Redefining Success
It was 1985, and I was an out-of-work certified public accountant (CPA) who had recently been laid off by a global accounting firm in Seattle after only two years on the job. With my pride bruised, and feeling like a failure, I decided to sign up for the stockbroker trainee program with Dean Witter Reynolds & Co. Several friends were making a good living as brokers, and the stock market was starting to reach new highs. The stockbroker role seemed like a better fit for my relationship skills and abilities than being an accountant, and I really wanted a job where I could help people.
Over five grit-tested years, I built a brokerage clientele through what was referred to as “smiling and dialing,” the popular method for reaching prospects during that decade. My goal each day was to cold-call a minimum of 40–60 residences or businesses in my local area with an investment idea and open new accounts that would lead to future investment sales and commissions. After the 12-month training period ended, my pay was 100 percent commissions-based, and that was all the incentive I needed to learn quickly how to become proficient at selling stocks, bonds, and mutual funds to anyone who would listen to me.
The grind of commission sales became more and more of a challenge partly because of my original CPA training as a trusted resource, and also my desire to be viewed by clients as something other than just a salesman. Fortunately, as my tolerance for cold-calling was running low, I was approached by my wife’s uncle, who was working for a wealthy family in San Diego that recently experienced a major liquidity event from an initial public offering (IPO). They were setting up a family office in Bellevue, Washington, and needed to fill a chief financial officer (CFO) role. Their ideal candidate needed experience in the financial markets and would work directly with the family patriarch and chief executive officer (CEO). I jumped at the chance to shift my career focus closer to what I believed was calling me forward in my personal evolution.
The traditional family office was the genesis of the wealth management industry we have today. For many years, multigenerational wealthy families created central financial hubs where all financial matters for the family were handled, including investing, accounting, property management, estate planning, and legal, insurance, and other financial and concierge-type functions, such as travel. The goal of this unified approach is to protect and maintain the privacy of family assets through professional management, coordinated results, improved efficiency and costs, and streamlined communications through the family office.
My CFO role in this family office exposed me to a world I had never experienced before: family assets of over $100 million (in 1990), commercial real estate development and leasing activities; a significant stock portfolio; several operating companies; extravagant personal residences, cars, and airplanes; a world-class investment and legal team; and about ten office employees. I was starting to understand what it felt like to have a seat at the table as a trusted advisor, with access to comprehensive and confidential details about finances and family objectives, as well as the ability to influence decisions.
It didn’t take me long to become curious about who else performed this type of holistic and conflict-free advisory service to wealth creators. Microsoft was just starting to mint new millionaires, and I was confident that there would be a demand for the comprehensive wealth management services I experienced in the family office setting. This next generation of wealth creators wanted an approach that would provide most of the benefits of a full-blown family office, with much lower cost and hassle factors.
I saw a clear vision of where the financial advisor business was heading, and my quest to engage in this line of work led me to a very unique company doing multiclient advisory work based in Silicon Valley. They understood the needs of these new wealth creators and were building a platform to serve them. They recognized the growing technology field and the new wealth being created in the Pacific Northwest, and I opened their first satellite office in Seattle.
It seemed like I had it all: I had obtained advanced designations (CPA and CFA) and an engaging career, and I was happily married, with three young kids attending excellent private schools, a new house in the suburbs, and a dog. I regularly attended church and participated in several nonprofit activities, and I was making more money than ever before, working with clients at cool technology companies. I was checking all the “success” boxes in terms of life and money.
However, under the surface, something wasn’t right. I was experiencing anxiety symptoms that were becoming more and more frequent and pronounced. At one meeting with a major estate-planning group in Seattle, I was visibly sweating and uncomfortable and had a difficult time speaking. I was also increasingly at odds with the direction of the company I worked for and the life philosophy of the owners. It can be difficult to be in the satellite office of a firm: You are outside the culture and don’t rub shoulders day to day with key players, including your bosses. The upside was I had tremendous freedom to build client relationships and set up the office the way I wanted to.
The owners wanted to see my satellite office grow even faster, and they decided to expand the leadership team beyond me to protect client relationships should I decide to leave. Several new employees were added to the office, including the nephew of one of the owners. We were intentionally put into direct competition with each other; there was friction about prospects and referral sources, and virtually no trust. From my perspective, the owners were focused on getting rich at all costs, prioritizing work and status over relationships and suggesting that life balance was for the weak. Money, and lots of it, was their sole aim, regardless of consequences. I was just beginning to understand that my own purpose and career objectives were grounded at a much deeper level.
In January 1999, I made a routine trip to Menlo Park, California, to the company headquarters. The office was on Sand Hill Road, a prestigious address in the epicenter of new-tech money south of San Francisco. The event was my annual performance review, given by the two owners of the firm. I was performing well enough on paper, but my body was telling a different story.
