money.

Instead, I write this piece out of a place of genuine care. Out of a genuine belief that there are families who could be multiplying their wealth generationally, but don’t understand how to do it.

I write out of the knowledge that there are professional couples out there whose parents are sitting on the means to absolutely transform the financial futures of their children at little to no cost at all. They just don’t realize it.

A Legacy Move

Of course the best part about my parents’ financial help is that one day, my wife and I will be able to help our boys out in the very same way. That makes me smile.

The help may not be a lot. And like the Jenny scenario I described above, it may be a loan instead of an outright gift.

But it will be enough to help them get into the market, something that will help not only them but their families as well.

The gift that my parents gave back in 2006 will continue to give for years and even decades to come. And that’s a powerful thought.

It makes their gift a legacy move. One that changed a family tree for generations to come.

When it comes to today’s real estate, baby boomers can be game-changers.

Categories
Family Legacy Tribute

Celebrating my Dad

A few months ago, I was honoured to share a short tribute at my father’s retirement celebration from Faith Academy, an independent K-12 school in Winnipeg where he had served as principal and director for 25 years. I’m posting my words from the video tribute below, partly to honour his legacy and preserve part of his story for future generations of Caveys.

As I think about my Dad’s career at Faith Academy, a few highlights stand out. As a Grade 8 student back in the days when our Jefferson campus housed the entire school, I remember well the strange new experience of seeing Dad walk the halls as principal. Although he was new to education, Dad projected the sort of strong leadership that the school needed and my peers respected.

Later, in my university years, I remember working at the Stonewall campus of Faith Academy. Of course I was known there as Mr. Cavey, and so on the days when Dad visited the school, he was referred to by some of the kids as “Mr. Cavey’s dad.” A few years later, I was thrilled to accept my first Faith Academy teaching contract. Although it wasn’t my dad that interviewed me, he was very clear that he was proud of the track my own career was taking at that time.

My dad’s legacy at Faith Academy makes me very proud. When I think of his years of service, the words that come to mind are faithfulness, integrity, and compassion. I know Dad’s serious demeanour could intimidate some, but those that were privileged to work with him for any length of time would observe how kind and caring he was. Dad’s also been a very principled leader, keeping the school on solid financial footing and making the sorts of decisions that protect the school community. Most importantly, I think Dad has helped cast a vision for Faith Academy’s unique mission and calling in Winnipeg.

Dad, you continue to inspire me personally and professionally. Congratulations on a well-deserved retirement.