Leadership

Play it safe or bet on yourself

Headshot of Jasper Smith
Jasper SmithAugust 27, 2024
A person sitting by a window is depicted massaging the bridge of their nose, a gesture of stress or deep thought, surrounded by a serene indoor environment.

I will never forget the day that email hit my inbox. The message alerted me that the rotational program I was a part of was going through some major changes. It was 2008 (the Great Recession), and I was working at a financial services firm in the San Francisco Bay Area.

The email offered two options:

  1. Accept one of the limited number of open positions in the down-sized program. The experience would mirror my first-year, and I’d have to move back to Philadelphia.
  2. Take a severance package at the conclusion of my rotation.

I had some tough decisions to make.

Facing tough decisions

I was 22, a long way from home, and loving my independence. But I was clueless about my next professional move and that uncertainty was scary.

I didn’t like option one. I couldn’t see myself moving back to Philadelphia to work another year doing something I’d already done. Philadelphia is a cool place, but I was having an incredible experience living in California, and I needed more time in the Bay Area.

Between the pragmatic side (stalling for a year doing redundant work) and the more idealized side (exploring a new place), it was clear option two was the way to go.

So what was my next move? I’d only been out of college a year and a half. I was enjoying my time working in a support role in a financial planning office, but the thought of going out on my own and becoming a full-time financial planner was intriguing.

I had some transferable skills and multiple securities licenses. But I was uncertain about going out on my own because I had never sold financial products, and I had no experience running a financial planning business.

So I scheduled appointments with two of my managers.

Two perspectives for 22 year old me

FIRST MANAGER’S ADVICE

“You’re 22 years old. You don’t have any kids and no real responsibilities. Why not give it a try and see if you can make it work. This career path is challenging when you first start but it can be extremely rewarding over the long-term. Plus, what’s the worst that could happen, you fail? So what if you fail. Nobody is going to care. They might even respect that you tried something that people are afraid to do–bet on themselves.

If failure ends up being the result of your financial planning business, you won’t have any problems getting a job. You possess the right securities licenses that will make you a top candidate at any financial services company. If I were you, I would take the leap and see what happens. You don’t want to be that old guy looking back on your life and having to say to yourself ‘what if I had given it a shot?’”

SECOND MANAGER’S ADVICE

“You’re 22 years old. You don’t have any kids and no real responsibilities. But, you’re young, and people don’t typically buy financial products from young people. You’ve only lived in the Bay Area for a short time, so you haven’t had enough time to build a network of people who will be willing to do business with you. If I were you, I’d take a salaried job with another financial firm, build my network, beef up my cash reserves, and slowly plot out my plan of running a financial planning business in a few years.”

My dad’s simple, yet powerful advice

Next on my list was my dad. He was an entrepreneur but in a completely different industry. I knew he would help me make this critical decision about my next move. I called him and shared what both managers told me. He liked the advice both had given me. He liked the advice both had given, and in less than five minutes, he broke things down for me.

Dad: Jasper, you took a chance and fought hard to get that position in California, which is what you wanted. You did everything in your power to make that a reality. Now, the economy isn’t doing you any favors, but you can’t control the economy.

You can only control the decisions you make. You are now faced with a decision that has an expiration date. You went to college and graduated, so I know you’ll be able to figure this out. There are no right or wrong decisions about the career path you take. They’re just decisions, and you must be able to live with the decisions you make. I’ll support you no matter what you decide but ultimately, the decision is yours and only yours to make. So, what do you want to do?

Me: I don’t know, which is why I’m calling you.

Dad: Well, when you figure out what you want to do, let me know.

Then, he hung up on me.

I stared at the phone for a few minutes, feeling anxious and afraid. I soon realized my dad was challenging me to grow up and make a decision. I decided to take the leap into the financial planning business. The moment I made that choice, my fear subsided.

Working, but staying true to my vision

Fast forward 16 years later, I’m still working in the financial services industry as an entrepreneur. My journey hasn’t been easy, and I’ve had to get extremely comfortable with failure. I struggled to find good mentors early on. I’ve dealt with racism and a lack of support from “leaders” in the industry. I even quit a few times and took jobs in the non-profit sector.

But I keep returning to entrepreneurship. I can't fathom what my life would be like if I chose the “safe” corporate warrior route.

The #BuildWealth Movement®, like all businesses, started out as an idea. Then it morphed into a social media campaign. Then it became a full fledged business. I’ve made tens of thousands of investments into the business, some which were incredible for growth, while others I have had to accept as learning experiences. The growth I've experienced on my entrepreneurial journey has been invaluable.

Plus, I still have a recurring nightmare about what would happen if I left the entrepreneurial world to take a secure job with a company.

I’m worried that the day I decide to go the safe route, I’ll get a call or email from a major client eager to work with me, or an opportunity that could lead to a nine-figure success. I wouldn’t be able to live with myself if I had to say, “Unfortunately I’m no longer in business, and I’ll need to refer you elsewhere.”

This is why I keep going.

If I left my business behind I might miss out on a life changing opportunity or client. If I worked a steady job, I could earn a decent income, but staying hungry as an entrepreneur gives me unlimited earning potential.

Twenty-two year-old wanted to become a financial expert who would transform millions of lives. I wanted to become a household name. But it’s never been about fame. I want a lasting form of recognition, to be respected for my expertise, insights, and the enduring impact I make as a thought leader in the financial services industry.

I’ve witnessed many financial influencers come onto the scene and then vanish within a few years. That’s not how I operate. I’ve been at this for almost two decades, and there’s more impactful work to do.

I also had some indirect encouragement in the form of people who said they would wait until retirement to pursue a career, start a nonprofit or launch a business they were passionate about.

That never sat well with me.

Essentially, you’ve spent your entire life working a job that didn’t fulfill you. Yes, it helped you pay the bills, but is that all life is about? Pay your bills, go on vacation and then finally pursue your passion once you hit your late 50s or early 60s.

That can be a really fulfilling (and necessary) choice for some people.

But spending 30 or 40 years dreaming about my business scared me. I needed to wake up every day and stay on my entrepreneurial journey because it makes me feel alive.

Today, my vision remains clear: I want to change the way people think and feel about money and work to help them disrupt generational poverty® for their family and community.

I have zero regrets about the path I chose at 22. I don’t waste time wondering how my life might have been different if I hadn’t taken that leap. I’m grateful for every part of my journey, and every day I wake up excited to face new challenges and welcome greater success.

If I’m lucky enough to grow old, I’ll be able to look in the mirror and say, “You never hesitated to chase your dreams.” And I’ll smile.

I think about that day often, and despite the daily challenges, I feel alive. I’m truly living, and it feels amazing. I doubt many people who stay on the corporate path their entire career can say that. We all have a path to choose, and I’m glad I chose mine.

I’ll wrap this one up with something I’ve heard many successful people say. It’s something I carry with me daily: I would rather be a failed entrepreneur than someone who never tried.

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Headshot of Jasper Smith
Jasper Smith

Jasper Smith has been involved in the financial services arena for over fifteen years. He currently works as a Financial Planner with Prudential and he’s the chief visionary behind a financial education company called The #BuildWealth Movement®. He works tirelessly to help people disrupt generational poverty® for their family and community.