Perry, one of the owners, suggested to me during my review that I was duplicitous. (At the time, I didn’t know what that word meant and had to go look it up.) Perry recognized an incongruence between the “Everything is great” story I was telling and the underlying emotions I was experiencing and not sharing. The world of success and big money had collided with my life view, and they weren’t in harmony.
Perry’s comment really shook me because I lived by the virtue of honesty, and in that moment, I realized I wasn’t being honest with the owners or myself. I wasn’t intentionally being deceptive, but there was an internal wrestling match going on around my lack of happiness and fulfillment and my evolving definition of success. Perry gave me a gift that day by telling me the truth of what he saw.
By all outward measures, I had achieved “success” at this point in my life. But I wasn’t happy, healthy, or at peace. Unfortunately, this is true for many “successful” wealth creators. I worked with a fortysomething venture capitalist named Rob who had achieved a substantial amount of wealth early in his career. He admitted that creating the wealth took a big toll on his life—it required maniacal focus and all his energy, resulted in broken relationships, and required him to put his own wellness on the back burner.
I asked him: Would he change anything if he could go back in time? His response seemed contrary to common sense: He said he would likely do it the same way again because he wanted to have the financial resources to choose his life, send his kids to private school, and enjoy other lifestyle comforts. I share this story because I believe it represents a formula that many of us follow simply because it’s the only one we know. Work ridiculously hard, create success in the form of wealth and power, and sacrifice our health and relationships along the way, in the hope of someday figuring out the life we really want, when we have time to think about it.
In an interview, best-selling author and vulnerability expert Brené Brown advised: “Defining success is one of the most powerful things you can do as a family, as a couple, individually. There is a default definition [of success] that is, ‘money, materialism, accomplishment, and achievement.’ ” Brown explains that burnout and damage to our physical and mental health are often the result when we narrowly focus on achieving traditional measures of success (namely, money and power).9
Obviously, money is a powerful motivator, and as my client Rob expressed, he was willing to sacrifice his time, energy, health, and relationships for the comforts, choices, and “freedom” that money provided. It seems a very normal path for many to empire-build earlier in life. In my own life, I’ve seen evidence of this pattern, especially in my 30s. Our culture promotes the idea of success being defined by material possessions: houses, cars, “stuff”—everything money can buy. All this stuff is supposed to make us happy. A 2010 study from Princeton University demonstrates that once someone achieves an annual salary of $75,000, they don’t report any greater degree of day-to-day happiness, no matter how much their income increases.10 Once our basic needs are met, the utility of money as a component of satisfaction starts to level off.
There is another, deeper reason Rob stayed focused on financial outcomes exclusively: because it keeps us distracted from having to author our life—something we aren’t taught how to do. If we stay distracted with empire building and financial security, we don’t have to dig into the uncertain world of knowing ourselves and defining and designing a future. It’s just easier to try to win on our financial scorecard. And to be fair, the busyness of demanding professions combined with raising a family and keeping up with many responsibilities leave many wealth creators with little time to consider the impacts and outcomes of success and money in their lives.
A Richer Definition of Success
There is nothing wrong with wanting it all. I wanted more for my life back in 1999, when I realized I couldn’t continue on my current path. I wanted to flourish in every facet of my life—financial, career satisfaction, family, health, and other personal goals that mattered to me—and I wanted adventure to go along with it. I only had one life to live, and I wanted more passion and purpose. I wanted to know myself better and heal from the anxiety that plagued me. I wanted to go on a spiritual journey that required putting my faith into action. I wanted to understand what I was made of, what made me tick, and what was possible.
I wanted the time to coach my son’s baseball team and to be an active and available parent for our kids. I wanted to spend more quality time with my wife. I wanted to put my stamp on the world by creating and innovating a business culture that valued caring for people, pursuing excellence, personal growth and development, and life fully lived. I also wanted to build wealth, experience financial success and security, and be generous.
Starting a company was a long shot when I was younger, but at age 37, I felt this was my last chance to create the future I desperately wanted. There was a lot at stake: We had become financially comfortable with my salary and its accompanying lifestyle perks. We had ratcheted up our spending commensurate with my raises, and I definitely didn’t want my lifestyle to backslide. Regardless, it was clear to me that in a few short years I’d be 50, and I didn’t want to be financially comfortable, unhappy, full of regrets, and stuck.
During the next three months, I began preparing to launch my own business—I secured a small executive office space, bought a computer, picked a company name, made a list of projects and priorities, and prayed a lot. There were many long talks with my wife, Kelle, about what I planned to do. She was my life partner and the co-creator of our wealth, and I knew I wouldn’t be able to move forward without her support, trust, and commitment. We needed to be in complete alignment.
