A Successful Entrepreneur Explains What It Takes To 'Reinvent Yourself'

Jason Tartick reveals his secrets to successful career reinvention, strategic risk-taking and personal branding.

By Mark Travers, Ph.D. | March 04, 2025

In the world of career pivots and reinvention, few have navigated the transition as seamlessly as Jason Tartick. Once a corporate banker, Tartick made the bold leap into entrepreneurship, financial education and personal branding, ultimately turning his expertise into a thriving business.

According to Tartick, however, reinvention is more than just choosing a new job or industry. To him, it entails redefining fear, raising personal standards and crafting a brand that truly reflects who you are.

I recently spoke with Tartick about what it takes to make a bold transition, overcome psychological roadblocks and set yourself up for long-term success. Here's a summary of our conversation.

Leaving a high-paying corporate banking job was a massive leap. What was the psychological turning point that made you take that risk?

While I valued the near decade of time I spent in banking, I always knew it wasn't my end-game. As a result, I approached finances with the same strategic mindset that had guided my corporate career. By maintaining disciplined spending and budgeting, I positioned myself to take a calculated risk—one that allowed me to pivot with confidence into entrepreneurship.

From 2010 until 2019 I worked in the banking industry, serving in roles aligned with underwriting, strategy, and mid market lending. In 2019, my last role at the bank was a Senior Corporate Banker. I am a big advocate for salary transparency, so in that role back in 2019, I was earning a $165,000 base salary, with a $110,000 signing bonus and a potential annual bonus based on performance.

In what was an absolute shock to me, in 2018 and 2019, my earnings from social media surpassed my corporate banking salary. For the first nine months of monetizing my content, I consistently out-earned my role as a Senior VP in corporate banking, month after month. The information provided comfort in my decision, yet the risk of the unknown and security in the space was certainly daunting… especially in 2019.

Many people stay in careers they don't love because of stability. What advice do you have for someone who feels stuck but fears change?

The average professional will work for 40 years in their lifetime, 480 months, 2,087 weeks, 14,610 days. I spell these numbers out intentionally because of the way our brains process them.

At first glance, you might think, "Wow, that's a lot of time." But the way I see it? We have 40 years to channel our energy, creativity and livelihood into something meaningful—something that creates impact, drives change and builds a legacy beyond just ourselves.

I don't see these numbers and think, "That's a long time to work." Rather, I see them as a challenge: "How can I turn this time into something greater than me?" The sooner we shift into that mindset, the sooner we can unlock our full potential. And what stands in the way of that shift? Fear.

The coffee in my hand has more reality and substance than fear. Fear is a construct that influences our behavior, rewires our brain and limits our decisions. But at its core, it's nothing more than an idea. To let a fleeting thought—one that is made up—drive and dictate our potential life's work? That's what's truly terrifying.

No matter what you do, your work has the potential to outlast you. It can extend beyond 40 years, beyond a generation. Whether you're an entrepreneur or working a 9-to-5, there are always ways to use your resources to create something bigger than yourself, such as through a foundation, mentorship or innovation.

But fear—an empty thought that can truly impede anyone, any day and for a lifetime if not overcome—is just a thought or an illusion.

Your career shift was very public. How did you handle the external pressure and opinions when making such a bold transition?

If there's one lesson I've learned, it's this: never take advice from someone who hasn't been where you're going. Be cautious about absorbing guidance from those who haven't walked the path you're on.

Back in 2018, telling someone you were leaving a stable corporate banking career, after nearly a decade of climbing the ranks at an accelerated pace, to become an "influencer" was nothing short of absurd in most people's eyes. The idea of pursuing digital media full-time, especially after launching from reality TV dating, seemed downright asinine to many.

Fast forward to 2025, and while the creator economy continues to expand every year, most people still don't fully understand it. Back then, nearly everyone, especially those at the bank, assumed my career move would fizzle out in six to 12 months. Quite honestly, part of me thought the same. They couldn't wrap their heads around the idea that this was a viable, long-term business.

And yet, here we are. 2025 is shaping up to be the most financially successful year yet. Ironically, the way I've built everything—my podcast, books, agency, management company, investments, speaker series—was fueled by the skepticism I faced early on. That judgment pushed me toward financial transparency, challenging the doubters. I would sit down with them and show them the analytics, impressions, link clicks and earnings…

Their reactions made one thing clear: there's a massive business opportunity here.

