What I’ve Learned Since Leaving My Dream Job

One year ago, I left my dream job.

I say it was my dream job because I loved the work, had great relationships with my clients and made a sizable six-figure income. As long as I stayed, our family’s future was secure. We had a financial advisor managing our long-term assets, our short term needs and wants were completely covered and we were able to give back. We had everything we had ever dreamed of.

But the truth is, my dream job had become just a job.

I loved the work, but I was handcuffed to comfort. And as much as I wanted to deny it, there was something imbedded in my DNA that wondered if there was more to life than comfort. I guess it took me achieving my dreams to understand that you should never stop dreaming.

To break the cycle, I had to see if I was still capable of doing something that scared me. So, I turned in my resignation.

The past year has been humbling to say the least. It has been a lot harder than I thought it would be. But at the same time, there have countless moments that have provided a deeper sense of understanding, renewed perspective and a much clearer focus in life.

Here are a few things I have learned that will help you on your journey.

Money Isn’t Motivation

I’ve never known what it’s like to be destitute and poor, so I won’t pretend to understand how that feels. To a man with an empty stomach, dirty clothes and a broken spirit, a few hundred dollars can provide something to eat, a clean outfit and hope that there’s life beyond poverty. In that sense, money is good.

But money is also dangerous. One day you’re focused on how much more you need and they next day you’re driving yourself crazy trying to figure out how to protect what you already have.

This year has helped me come to grips with the truth about money. Money can do a lot of good. But if money becomes your motivation, it clouds what truly matters and comfortably sings you to sleep.

Please God. Love People.

People are difficult. They’ll praise you one minute, then criticize you the next. They’ll promise you the moon and then fail to keep those promises. Because of that, I spent a good part of this year angry at people. The problem was, I had the wrong perspective.

I began this year as someone who lived to please people and love God. That seems good on the surface, but it’s exhausting. It took brutal honesty, a few painful situations and many difficult conversations to realize that I had it backwards.

Please God. Love people.

People Are Your Greatest Investment

As difficult as people are, people are also the greatest investment you can make. 

In the past year, I’ve individually connected with more than 1,000 people. Some of those conversations have grown into connections. Some of those connections have grown into relationships. And, some of those relationships have born fruit.

The point is, every person you encounter is like a seed. They have the potential to bear fruit. It’s not our job to demand the fruit of the relationship. It’s our job to nourish the seed and trust that God will use it as He desires.

Stop focusing on the outcome and invest in people.

Let Go of Who You’re Not to Become Who You Are

Some things are so deeply ingrained into our identity that it’s impossible to see ourselves apart from them. But there’s great danger in defining yourself by what you have and what you do. It begs the question, where will you be when it’s gone?

The critic says, “What am I supposed to do, lose everything?”

No. You don’t have to.

But, if you’re unwilling to let go of what you have or what you do, those things will define you.

Let go of who you’re not and you’ll begin to discover who you truly are.

Never Overestimate Yourself

Hubris is subtly destructive.

As an independent contractor and successful sales guy, I thought it would be easy to start a business. I was wrong. This year has taught me that I have a tendency to overestimate myself.

Remember, the Titanic was unsinkable until it sunk.

Inner confidence is necessary. Self-confidence is destructive.

Never Underestimate God

You’ll never know how good God is until you completely surrender to His will.

A year ago, I loved God with my whole heart, but good things like money and people and careers and even my own self-image blocked my view of His plan for my life. The bottom line is, I didn’t understand how much He truly loved me.

I thought God was a puddle that I could playfully splash in. Now, I see that He’s an ocean of goodness that is majestic and unsearchable.

The only thing holding me back was my fear and my limited understanding.

Where to From Here

The road ahead is very, very exciting.

Despite the difficulties of personal growth, the month of June was the most rewarding month in our company’s short existence. 

We continue to walk with an increasing number of people in our daily text community, our one-to-one biblical counseling, faith mentoring and executive coaching services continue to bear fruit in transformed lives, speaking opportunities and leadership development events have picked up. And, through our non-profit initiative, The LIFE Center, we were able to protect a family from foreclosure by fully covering their mortgage payment.

In my recent TEDx talk, I shared a quote that Kevin taught me—a quote that is a cornerstone for our business and ministry.

“The gravity of comfort is mediocrity.”

If you’re feeling handcuffed to comfort or handcuffed to mediocrity, I’m here to tell you that there’s more. And the key that will set you free is your willingness to step in—to press into the discomfort.

It won’t be easy. No great adventure is.

But it’s worth it.


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