Where do I take this love-hate relationship from here?
It’s been over ten years since I ventured out on my own. The rocky roads of entrepreneurship has been filled with highs and low, love and hate, certainty and mystery. I wrote a letter to entrepreneurship.
I thought I’d share my musings with you.
Dear Entrepreneurship,
I know it’s been misty. But we’ve been together like sunglasses and Ice-T. Fried plantains and jollof rice. Give me another half a decade, and we’ll be locked in for life.
It all started with a comfy job, back in Austin. You glanced at me through my desktop screen. On road trips, you lured me through the stories filled in glossy magazines. I bought them at airport stands. I updated my plans. Entrepreneur dot com. Fast Company blog posts. I stayed up with fantasies in my mind like, I can have you and keep my six-figure salary baseline, and just coast.
In my spare time, I started building websites. The first developer took our money but never delivered. I wanted to lock it in with you but didn’t make it exclusive. Built another website, just to show my commitment. You thought it was cute when I launched and no one showed up. I later found out that you had a different recipe for customer acquisition. Why didn’t you tell me earlier? I asked. You never responded. I guess you wanted to see whether my heart was really in it like I claimed.
Ready to take the risk. Ready to shoulder any blame.
I played it safe. I continued stringing you along. I went to business school, mixing business schemes and fun. I laid the foundation to build our dream life together in between classes. Some of those classes taught me and my friends how to treat you with respect. But we were young, we were just looking for checks.
But on another note. The silicon valley vacay. Put me on a different boat, where I watched your deck get flooded with waves of huge, future valuations. Down on sand hill road, where I guess I didn’t get the invitation. You looked a lot different than what I first envisioned.
I didn’t realize you had bailed from the west.
You wrote to me a few times from your new location. Telling me you struggled with long distance relationships. You reminded me that “I had to be where my market was.” I exited highway 101, departed from SFO. Almost a day later, I was in Ikeja Lagos. They told me you hung out in Yaba and V.I. It was time to get serious. You watched as I stumbled my way from one product iteration to another. The real lesson laid ahead. You asked the bank to give me a wake up call. Instead, they sent me an email saying “my bank account was low.”
That’s when I learned an important lesson in our relationship: “never run out of cash.” I was still in my engineering mode. Still building like I was in class.
You sat me down and said, “if we’re going to be serious, Nifemi you need to learn how to sell.”
Well.
I started selling. Shooting off emails to strangers. Chopping rejection left, right, and center. Getting on calls, not closing deals.
That’s when you finally took me seriously.
You were kind to me. In a few months, I closed my first deal. Two months later, I closed another one.
“It’s up and to the right from here.” I told myself.
I was so wrong.
I still had so much to learn.
Just like when I had to create an invoice for my first deal. I had no clue where to put my logo still. You showed me templates online that I could follow. When I wrote blog posts to build credibility, you showed me persuasion structures to borrow.
I sold.
Created invoices.
Managed client expectations.
Facilitated deals over hotel dinners.
Consolidated accounts on QuickBooks.
Paid credit card dues.
Traveled back and forth to manage my relationships with family and friends.
I think you got jealous because I still had time to make music and draft a manuscript for a novel.
But our bond didn’t come without sacrifice. I lost a good amount of friends along the way. That was just half the price. I missed trips and landmark occasions. I kept telling myself, “I’ll go for the next one.” But my bank account kept racing towards the bottom. This was around the same time I started hearing the naysayers. Their questions became more bold, more salient. “What have you been up to? Didn’t you go to Stanford? Don’t you know investors?” I got quieter, and spent more time with you. I made a handful of new friends. They were few and far apart, on a similar journey with you.
When I met them, we bonded about how you’ve treated us so far. We laughed, knowing we could all walk away, but we were gripped by the entrepreneurial Stockholm syndrome.
Free to go back to a job but enamored by how free you were.
At the end of the day, it’s me and you. The two of us. We’ve made it through tough times though.
You remember the pandemic? When everything went to shit? All those free webinars we put on, just to keep stoking the flame. I realized that there was a thin line between being in a relationship with you and being flat out unemployed. In my low spirits, you teased me “how about you go get a job.”
I’d responded; “haba, someone can’t even joke with you, small.”
We rode those long tides strong. We came back to the states.
The lows were draining but the highs – ecstatic. Every deal closed was a boost in confidence, I must say. We danced to James Brown every time I signed. I got soooouuul. I’m superbad.
The journey seemed to be building on itself. The growing client base. The testimonials. The bigger deals. The tax bill I neglected that came back to bite me in the yansh the year after. I projected big dreams across columns in an excel sheet. Discounted cash flows, multiples, and enterprise value. I had big exit plans and those “low account balance” pings were getting further apart.
To the moon, we go. I thought I had figured you out.
I stopped paying attention.
Until everything stopped working.
The playbooks didn’t convert. The deals didn’t close. The clients stopped responding. The road ahead was filled with woes. I apologized for my neglect. I had become too involved with myself. I thought doing more would make us reconnect. “It’s me and you in this, right?” You didn’t respond to that text. I couldn’t understand why you were so distant or what was up next. But it wasn’t you. It was the environment we were in. Interest rates. Geopolitics. Civil unrest in the east. A couple coups in the west. A few greedy leaders on the scene, puffing up their chest.
You told me to put my head up to see the bigger picture.
I didn’t listen. I thought I could power through to get right with ya.
Then I got the biggest lesson that only life could teach. It was an illness that I thought I didn’t earn. This was never in my pitch. I had no choice. I hit the brakes. I thought you were the cause. I asked the doctor: “Was it her? She’s so toxic. Did I stress myself out trying to make it work?” He responded. “No buddy, it was just bad luck.”
Fackk. What am I going to do with this? I’m stuck.
I thought you were my good luck charm. I wrote to you to meet me at the park downtown. We walked around and I said it. “I need a break.”
Surprisingly enough, you said “I understand it.”
A few months later, I was at a job. It took a few months to find. Because of you, I had been writing online. My credibility was high. The first few months felt good. Cool product. Engaging mission. Direct deposits every two weeks. No client chase-downs. It felt great to breathe.
But you still found your way to me, even in the 9-to-5. We had a side-thing going. More like a 5-to -9. Client engagements during my lunch break, early mornings, and after dinner. You were with me when I wrote, published, and sold my fourth book. I did the steady job for a year but apparently my learnings there were not deep enough. Hey, I knew I wanted to get back to you, for real, for real.
13 months after the break, I was back fully back, dedicated again.
But things had changed. Technology, once again, shifted your perspective. There was a lot of noise, new players, different trends, new rules. But deep down, I knew you had the same principle, even though you flashed new tools.
Those principles encouraged me to make moves even when things are unclear and uncertain. The one that cheered me on when I had received my 29th rejection. The one that peeked over my shoulder and told me to write more even when the words on the page don’t make sense. The one that reminds me that all that matters is how you show up in the moment.
That’s what you say: “Trust the process. The outcome will take care of itself.”
I’ve learned that it’s not about you or our relationship. Entrepreneurship, you’re just a mirror to show me who I can become in the process.
I hope you show the same love to my friends.
Yours truly,
Nifemi
P.S. Share this letter with an entrepreneur or aspiring entrepreneur. I wonder what their experience with entrepreneurship has been like.