On May 5, 1999, the night before the planned launch date, I was full of fear and anxiety because of what I was about to risk. I remember feeling like I was at the top of a very large cliff, looking down at the water below. I was literally scared to death, unable to sleep; the pressure in my chest was overwhelming, not sure if the water below was safe.
The next morning, I jumped. The water was fine, and Highland was born.
In the nineteen years since then, I’ve lived my way to a richer definition of success. I realized that I didn’t want financial success at the cost of missing all the other sweetness of life during the journey. Some components of redefining success for myself included:
I believe we will end up with a better life outcome if we take a more holistic and thoughtful approach to defining success, moving beyond purely financial objectives. You can’t take the money with you when you die, and as many studies have shown, it doesn’t increase happiness.
In a 2018 interview, the comedian and actor Jim Carrey talked about “getting to the place where you have everything everybody has ever desired and realizing you are still unhappy.”11. Journalist and author Kirsten Powers points out in an article in USA Today that we live in a culture of disconnection from family, friends, and our communities, while relentlessly pursuing the outward trappings of success: a promotion, a raise, a new car or house. She writes: “We are too busy trying to ‘make it’ without realizing that once we reach that goal, it won’t be enough.… In many ways achieving all your goals provides the opposite of fulfillment: It lays bare the truth that there is nothing you can purchase, possess, or achieve that will make you feel fulfilled over the long term.”12.
What if our definition of success shifted to “significance” instead? What choices would we make if we believed that our lives matter much more than our pocketbooks—that success is measured by the kind of person you become, the quality and depth of your relationships, the empathy you show, the generosity you share with those in need?
The millennial generation is embracing a new way to look at life that is broader and more robust. They are breaking down the idea that money is the end-all, and the only objective measure of success. They don’t want to waste their prime years focused exclusively on empire building. They want to taste the fruit along the way, not just near the end of the journey when success is assured. While the American Dream is built on acquiring material goods, millennials would rather collect experiences than things.
According to a survey conducted by Harris and sponsored by the Web platform Eventbrite, “[T]his generation not only highly values experiences, but they are increasingly spending time and money on them: from concerts and social events to athletic pursuits, to cultural experiences and events of all kinds. For this group, happiness isn’t as focused on possessions or career status. Living a meaningful, happy life is about creating, sharing, and capturing memories earned through experiences that span the spectrum of life’s opportunities.”13.
Millennials also expect more from their jobs. According to the 2015 Deloitte Millennial Survey, which researched more than 7,700 millennials spanning 29 countries, 6 out of 10 respondents said that “a sense of purpose” is why they chose to work for their current employer.14. Millennials also aren’t chasing jobs for higher salaries—they are looking for companies that share their personal values. According to the same survey, 7 out of 10 believe that the company they work for shares the same personal values as them.
The joy really is in the journey. This is why experiences enrich our lives more than stuff. Alice, a Fortune 100 executive, found “significance” in designing life experiences for her family. Recently, she took her son to Japan on a mother-son spring break adventure. Although she could afford to book five-star hotels and travel first class, Alice specifically chose coach airline tickets and staying at an Airbnb.
She wants her kids to stay grounded, experience what scarcity looks like, and understand that you can have great experiences without spending a lot of money. Her goal was to build a wealth of family experiences that would be remembered and valued. Isn’t it interesting that what we really treasure is our memories with people we love and care for? Those satisfy, whereas more stuff is just an endless game of “bigger and better” that never really ends.
Maximizing Your Life
Redefining what success looks like for you is the first step toward maximizing your return on life. When money is the only metric we measure, we can easily become obsessed with hitting a certain financial target rather than finding satisfaction in our relationships, experiences, and other goals. Each of us needs to find our level of financial “enoughness.”
This can be challenging for driven wealth creators, who often live in the financially skewed bubbles of high-income, high-growth communities, such as Silicon Valley, New York City, Seattle, and elsewhere. It’s easy to feel relatively middle class in places where there is always someone with greater assets, a bigger house, a nicer car, and even an airplane, where everything is expensive (especially real estate and education) and neighbors are enjoying an everyday lavish lifestyle. You quickly become used to a certain level of spending, and lifestyle creep is difficult to control. “Enough” is never quite enough when we compare our wealth to those with more than us. If you never put a boundary around your needs, the line keeps moving, and financial security will always be just beyond your reach.
Christopher, the CEO of a successful start-up in Seattle, shared with me that his goal was to reach $10 million of liquid assets, in addition to his valuable home and vacation properties. He told me this was his “F-you money.” I asked him to define what he meant by that and why it was so important to him. He told me this was the “minimum” amount of money where he could literally do whatever he wanted and didn’t have to play “the game” anymore. By hitting this number in his bank account, he felt he would be immune from needing a job or to rely on anyone else.