It's interesting that financial transparency was my outlet when dealing with the pressure and opinions from others. And the very concept is what leads to the driving force behind my books, podcast, content, etc. The fact that I had to openly explain it, because no one understood how I was generating income, proved just how little visibility existed around creator finances.

This judgment made me realize that we need to have this conversation publicly. The silence around financial transparency only benefits those at the top. Fewer people understanding their market value means less negotiating—which, in turn, creates more control and profitability at the top.

Assessing risk when making career and financial decisions can be a fine line to toe. Do you think of yourself as a risk-taker, or is it more about calculated decisions for you?

I consider myself a risk-taker and when it comes to decision-making and strategy; I often leverage game theory.

In basic terms, it's simply a strategy to make a decision or move when others are involved and making decisions. It also incorporates the study of strategic choices where one person's decision not only affects their own outcome, but also impacts others.

The core idea behind game theory is that there's no such thing as a perfect decision, only probabilities of impact and a range of potential outcomes based on future choices. Applying game theory is a balance between inherent risk and calculated analytics—understanding that every decision carries risk, but the key is evaluating the potential return on that risk.

This intersection of risk and strategy is something I apply daily. I always joke that my MBA was the most expensive waste of $120K because, in reality, the biggest ROI came from the network and being able to say I have an MBA. But if there's one concept I do actively use in my life and business from my MBA, it's game theory and strategic decision-making.

You emphasize financial literacy as a tool for personal empowerment. In what ways do you think money management affects confidence and mental well-being?

I believe the relationship we each have with money is analogous to our relationship with success, failure, trauma and personal challenges. No two relationships are the same, just as every individual is a unique puzzle piece in this world, our experiences with money are deeply personal.

The intersection of confidence and mental well-being arises with money when we adopt one-size-fits-all approaches to how we should relate to money. This often leads to instinctive judgments, weaponization and shame.

In my view, every relationship with money deserves understanding before judgement. We must acknowledge both aspects and shift our focus toward the positive. If we can do this, we will then feel comfortable to be vulnerable and talk about where our financial struggles are happening. This transparency is what leads to resolution.

In this society, we tend to assign a 'correct' relationship with money—but instead, we should focus on extracting the positive aspects from each approach and honing in on them. Build off the positivity of health financial behaviors, find comfort in speaking about the areas for improvement and implement change.

Each of us has a unique relationship with money, and that relationship affects all our decisions. Our financial health impacts our mental well-being, our sense of security, our freedom and even how we love and interact with others. Yet, most of us don't take the time to truly examine what our relationship with money looks like, or how it shapes our lives.

What are some psychological roadblocks that keep people from taking control of their career and finances, and how can they overcome them?

There are three:

1. Identity. Many people lose their sense of self by conforming to the identity their company wants them to adopt, rather than embracing the identity they inherently possess. It's often this unique, authentic identity when magnified, that leads to true success within a company. The key to thriving within an organization is understanding and amplifying your own individuality.
2. Branding. I always encourage people to identify an individual or public figure they admire and select three words that define their brand. I then ask them to do the same exercise with their own brand. Interestingly, most people don't struggle with identifying the 3 words for someone they look up to, but they struggle to find the three words that represent their own brand. We often focus so much on how others perceive us, rather than understand how we see ourselves. When we work within organizations, we often forget that we are also our own brand. By focusing on developing and honing that brand, we can showcase our unique value in a way that fosters growth—even in our darker moments. This deeper connection to our personal brand creates more value both internally and externally.
3. Expectations. I once spoke to 30 NFL players and asked them what the difference was between college football and the NFL. Their answers were surprisingly similar: "The game is just a little faster, and the players are a little stronger." Every year, we see new records being set, some of this is due to technology, but much of it is because expectations are continually raised. In our careers and finances, we often underestimate our true potential by setting limited expectations. When you increase your expectations, both consciously and subconsciously, you shift your mindset—which leads to greater motivation and momentum. In our careers and finances, by setting higher expectations for ourselves, we can create positive behavior patterns that ultimately lead to greater success, both personally and financially.

If you could give one piece of advice to someone considering a major career pivot, what would it be?

Once you've made the decision and closed that door behind you, resist the temptation to look back—no matter how enticing the past may seem.

There's a reason you made the choice you did, and with any significant career change comes a multitude of challenges, emotions and uncertainties. As cliché as it may sound, the key is to simply move forward.

Take action, even if you're scared, uncertain, lonely or anxious. Embrace the journey with enthusiasm, joy or whatever emotions arise. Once you make that commitment, push forward without looking back.