Why Most People Fail | They're Listening to the Wrong Voices

Tommy Nickerson walked into his first financial services interview with a ponytail, colorful language, and stories the interviewer did not find funny. The guy walked him out with a hand on his shoulder saying, "You'll figure it out. Just not here."

Two weeks later, Tommy stood up in front of his new team at Florida Financial Advisors and said five words that pissed everyone off: "I'm gonna be your boss one day."

Seven years later, he is. Today Tommy serves as Senior Vice President at FFA, supporting over 350 advisors across markets from Florida to Rhode Island to Texas to Denver. He has developed more leaders within the company than anyone else. The Jacksonville office he built from scratch became the most productive in the organization, beating Tampa in just three years.

"When people give up on their pursuit of what they want for themselves, it's actually a form of arrogance. They lack humility. They're not understanding how lucky they are."

Tommy did not start with a plan. He graduated from Bentley University with a finance degree he never intended to use. He Google searched "most consecutive days of sunlight in the country," packed his bags, and flew to St. Petersburg, Florida the day after graduation. He worked as a saute cook while studying for his licensing exams, splitting a bedroom with his best friend and leaving work at 4pm to prep dinner service until midnight.

In this episode of the Take The Power Back podcast, Tommy sits down with Jason Mickool to break down exactly why most people fail and what separates those who make it from those who flame out. The conversation covers the three things every leader needs, why you should never take advice from people who care about your feelings, and the mindset shift that turned a long-haired hippie into an executive.

Watch the full conversation on YouTube or listen on Podbean.

Table of Contents

The Three Things Every Leader Needs

Tommy boils leadership down to three questions. Do your people trust you? Are they loyal to you? Do they respect you? If you cannot answer yes to all three, that is exactly where you need to focus.

"If I could boil down leadership, there's three things. Do you have trust with your people? Do you have loyalty from your people? And do your people respect you? If you can't say for sure, then just go work on those three things."

Trust takes time and is easy to lose. You build it by doing things in other people's best interest, even at the fault of your own. Loyalty is behavioral. If you want it from others, you have to demonstrate it first. Respect comes from getting in the mud with your team. Tommy hates being behind a closed door. To a fault, maybe. But that is how you earn it.

He uses a freeze game with young leaders he is developing. Stop and ask yourself: is what I am doing right now gaining trust, gaining loyalty, gaining respect? Or am I losing it? That moment of self-awareness catches people and helps them get others on board.

Leadership dies when you start defending your position instead of serving your team. The more you hold on, the faster people smell it. And people are smart. They are always watching.

Why You Should Stop Taking Advice From People Who Love You

Tommy's mom once asked him if he was sure he should stay in financial services. He was working long hours and struggling early on. She suggested he could go to Fidelity and make $50,000. His dad met a guy at a bar who said only one in ten advisors make it.

Both of his parents are unbelievably supportive. Both gave terrible advice in that moment. Why? They had a vested interest in his feelings, not his success.

"Seek feedback from people who have a vested interest in your success more than a vested interest in your feelings. The people who love you the most often give you the worst advice because they give advice based on feelings."

Tommy's best friend Brendan never coddled him. When Tommy's parents got divorced and everyone else asked if he was okay, Brendan laughed and said "What's the big deal? You get two Christmases." When Tommy practiced his pitch at home, Brendan would look at his whiteboard and say "That sucked." To this day, Brendan challenges his assumptions.

If you want to be the best basketball player in the world, you do not ask a painter for advice. You find someone who looks like where you want to go and do exactly what they tell you. Most people never take a step back to ask whether the person giving them advice has any standing in the context of what they are trying to achieve. If you are a student looking for mentors who will challenge you, learn more about our mission to connect ambitious people with real opportunity.

What Separates People Who Make It From Those Who Flame Out

People make decisions when they are unhappy. When things are going well, they let it ride. When things go wrong, they make quick decisions. And quick decisions made from frustration are usually the wrong ones.

