“I done been on the other side of retirement and it’s good when you get over there and you can do what you want to… So I’ll tell y’all right now while y’all in it (NFL). Take care of y’all mentals, y’all bodies and y’all chicken. So when y’all ready to walk away. You can walk away and be able to do what you want to do.” — Marshawn Lynch

In his final interview of the 2019 season, Marshawn Lynch, the twice-unretired Seattle Seahawks running back, shared words of wisdom to younger, more vulnerable NFL players. In which he emphasized that to enjoy retirement, you must take care of yourself and your finances while you’re in the league. 

As a once-retired corporate thug, in the process of transitioning back to Corporate America, I want to share my own words of wisdom to those who aspire to leave corporate and play the entrepreneurship game. 

Sixteen months ago, I boldly and daringly took a leap of faith. Exiting my secure corporate job for the rogue life of entrepreneurship. Equipped with purpose and passion, I left the Big Apple and relocated back home to the DMV.

A true inspiration to many of my peers as I was escaping the rat race. An aspiration that many talk about, but few are willing to do. With no intention of returning, I felt free, liberated. However, unknown to most, and myself at the time, that freedom came with a price — a unique set of challenges I was not fully prepared for when I left. 

Moreover, sixteen months later, I’ve decided to return to Corporate America. A statement that would symbolize failure at the start of my journey, but in this present moment represents growth. Liberation is no longer tied to being free from “the man.” Instead, it’s rooted in knowing my gift and the ability to generate income from it. 

Nonetheless, we believe you’ve Bossed Your Life Up when you’re thriving in the 5 Pillars. This journey tested and stretched me in all of them. To help those who aspire to make the leap from corporate to entrepreneurship and prevent you from making the same mistakes I did, I’m sharing the lessons I learned over the past 16 months. 

Financial Tips

Reduce Expenses:

In one of the many self-help tapes I’ve consumed, I heard this idea: buy the house you can’t afford if you are a sales professional. As it will push you and give you the extra juice to go hard so you can afford it. This philosophy operating somewhere in my subconscious informed how I handled my expenses when I transitioned.  

Six months in, I foolishly kept making my $300 federal student loan payment. I thought that by attempting to maintain my lifestyle, I’d work harder when, in reality, it just drained my cash reserves quicker. As an entrepreneur, cash is king! Do anything to protect your cash reserves. 

Even if you have the money, pause your student loan payments for at least a year. Give yourself time to get comfortable and used to the entrepreneur lifestyle. The game has its highs and lows, and when you first hop in, it’s hard to know when, how long, and how low, a low will go. What $1,800 meant to me 16 months ago is a lot different from what it means to me today. 

Also, if you don’t want to defer your student loans because you have a target payoff date. I’d still say put the money to the side and pay the forgone payments after your first year as an entrepreneur. It’s better to have the cash and not need it than not to have it and need it. 

Cash Flow Producing Assets: 

“Cash flow gives you freedom. But appreciation gives you wealth.” — Brandon Turner

If someone was going to change my family’s trajectory, why not me? Early in my corporate journey, I knew the best I could do by climbing the corporate ladder was to provide for my future wife and kids, and that wasn’t enough. When you’re first-generation wealth at minimum, it’s a four-generation endeavor. Your parents, you, your kids, and your grandkids. 

Leaving corporate was a declaration of my commitment to the journey. Naive, I missed a crucial step. I tried to go straight from corporate to wealth building when the correct step is corporate to freedom.

Having a hustler’s ambition from a young age and an interest in money, I went on to get a finance degree. During my studies I learned the two main investment strategies: cash flow and appreciation. Cash flow investments produce residual income, whether it’s a rent or a royalty check. While appreciation investments are calculated bets that the value of the asset you purchased will appreciate. It’s like investing in Uber stock before it went public. 

More importantly, appreciation investments, for the most part, only produce income when you sell the asset. While cash flow investments produce money in the interim period between the purchase and the sale.

During my time in corporate, I invested in appreciation based assets because I was chasing wealth. But by playing the long game (wealth), I neglected the short term (freedom).  Tying a lot of my money up in investments that produced no income. 

Over the past 16 months, I’ve had to sell most of my investments. Assets that in the long term, I expected to have big payouts but because I couldn’t upkeep with my current lifestyle I had to sell.

Nonetheless, if you plan to leap in pursuit of wealth building, make sure you obtain freedom first. Get some cash flow producing assets so you can generate income during the period between freedom and wealth. Income that is sufficient enough to meet your monthly expenses.

Because knowing how to make money or having appreciation based assets is not a means to quit your job. Volatile earned income and/or investment income do not get you freedom. Residual income does.

Emotional Tips

“Are you ready for what comes with it?” was the question Danny asked when I told him I was pulling the trigger and quitting. Before responding, I paused, thinking I’m ready for the hard work and long hours, so yes. 

I left fully prepared for the entrepreneurial work ethic: late nights and early mornings. However, I wasn’t prepared for the emotional side. The personal demons I’d have to face and the heartbreak I’d endure. These are some of the lessons from the emotional pillar. 

Cry don’t Complain:

“Don't cry to give up, cry to keep going. Don't cry to quit! You already in pain, you already hurt! Get a reward from it.” — Eric Thomas

Life, my process, and the pressures of entrepreneurship led me to tears a few times during this 16-month journey. Johnny Depp said it best, “people cry, not because they are weak. It is because they’ve been strong for too long.” After fighting and fighting, pushing and pushing, in many of these vulnerable moments, it felt like there was nothing else to do but release. To cry. 

Oddly, when I reflect on some of those moments in my journey, it’s apparent that I’ve become more resilient. I’ve always been a fighter, but now I’ve drastically improved my knock out recovery speed. 

At the start of my journey, I could easily waste a couple of days complaining and feeling sorry for myself. Slowly but surely, I transitioned to a day, and now it’s no more than a moment.

In the car overwhelmed by life and no longer able to mask my emotions, I turned on Been Down by Nipsey Hussle ft. Swiss Beatz, and shed a few tears while reciting the words. The next song that came on was Keep It Goin - Shy Glizzy. By the end of Keep It Goin, I was good. I pulled out my laptop and got back to work. 

Learning to release is essential to your well being as an entrepreneur. Bottled up emotions don’t help anyone. In the past, I’d complain for days instead of having a good 30-second cry. How inefficient.

When you don’t release, it’s hard to keep going. Crying cleanses your soul while complaining makes it toxic. Nonetheless, have your moment then keep it moving. Keep working and get a reward from it. 

What You Do vs. Who You Are:

“Do not let the roles you play in life make you forget who you are.” ― Roy T. Bennett

In the Victory Lap article, I shared how one week before my last day in corporate, I lost $14,000. Instead of the projected $20,000 I was supposed to make on my first real estate wholesale deal, I made $6,000.

Sixteen months later, fully removed and unbiased, I realize that while writing the Victory Lap article, I was still synthesizing that moment and how it affected my entrepreneurial journey. 

The hard truth is that I never bounced back from that moment. The abundance mindset I planned to leave corporate was gone the moment $6,000 came into my account instead of $20,000. And in its place came desperation.

The cushion that I anticipated having was stripped away from me. But more importantly, I felt like a failure. I had bet on myself, and before even exiting, it appeared to be a bad decision. 

I felt foolish because essentially, I had quit my full-time job for less than a month and a half of my salary. Not wanting to confirm my negative self-talk, I started avoiding rejection.

Even though I knew I needed to incorporate cold calling into my wholesaling business, I couldn’t. I found every way to avoid it. Calling hundreds of people and getting rejected by 95% of them was too overwhelming for my broken ego.

Also, when my mom asked, “how’s business?” being able to share the accountability helped mentally. Being able to say, it’s the investor, wholesaler, or homeowners fault made life all the more bearable. 

Nonetheless, one of the most challenging tasks to do in life is to separate what we do from who we are. A failed deal does not make me a failure. As an advocate of entrepreneurship, I’d have to draw a line here and say if you can not make that separation, then you are not ready.

I’d argue it’s the most important work you can do before leaving corporate. Entrepreneurship is the path of most resistance; it’s a path filled with rejection. As long as you associate who you are with what you do. You’ll always run from rejection, which means you’ll simultaneously be running from success. 

Self Talk:

“Watch how you talk to yourself because you always listen to yourself.” — Melvin Nunnery

The entrepreneurial journey is lonely. The beauty is the loneliness allows you to think and create, the ugly side is that if your self-talk is negative, negativity can consume you.

Poor self-talk not only distorts your vision of yourself but also of the past.

Many times during my journey, I’d think, “Nathan, why did you do this to yourself?” You had a comfortable job in NYC. It wasn’t perfect, but at least you lived under the allusion of security. Then, I’d remind myself about some of my troubling memories and how I prayed to be here. So stop reminiscing about places you hated and were dying to leave. 

In August, with no professional experience, I was at DC Start-up week, introducing myself as a copywriter. It was going well until the 9th person I spoke to. In conversation, he said, “so how did you become a copywriter because everyone calls themselves one these days.”

At the moment, I responded well. But after leaving the conversation, my self-talk became negative. Calling myself a fraud. Until finally, I reminded myself that although I didn’t have a portfolio, I was still a capable copywriter. 

Controlling your self-talk is critical. Had I let those thoughts consume me, I would have missed out on meeting future clients.

Mental/ Intellectual Tips

“Focused mind power is one of the strongest forces on earth.” — Mark Victor Hansen

Over the past sixteen months, I learned real estate, copywriting, design, SEO, and AWS Cloud, and more. This journey taught me I’m capable of learning anything I focus on. Don’t discount the power of your brain and it’s mental capacity. As long as you respect and embrace the four stages of learning, you'll be fine. 

  • STAGE #1 – Unconsciously Incompetent
  • STAGE #2 – Consciously Incompetent
  • STAGE #3 – Consciously Competent
  • STAGE #4 – Unconsciously Competent


“Mitchell J. Neubert and three colleagues at Baylor University investigated the connection between faith and the propensity to start a business and found entrepreneurs pray more—several times a week, on average—and are more likely to believe in an engaged, responsive God who takes a personal interest in them.”

My faith was a significant part of my journey. Tested daily, my faith grew and matured. Perspectives I used to have with regards to my relationship with God are different. Mainly around prayer and control. 

Initially, I’d pray for God to operate based on my master plan. Seeking some sense of control, but looking for it in the wrong place. I wanted control over the result, so I’d pray for God to handle the process, and get me the result I was seeking.

Now my prayer is for Him to reveal to me what I already have, be it a relationship or a skill set that will allow me to get His desired result. God's empowered us with the skills to control the process and wants us to give him control over the result. Now sixteen months later, I’m finally embracing the BYLU value, the process is the prize. 


"So many people spend their health gaining wealth, and then have to spend their wealth to regain their health." — A J Reb Materi

Don’t get so caught up in the grind that you neglect your health. My gym membership was one of the last things I sacrificed financially. I held onto it as long as possible. Working out has physical and mental health benefits. It allows you to not only strengthen your body but also release stress and tension. It’s a great way to clear your head, think, and recharge, so you have the energy to keep going.


It’s been a blessing  to exist and obtain a living outside of the corporate structure over the past sixteen months. As I transition back, I look forward to seeing what’s in store for this second corporate run. If you’re considering making that leap I hope this article does not discourage you but empowers you with the toolkit you’ll need to have sustained success as an entrepreneur.