I lost myself on an island of self-doubt
This is an exercise in self-love.
I was sitting on a roof drinking with some friends one afternoon in college, and I overheard someone talking about a rope swing at a popular swimming spot nearby.
My ears perked up. I’d been to that swimming spot, and I hadn’t seen a rope swing. I asked for some clarification — where is this rope swing? It’s on the other side of the island? Ohhh!
In my tipsy haze I decided I was going to visit that swing. It never crossed my mind that I might need more directions.
I invited dozens of my friends to a ‘day at the rope swing’ on the Haw River. “I have intel on the location of the elusive swing,” I told them.
And for some reason, they believed me. So when a warm weekend at the end of the semester came around, a big group of us drove to the river and walked a half mile upriver to the swimming spot.
We hung out in familiar territory for a while before the instigator in me started instigating.
“Who wants to swim across and find the rope swing on the other side of the island?” I asked.
A group of five of us swam across the river. Once we reached the island, we struggled to find a good spot to climb out. The bank was steep and slippery. There was no obvious trail.
That should have been my first clue that something was amiss.
One friend managed to drag himself up by pulling on a stout weed and wedging his Chacos between the mud and a tree root. Then he pulled the rest of us out.
We bushwhacked across the island through chest-high weeds in bare feet and bikinis. A few more friends got curious and traipsed through the island on our faint trail.
They found us standing on the opposite bank, looking perplexed. There was no rope swing, and no evidence of one. Finally, one friend swam out into the river. He started shouting.
“I see it!”
The rope swing was a quarter mile away downriver. By now there were 10 of us spilled into the wrong side of the river. We had no interest in retracing our steps through the buggy and scratchy weeds.
So we started swimming.
We found a hidden paradise of fire rings, secret camp sites, a jumping platform, and a great view of the lower river beyond the nearby dam. We jumped and swang ‘til we had our fill, and we found a return route that involved no bushwhacking (but at least one close encounter with a water snake).
But the point of the story is that despite so much evidence to indicate that leading my friends into a river on only the most vague of instructions…
— is a bad idea,
— and we were lucky it turned out OK,
— I can’t count how many times I’ve done something similar again.
There was that rope swing on the river that you shouldn’t really access without a boat but we did anyway. That cliff with the churning water. That canyon in Moab where we rappelled off a small pile of rocks. That campsite we never thought we’d find on the top of the mountain in Big Sur.
That confidence? That undaunted, unbridled lust for adventure, and that trust that everything will work out?
That is pure, distilled, 180 proof, Olivia.
I feel like I’ve lost touch with that person.
I’ve hit a low point in my entrepreneurial journey.
In the process of attempting to pivot my business to a more sustainable venture with fulfilling projects and a strategy for growth, I have run my profitable freelance career into the ground. My previous clients have tapered off, and I haven’t hit the pavement to find new ones, because I’ve been working through defining my niche, developing my processes, and testing out my theories.
Everyone I talk to says stay the course. You’re not doing anything wrong. Just be patient.
I’m a talented writer. My ideas are solid, and the steps I’m taking to develop them are well thought out. Even if the data I’m getting back from my case studies isn’t confirming my hypothesis 100 percent, it’s still good data. I can still learn something from this process.
I just need to be kind to myself.
As it turns out, I’m really bad at that.
It’s strange, because a year ago, my girlfriend Nicole wrote me a note admiring me for being kind to myself. It seems that I can be very kind to myself when things are going my way. When the client work is flowing, when I feel like I’m building something, and gaining traction — I’m downright delightful. That’s when the joyful, bold and brash Olivia comes out and rallies the troops for another poorly planned adventure.
But when the work disappears and I start wondering where my next paycheck is going to come from, it’s a different story. I feel lost.
This post is an attempt to be kinder to myself. To get some perspective on the lessons I’m learning. To remember to laugh at myself more. To remember to be thankful that I’ve made it this far, considering how many times I’ve leapt into murky, churning, or freezing water just because a chubby 12-year-old made it out OK.
Last fall, I decided I wanted more out of my freelance career. Not more money necessarily, but definitely more meaning. More fulfillment. More job security. I felt like a lot of the jobs I did didn’t have much of an impact. I was writing projects for clients who just needed to check a box for marketing, but they didn’t bring me into the process early enough for me to guide their strategy and make the written piece truly useful for them.
So I wanted more control. I launched this process of trying to pivot my freelance writing career into a copywriting agency. I came up with a name (Humanicity), bought a domain (it’s not humanicity dot com — I don’t want to talk about it) and I’m working with a graphic designer on my logo.
Oh yeah, and I hired interns. Two of them. Why? Because they were both so awesome, I couldn’t pick.
Why did I think I even needed one intern? Back in the fall, when I was being all kind to myself and feeling so confident that nothing could bring me down, I decided that I needed to make a move to grow my business. I needed to bring on help so that I could pass off some of the more time-consuming projects and focus on the higher level business development and client retention stuff.
And I wanted to have more fun at work. I wanted minions to collaborate with. I pictured us laughing in the conference room, sharing inspiring articles, working on professional development together, bonding.
And it was early December. They weren’t going to start until February. Plenty of time to get my act together, figure out the logistics of processing payroll, (oh and surprise! Start paying for workers’ compensation insurance), and plan out how I would work with them.
I guess this is the part where I’m supposed to draw the parallel between jumping off a literal cliff and jumping off the metaphorical cliff of cautious business spending. I knew it would be a wild ride and that there would be surprises (not all pleasant), but I believed that it would be a smart move. I took the leap without any hesitation.
Well, February waltzed in about three months early, by my mental calculations. I was in over my head.
I spent the first week or two on a hamster wheel, trying to come up with intern projects faster than they could complete them. I got almost nothing done for myself.
Managing a team is a lot harder than I imagined.
Don’t get me wrong, we do have those moments of laughing in the conference room, and sharing awesome examples of storytelling, and pushing ourselves to improve the way we write and present our stories. We’re getting into a rhythm. We’re publishing two stories a week at medium.com/humanicity. I’m proud of the work we’re doing, even though we’re not seeing results yet.
But unfortunately, you can’t pay your bills with ‘good experience’ or ‘lessons learned.’ I’m eating my savings like Girl Scout Cookies right now.
My concerned friends, mentors, and mother tell me to look at this as an investment in my own education.
“You’re exactly where you’re supposed to be,” they say. “This is normal. Every entrepreneur goes through this. Every 20-something goes through this. Your 30s will be better.”
Damn. I have three more years before it will get better?
Entrepreneurship isn’t all sunshine and rainbows. Most of the stories out there about failure in entrepreneurship are told by the guy who finally made it. They’re all like, “I hit rock bottom, but now I’m a gajillionaire.” Those stories are nice. They’re inspiring, so they’re important.
My story is more like, “I thought last week was rock bottom, then this week happened.” My story is also important, because other entrepreneurs, if they’re going through this, need to know they’re not alone. That this is normal. This is part of the process.
I’m going to keep pushing through. Maybe, just maybe, I’ll find a rope swing and an idyllic hideout on the other side of this island.
But more importantly, I hope I can reunite with the version of me who didn’t think twice about charging into the island in the first place.