"Don't decide that you want to be anything until you're good at it. You don't know if you want to be an advisor or not until you're good at it. I thought I wanted to be an advisor, and then as soon as I got good at it, I said, I actually think I wanna be more than this."

Tommy was frustrated in Orlando. He was unmotivated and disillusioned. Thoughts crept in about whether he should stay or find something better. But he noticed something: those thoughts only came when things were hard. They never came when things were good.

The people who make it are the ones who refuse to make decisions from a place of frustration. They wait until they are good at something before deciding if they want more. Winning is contagious, but so is losing. You find ways to lose when you are frustrated. The path forward is to get good first, then decide.

If you want to explore career paths where your ceiling is determined by your effort, browse jobs from employers who reward results.

Never Giving Up Is a Function of Humility

Tommy walks into organizations and asks two questions. Who here has not eaten anything in the last 24 hours? Who did not sleep with a roof over their head last night? When no hands go up, he reminds them they are luckier than 90% of the people in the world.

"The secret to never giving up is humility. When people give up on their pursuit of what they want for themselves, it's actually a form of arrogance. They're not understanding how nice things are or how lucky they are."

When things feel bad, they usually are not that bad. No one is going to break your arm today. The context matters. Tommy thinks bigger than he thinks he can, ties himself to people who look like his goals, and refuses to quit because he recognizes how fortunate he already is.

His advice for young people: admit you are lost, challenge your assumptions about who you are taking advice from, think bigger than you think you can, and never give up. Without failure you have no value to offer others. Your mistakes become the wisdom you share to help other people get through their challenges faster.

Want to hear from more leaders who built careers by refusing to settle? Book a speaker for your student organization or connect with the Incubator Hub to start building your own path.

Your Questions About Leadership and Success

What are the three things every leader needs?

Trust, loyalty, and respect. Tommy Nickerson, Senior VP at Florida Financial Advisors, teaches that if you cannot confidently say your team trusts you, is loyal to you, and respects you, those are exactly the three areas to focus on. Trust is built by acting in others' best interest even at your own expense. Loyalty is demonstrated through behavior before you can expect it in return. Respect is earned by getting in the trenches with your team rather than leading from behind a closed door.

How do I find mentors who will actually push me?

Look for people who have a vested interest in your success, not your feelings. Tommy Nickerson explains that the people who love you most often give the worst career advice because they prioritize how you feel over what will help you grow. His own parents suggested he take a safe job when he was struggling. Instead, seek out people who have achieved what you want to achieve and do exactly what they tell you to do. If you want to be the best, you do not ask someone who has never done it.

How do I keep going when I want to quit?

Stay humble. Tommy Nickerson believes that giving up is actually a form of arrogance because it means you do not recognize how fortunate you are. He asks teams to consider whether they have eaten in the last 24 hours and slept under a roof. If yes, they are luckier than 90% of the world. When things feel bad, they usually are not that bad. No one is going to break your arm today. Maintaining perspective provides the foundation to persist through difficult moments.

Why do most people fail in their careers?

They make decisions when they are frustrated instead of when they are succeeding. Tommy Nickerson explains that people only consider quitting when things are hard, never when things are going well. Those quick decisions made from frustration are usually wrong. The people who succeed wait until they are good at something before deciding whether they want more. Do not decide you want to be anything until you are good at it first.

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Published BY

Jason Mickool

Jason Mickool is the founder of Take the Power Back (TTPB) ad CEO of Florida Financial Advisors (FFA), the anti-gatekeeper career platform that connects ambitious college students directly with opportunity. After witnessing countless talented graduates get stuck in traditional career paths that limit their potential, Jason created TTPB to bypass institutional gatekeepers and give students control over their professional destiny. Through direct employer connections, transparent compensation, and access to non-conformist career paths, Jason helps students transcend outdated expectations and build extraordinary careers on their own terms.