Does money buy happiness? What I learned about success from starting my own business

It’s time to rebrand the concept of success as something holistic, heartfelt, and purposeful. By doing so, you can experience radical levels of happiness.

Looking back on my career, I’ve come to realize how much my definition of success has changed over time. My years spent advising some of the most successful wealth creators in America have taught me that money comes with unexpected challenges and great wealth does not equal great success.

I started my career as a CPA, and eventually, I was hired as the Chief Financial Officer for a wealthy family that was setting up a family office. A “family office” is where all financial matters for a highly affluent family are handled including investing, accounting, property management, estate planning and legal, insurance, and other functions. My CFO role in this family office exposed me to a world I had never experienced: significant family assets including commercial real estate development and leasing activities, a large stock and bond portfolio, several operating companies, extravagant personal residences, cars, and airplanes, and about 10 office employees.


Follow Ladders on Flipboard!

Follow Ladders’ magazines on Flipboard covering Happiness, Productivity, Job Satisfaction, Neuroscience, and more!


The tech boom was minting new millionaires at a fantastic rate, and I recognized a growing need for holistic and conflict-free wealth advisory services. I was hired to open an office in Seattle to provide such services by a Silicon Valley firm.

Soon I came to a crossroads in my career: I had achieved “success” at this point in my life, but I wasn’t happy, healthy, or at peace. I was at odds with the philosophy of my bosses, who were focused on prioritizing work and status over relationships, suggesting that life balance was for the weak. I was just beginning to understand that my own purpose and career objectives were grounded at a much deeper level.

After seven years at the firm, I prepared to launch my own business. The night before my planned launch date, I was full of fear and anxiety because of what I was about to risk. The next morning, I took a leap into the unknown and Highland was born.

Over the past 20 years, I’ve lived my way to a richer definition of success. It wasn’t a straight line, and I made tons of mistakes along the way. However, these three lessons have been incredibly valuable in my quest to redefine success for myself:

You don’t need to sacrifice your health, your relationships and other important objectives to build wealth.

When I started Highland, I had this crazy idea that I wasn’t willing to sacrifice anything – I wanted it all! I recognized that I only had one life to live, and I wasn’t going to listen to naysayers who might question my choices. I knew that I was biting off a lot by starting my own business, but I wasn’t willing to postpone my other life objectives until the business was successful.

I was being called into a much broader definition of success that included priorities like coaching my 13-year-old son’s select baseball team. I didn’t want to just show up and help once in a while. I wanted to be the head coach, responsible for practice plans and motivating the boys to develop and learn important life skills.

The tradeoff was that my business grew at a slower pace, and I was okay with that. I was willing to exchange what I viewed as excess revenue growth for the priceless memories I made on the baseball diamond with my son. This experience, along with others, taught me that I could push seemingly rigidly defined boundaries in my mind about what was possible. I didn’t have to settle for anything less than what I believed mattered most.

Strive for continuous learning and growth

There is a saying that a business will only grow as fast as its leader. I knew I had to be the one leading the charge, evolving in my role, my capabilities, and my contribution as a businessman and a human being. Other people in my company were watching and taking their cues from me.

I quickly realized that when you start a business, all of your deficiencies and flaws are exposed: as the boss, you don’t have anyone else to blame or hide behind. I had to get better at leading people, building strategy and vision, effectively communicating my needs, and holding people accountable even if that meant conflict.

I found the courage to seek counselors, coaches, and mentors who listened, gave me advice, and helped me become a better version of myself. Highland was a canvas where God could shape me into who I needed to become. I now recognize that continual growth and development are critical to thriving, personally and professionally.

Generosity is the secret joy creator

I truly believe in the saying: “You’ve never met an unhappy generous person.”

It took me a while to fully understand the power of pure contribution – those moments where I’m not trying to gain anything in return from providing value to someone else. When I bring my full potential and gifts to every business and personal interaction, without any expectation of a return, I feel intensely alive, full of energy and joyful. I like to focus on being generous with L.I.F.E. – Labor, Influence, Financial, Expertise.

Generosity isn’t just about giving financially; it’s about looking at all the interactions in my life as an opportunity to bring the presence of loving-wisdom as a gift. This philosophy helped me approach interactions with my employees differently. Instead of fearing what might happen in the future if they left the company, I shifted my focus and started asking, “Where are you trying to go?” and “How could I help you get there?” Generosity creates freedom as we view our life through an abundance mindset, and there are great payoffs for the giver as well as the recipient.

It’s time to rebrand the concept of success as something holistic, heartfelt, and purposeful. By doing so, you can experience radical levels of joy from your money, work, and life. Don’t be deterred from redefining success for yourself.

John Christianson is founder and CEO of Highland Private Wealth Management, a boutique financial life management company in Bellevue, Washington. For more than 25 years, John has managed the financial lives of some of the most successful wealth creators in the country, including executives at Amazon, Microsoft, Starbucks, Nike, and Facebook and has acquired unique insights into the challenges and opportunities for wealth creators. John is a CFA charterholder, a CPA-Inactive, and a certified professional coach with the International Coach Federation. He is also the host and creator of The Wealth Confidant Podcast.


You might also enjoy…