Who am I?

I see two identities in myself right now, one is a man of faith and the other is an entrepreneur. Whether directly or indirectly, I feel that these two identities are in opposition to each other. I find that as I lean into one of these identities, I naturally fall away from the other. This post is my own attempt to try and understand.

For the first part of my life, I leaned into being an entrepreneur. I must have known that I was going to be an entrepreneur since I was 8. I remember reading job descriptions and taking personality tests and every time I did so I would score “entrepreneur”. Growing up, for as long as I can remember I’ve been very ambitious and powerfully motivated to improve myself. I remember going to Borders and sitting in the self-help section and reading book after book. I would come up with all of these themes for ways in which to live your life and then immediately try them out. To my friends, this must have been incredibly confusing. One week I’d be espousing about the importance of making your bed every morning and the next week I’d be developing my self-control by electing to abstain from sugar. I was relentless.

There was a dark side to this too. My intense focus on performance led me to also be intensely competitive, despite the fact that none of my peers were competitive. I remember quitting Math entirely when I graduated high school, despite skipping a grade there as well as getting an A+ in BC Calculus. I had simply decided to myself that if I couldn’t be the best at something, it wasn’t worth doing.

I’ve also had a longstanding problem with manipulating an image for my own gain. I love telling stories, and each time I would tell a story some new detail would be exaggerated. As time passed, I’d play a game of telephone with myself as more and more details would get exaggerated. Ultimately, I’ve developed such a longstanding habit of exaggerating these stories that I’ve forgotten what really happened in many of these situations.

My academic record also became another game of image management. I re-created the previously defunct Chess Club in my Senior year of High School so that I could put myself as the President on my college application. Then I brought in an eighth-grader from a neighboring middle school to pretend that he was in High School so that he could play our first board because he was the best player I could think of.

Unfortunately, I was handsomely rewarded for what I now consider to be cheating. First, I got into Stanford based on a highly exaggerated application. Then, I suddenly had parents calling me to ask for advice and respect from my peers. Almost overnight, my dating prospects reversed course for the better.

“Truthful lips endure forever, but a lying tongue lasts only a moment.”
Proverbs 12:19 NIV

Once you do this sort of thing for awhile you begin to realize that (1) It’s exhausting and (2) you are not sure who you really are. You begin to tell stories expecting certain reactions from your peers, and then when you don’t get the reactions you are looking for your first instinct is to edit the story. Since your entire life is one enormous story, you are constantly working to craft and recraft the image of yourself, all the while feeling like it is never safe to reveal who you really are. Ultimately, being known for your true self as a fundamental need for every single human, and I had spent my own life denying this need.

I love my wife, Emily so much because she has been able cut through all of the BS and find the person who I didn’t even know I was. When I met her, to be honest, I was dating another girl and so I (unusually) made no pretenses about trying to impress her. I had just became a Christian and the girl I was dating at the time was taking a break from going to Church. So Emily became my thought partner on a bunch of sermons about basic Christianity stuff.

Emily and I also went on zero nice dinners while we were dating. In fact, I remember on our second date I asked Emily if she was interested in going to Marlowe, but she instead opted to get cheap Duck Wonton noodles at Jade Cafe. To this day, our dates mostly involve going to get cheap Chinese food and then grabbing a bubble tea / donut / frozen yogurt afterward. We pray, eat heartily, and talk in between mouthfuls. It’s simple but it means a lot to me.

Even after getting to know Emily, I was still checking boxes and keeping up with appearances in my spiritual life. My CG time became a session for humble bragging. The rules were (1) you were allowed to confess sin, so long as that sin involved not praying hard enough for others or studying God’s word enough and (2) you were never allowed to discuss anything more than that, unless you had already achieved victory over it in which case you could talk about whatever you wanted.

I want to break both of those rules right now and talk about my current problem. I’m lonely. I feel like I’m not understood and that I can’t be real. The problem is, again, that I feel like I have two identities. One part of me is the part that I just talked about, the entrepreneur. However, I only shared the part that I think it’d be easy for the reader to understand. There is a whole other dimension in which my work can sometimes feel unbearably difficult in ways that are difficult to explain and mostly unappreciated by the Christian body.

Maybe an example will do some justice. Imagine that you are an employee and company has layoffs. Several of your best friends have already let go, and it you are not sure if your job is safe or not. You are upset at the company for being “ruthless” and all about the bottom line. You have to manage the stress of knowing that your job is on the line, the grief of your friends, and your own beliefs about your employer being a money-centered pig.

Now, imagine that you are the owner of that company. You had to fire several of your best salespeople because you discovered that they were engaged in unethical behavior, but you can’t tell anyone that because they have invested years of their life into your company and are depending on you to find their next jobs. You were worried that by firing those people you won’t be able to hit your numbers, so you spent a month going back and forth with yourself making that decision. You will then have to explain the underperformance to your Board of Directors, who see you as a statistic and have their own lineup ready to replace you. You will then have to hype up the company to make sure the team stays motivated and doesn’t immediately jump ship once they realize that the company might be in financial turmoil. You are not sleeping, not exercising, keeping a lot of secrets, and your employees hate you.

I would call this a fire and would confidently say that this sort of thing happens every few weeks. If you talked about every single fire that you went through no question others would see you as a curmudgeon, and besides that, someone might hear all of that and then tell you something trite like “in my own experience, these kinds of things make you stronger.” Excuse me, did you have that experience?

Things like this make you ask other kinds of questions. Am I arrogant for out-sharing others in the group? Am I insensitive for discounting the fact that not praying / reading the scripture is a real problem? Am I prideful for thinking that I am different? These are tough questions to answer, none of them are exactly true or false.

It’s easy to avoid these questions. For example, I could decide to pursue a community of entrepreneurs. There are many, especially in San Francisco, and everyone there will guaranteed have the same brain as me. They will get it. You don’t build companies for the glamour, or to put 0’s at the end of your net worth. You’re like a parent, building a family for your children, despite the fact that your children will hate you from ages 5 to 25 before they themselves become parents.

“Simon Peter answered him, ‘Lord, to whom shall we go? You have the words of eternal life. We have come to believe and to know that you are the Holy One of God.’

  • John 6:68-69

The problem is that we really do need spiritual community. At least I know that I do. I would rather die than cut out Jesus from my life, because my previous life without Jesus was simply not worth living. There was no meaning. I could go after any achievement I set my mind to and whether or not I achieved it I’d still feel exhausted and unfulfilled. That’s not life. Life is knowing that God loves you no matter what and that no matter how much you screw up, he will always carry you to victory. He will cut through your BS and reveal the better part of you that you don’t even know exists.

“A double-minded man is unstable in all of his ways.”

  • James 1:8 KJV

I want to pursue an integrated life. I don’t know what this looks like. But maybe what it starts to look like is finding other Christ-Centered Entrepreneurs. Maybe it’s being vulnerable with my existing communities and asking for help. Probably it involves smashing some of the distortions that are splitting who I am into two pieces. Probably it will be hard. Probably it will take time. Probably years. Hopefully it will be worth it.


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