This extreme desire to separate ourselves and be self-sufficient is unhealthy and creates unnatural hoarding and accumulation drives. The need for financial security is grounded in our desire to control the uncertainty of the world around us. But we falsely believe that if we have a large-enough asset base, we can mute our volatile emotions and find peace in the “safety” of amassing the biggest pile.
I encourage you to sit down and calculate what financial “enoughness” looks like for you. Either through a wealth advisor or using any number of free online tools and resources (see the Appendix for more details), you can create a financial plan that evaluates the sustainability of your current rate of expenses, relative to your income and savings, in order to determine the probability of having enough to meet your planned needs. Estimates on certain expenses and expectations are important to try to pin down, such as inflation, taxes, and investment returns, because they play an outsized role in the results. Also, keep in mind that certain expenses are affected by inflation more than others, such as college tuition and medical costs.
It’s best to consider this exercise as part reality and part envisioning your desired future—a way to gain a more realistic picture of the asset base you will need to fund your hopes and dreams. The beauty of most financial planning software tools is that you can make adjustments based on various assumptions, changing the variables to immediately see how differences in income and expenses affect the end result. This exercise is a useful tool in strategically designing your financial life to include your needs, wants, and wishes. Seeing actual numbers helps build confidence and clarity.
Of course, life can change quickly, and so can financial assumptions, but by revisiting these calculations at least annually, you can review your commitment to your outcomes and see what adjustments need to be made. It can also be an opportunity to draw a circle around your lifestyle spending and look for opportunities to improve your stewardship of the resources you have, preserving the excess, and building a “more than enough” pot for contributions to people and causes you care about.
When we step back and take a good hard look, the level of abundance of any wealth creator when compared to the rest of the world is staggering, where the top 1 percent income level globally is about $45,000. That puts wealth creators, and much of the middle class, in the stratosphere of wealth compared to their global brethren, with no need to worry about obtaining basic necessities and plenty of opportunity to acquire anything on their list of desires.
Ironically, studies on generosity conducted by Christian Smith and Hilary Davidson at Notre Dame University demonstrate that by clinging to what we have and protecting ourselves against future uncertainties and misfortunes, we become more anxious and are actually more vulnerable to future misfortunes. Generosity is the secret joy creator. When we focus on making a significant difference in the lives of others, we enhance our own well-being. Smith and Davidson’s research shows a consistent link between demonstrating generosity and leading a better life: Generous people are happier, suffer fewer illnesses and injuries, live with a greater sense of purpose, and experience less depression.15.
One of the benefits of calculating your level of financial independence is gaining clarity about your gifting capacity—the resources you have over and above your needs, which you could give away, now or in the future. (We will review gifting capacity and philanthropy more in depth in Chapter Three.) I believe that many people aren’t more generous because they really don’t know what they can afford to give, so they sit on their hands.
Knowing that you can give, and how much, is empowering. This is the quantitative aspect of giving: crunching the numbers to determine your financial ability to give. The next element is qualitative in nature, derived from your personal definition of generosity. Kelle and I approach generosity from a faith perspective that suggests contributing 10 percent of our income to church and other charities. We haven’t always reached that level of giving in the past, but our commitments are leading us in that direction.
The final element is experiential, where your heart is drawn to give through personal experience. This is where aspiring wealth creators can experiment with giving, even small amounts like $50 or $100 to charities that interest them, and begin creating an emotional connection to one or more charities or causes. The amount of money is secondary to connecting your heart to what ultimately drives a very personal decision about how much to give.
Once you have a clear picture of how much money you need to achieve your life vision, you can determine how to define “enoughness” for yourself. Additional wealth becomes surplus, and this is where the heavy lifting starts. This is where we can begin figuring out for ourselves what that money is for. Because I only have one life to live, I want my life to be the best it possibly can be, and not just financially. Life, just like wealth, is a gift, and we all desire a meaningful return on investment. What a shame it would be to live a small, minimized, underproductive, and ineffective life. When I look back, I want to have maximized my life and to have lived it to the fullest.
I want all wealth creators to experience the richness of life I’ve been blessed to enjoy through discovering a new definition of success. In refocusing my life on relating, creating, learning, and giving, I’ve found this to be true: Success is about so much more than money.
In the next chapters, we’ll explore the practical realities and emotional undercurrents for wealth creators as they journey through the Wealth Life Cycle and learn to manage the complexity that comes with increasing wealth.
QUESTIONS TO CONSIDER AS YOU EXPLORE YOUR OWN RELATIONSHIP WITH MONEY AND SUCCESS: