5 Steps To Making Decisions & Staying On The Right Path

5 Steps To Making Decisions & Staying On The Right Path

It was the summer of 2005, a time when MySpace dominated the web, Gwen Stefani was everyone’s Hollaback Girl and mortgages were given out like candy. In NYC, things were just calming down after 9-11, and I, at twenty-five, was smack in the middle of my quarter life crisis.

It all began the day my father called me into his office to announce that he was closing shop and going into semi-retirement. “We can’t afford this space anymore,” he said, referring to our luxurious Madison Avenue office, “and I'm exhausted."

A million thoughts ran through my mind after hearing those words. I thought "what’ll happen to the staff? And the agents? What about the deals we're working on? What about our clients? What about ME?!" I wasn’t sure if my dad was serious about his decision to close shop, but in case he was, I wanted to be prepared. My solution? Starting my own business. Okada & Company LLC was born on July 7th, 2005, also know to me as Lucky 77. 

Back then, at the young age of twenty-five, I wasn't sure if I was going down the right path. Thoughts of doubt crossed my mind on a daily – "what am I going to do? Will I fail? Should I work for someone else? If so which company? Do I explore other industries again? Should I listen to my family’s advice to stay?" – and I often wondered if I had made a terrible mistake by going off on my own. It was the definition of a quarter life crisis.

Overcoming this difficult part of my life required much thought, research, work and help from others. I had to get past the hurdles of insecurity, regret and anxiety, but ultimately I made a decision, and I can say now with full confidence, that it was the right one. 

These are the 5 steps I took to find my path during that stressful period of uncertainty:

1. Decision Making (Mind vs. Heart)

If you're serious about being successful and want to be able to live the life you seek, you're going to have to learn how to make tough decisions. It’s a skill that must be practiced and perfected, but that once you’ve mastered it, has the potential to change everything.

The most difficult decisions are the ones you must make when your mind and your heart are not aligned. When this happens, it’s important that you take the time to consider all your options, speak to trusted people who have experience in the area you’re working on, and do everything in your power to stay focused. Then, make a decision and never look back.

For me, launching Okada & Company was scary, but luckily my heart and mind were always aligned.

2. Taking the Plunge (Risk vs. Reward)

Prior to diving fully into real estate, I explored other industries which I believed I was passionate about, including finance, fashion and music. During my years in finance and fashion, I came across a series of terrible bosses that completely turned me off to those industries. Not only did they strip me and my peers of self confidence, but they were also extremely boastful of their own accomplishments, and took full advantage of their power. The benefits I received were not worth the stress, so I moved on to music. In the music industry, everyone was friendly, amazing and passionate.... but everyone was broke, and I didn’t want to be that either. These experiences allowed me to explore my curiosities and get an inside look at how other industries worked. I didn't like what I experienced, which made it clear to me that real estate was my true calling. I also quickly realized that I couldn't stand having a boss, which eliminated the possibility of working for another firm.

In December of 2005, I took the plunge. I drove up and down the blocks of Midtown Manhattan looking for signs that read “Office Space For Rent”. That's when I saw an opening in a loft building on West 36th Street between 5th & 6th Avenues. I had never done business below 42nd Street, but after seeing that it was a decent space within budget, I said yes.

When making big decisions, it’s important to be patient with yourself. Though there’s nothing worse than being paralyzed by indecision, great ideas cannot be forced, so take your time. Once your mind is set, don’t be afraid to take the plunge. Many people have dreams and ambitions, but most of them fail because they did not dare to take the first step. Be better. Take the plunge. 

3. Trial, Error, Adjust

This section right here, is what champions are made of. It's the come-up story. You've committed, you've taken the plunge, and now, you're here to win.

As I mentioned in my previous article, I took the plunge, signed a 12 month lease, started a company, but only had six months of savings to invest, and essentially, to survive. I was everywhere doing everything – residential to commercial, East side to the West side and Brooklyn to Manhattan – I was a glorious mess.

Week after week, I worked my ass off from day to night, but still I had very little to show for it. One rainy day, I was waiting for a client who wanted me to rent his apartment. Twenty minutes passed and he was not there. I called his cell to see if he was coming and he picked up to apologize, saying he was on his way. Thirty more minutes passed and the same thing occurred. Another hour went by and the client, still, was nowhere to be seen. It was 7:30 pm, I was soaked from the rain and I had just wasted over two hours of my life on nothing. That night I told myself I would never sell or rent apartments as a realtor ever again. The minute I stopped focusing on residential real estate, my sole focus went into commercial real estate, and my business took off.

Once you've taken the plunge, you've got to do whatever it takes to survive, win, and move forward in path you've chosen. This includes learning from your mistakes, recognizing bad decisions and starting over with the knowledge you gain. Trial, error, adjust, trial, error, adjust. 

4. Flow

As per Wikipedia, “in positive psychology, flow, also known as the zone, is the mental state of operation in which a person performing an activity is fully immersed in a feeling of energized focus, full involvement, and enjoyment in the process of the activity.” I don't know about psychology, but for me, maintaining a steady flow means you're going on the right track. It's success at its finest. It's momentum. It's mojo. It's winning. Find your momentum, and find your flow.

Six months after having opened the doors of Okada & Company, I had paid my office rent bill and verified my bank balance. It was the end of the road for me, in my mind. I had spent most of my savings, and didn’t know how I would make it another day. I remember feeling extremely nervous, but once I looked at my sales pipeline, I felt an indescribable relief. I realized that I actually did have enough deals aligned to secure my rent for the next month. In that moment,  my entire focus shifted. I went from thinking in terms of how much money I was going to make from each transaction, to how many transactions I could make in a month. I went from two deals that month, to six deals a month later, to nine deals a month after that. Eventually I hit ten deals a month, a personal record, which I counted as a celebration for my tenth month in business. 

I closed about twenty-four deals since the so called “end of the road” rent check was paid that year. Most of the deals were small, but one of the deals paid me more than my entire initial investment to the company. I had found my flow, and that’s when I knew I had made the right decision to launch my business.

5. Keep On Truckin'

We were crushing it. Over the next two years we moved offices, hired several agents, and money was flowing. The new agents were closing deals and I was free to go after bigger game. I was making a solid six figure income and I was very happy. 

On September 15th, 2008, Lehman Brothers declared bankruptcy, and everyone was freaking out. Everyone. The stock market was plunging. There were foreclosures everywhere, unemployment was skyrocketing, and for us, the faucet of dealflow, money, and success was turned off almost instantaneously. Our flow was interrupted, and it had nothing to do with our strategy, skills, or experience. 

As I’m writing this eight years later, I can tell you that we’ve thrived, but that doesn’t mean it was easy. What was right for Okada & Co. eight years ago would not be right for us today, which is why learning to adapt and make decisions based on one’s present reality is so essential.  


Your path in life and in business may have ups, downs, dead ends, mountains, valleys, rivers, bulls, bears, clear skies, rainy weather, short cuts, delays, and wrong turns. You may travel in a crowd at times, and alone at times. You may come across people who travel with you or against you, for long term or only for a while. It will not be predictable and it will not be easy, but whatever your path looks like, find it, travel it, embrace it, try your best to love it, and make it epic. One day, when you take a look back at your journey, you’ll see the results of your decisions and be proud.

Article written by Chris Okada, edited by Rosa Sanchez.

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