The Ride of Our Lives

“Self-employment is like nothing else on earth,” a friend told us three years ago when the job that had brought us to Italy ended. “One month, you’ll be feeling wildly successful, and the next, you’ll be praying for enough money to put food on the table. It’s a roller coaster. You’ve got to be prepared for that going in.”

We were. At least, we were prepared to the extent that I had been as a kid plunging into the dark of Runaway Mountain for the first time, gripping the safety bar and reminding myself over and over again that the coaster had never killed anyone. (I didn’t think…) Dan and I truly didn’t know what to expect, but we were sure that self-employment was the right direction for his career. We had considered other options, prayed at varying degrees of desperation, talked the whole thing over every which way we could, and finally wrestled our fears into a shaky semblance of trust. This was what my husband was meant to do, I was certain.

That certainty came at a heavy price for me though. On the last day of Dan’s day job, we found out that he would not be receiving his final few months of paychecks, that the tenants renting our house in the States were being evicted for failure to pay, and that our Italian bank account was blocked. I kid you not. If you can stomach a bit of raw honesty, here is an excerpt from my journal entry that day:

“I don’t know what to do with the tension curled up like a thousand knuckled fists inside my belly. I want to pray, but I keep thinking about what a friend going through tough times wrote on her blog this morning: “I still believe in the power of prayer.” Well I don’t. If you believe that praying effects change, then you have to believe either A) that we are convincing God do our bidding or B) that God is withholding his will until someone thinks to ask for it.

I’m much more willing to believe that prayer is simply a good spiritual practice for focusing and connecting our thoughts with God, but I’m so not in the mood today to commune. I need answers, both global and personal, for trusting that he will have anything to do with the outcome of the tangle we’re in now.

It’s not a good place to find myself.”

I think that I worked as hard on trust those first months as Dan did at establishing his new biomechanics business. While he was wrangling website code and traveling to meet clients, I was wrangling fears as thick-limbed as gorillas and traveling my own daily—and sometimes hourly—journey out of panic. At the time, I was working as an English teacher, which helped keep us afloat… but it also tugged the energy out from under me like a cartoon rug. I worked during the hours that my little girls needed me most, and Dan’s business trips made our home life a logistical nightmare. We were exhausted and strained and frayed all the way to the core.

I’ve found, though, that this kind of desperate, minute-by-minute living is the ultimate breeding ground for miracles.  Even as expenses continued to mount—our car’s epic breakdown, a drug operation being discovered in the basement of our rental home, and the Italian government booting us out of the country… all within the first four months of self-employment (seriously, Universe??)—we always had enough. We even got Disney World, and the kind of care that I felt from God during each last-minute upswing bolstered my courage enough for me to quit my job.

We’re three years into being on our own now—Dan an entrepreneur, I a freelancer—and I’m finally getting used to the ride. That is to say, my knuckles are no longer white and I am no longer actively preparing myself to live under a bridge. I would in no way call this experience easy. Having to provide work for ourselves, to keep forward momentum and always be on the cusp of some new possibility is exhausting. That’s the flat truth of it. However, we are also sustained by this work: by the thrill of doing what we love, by the freedom of directing our own time and energy, and by the unknown heights of potential climbing in the dark ahead. We are still sure that this was the right direction to take.

A family who has been friends with us for years finally asked this week what exactly Dan does, and we both laughed in understanding because “entrepreneur” is such a non-description. It means someone who starts businesses, sure, but that doesn’t exactly bring my husband’s day-to-day activities into focus. Actually, come to think of it, there is no such thing as a day-to-day activity in Dan’s world. There is only one day at a time and whatever menial or creative tasks will advance the project he’s pursuing. Today, for instance, he’s spending the morning on the computer working on Training Lot—a platform he’s setting up to help people make and market training videos online. Later, he’s going to join a pizzaiolo friend to film an authentic Italian pizza-making process, then he’ll put the video up as part of a publicity push to get votes for a startup contest he’s been selected to participate in.

Here’s my favorite of the promotional videos he’s made so far (though I might be unfairly biased toward those two bilingual girls of ours):

We’re on a part of the roller coaster right now that I think of as the Sideways Spiral of Death—you know, the part where the g-forces are sucking your brains into outer space and you’re doing your damndest to see through the stars and avoid throwing up if possible. This is all part of the startup process. I know this because we’ve been through it several times now, sometimes successfully, sometimes not. Dan’s in the phase of trying a new venture that’s all momentum and effort and wild uncertainty, and I’m right there with him pushing past the exhaustion and clinging as loosely as we dare to the hope that this idea will be one of the success stories.

Only time will tell. It feels crazy vulnerable to be telling you all this. I’d much rather you think of us as stable and prosperous in this life we’re carving out for ourselves. I’m tempted to wait on telling you the self-employment stories until we have it all figured out (which we will someday… right?), but then I couldn’t give you the chance to be a part of them with us. And I would really value your companionship today.

Here’s how: If you took five seconds to open this link and click “like” on Dan’s video, you could help him advance to the next round of the Summit Kilimanjaro startup contest. He was already chosen as one of the top 200, and if he remains in the top 50 by Friday, he’ll be eligible for some awesome networking and publicity opportunities. He doesn’t have all the connections or financial backing that some of the other contestants are using to get ahead, but he does have a pretty great business idea, and your thumbs up would be a huge help. Really, five seconds. (If you then shared the link with all your friends on Facebook, we would both do a happy dance. Just saying.)

If any of you have struck out on your own before, I would also love to hear how the experience was/is for you. The more of us on this coaster, the more it will feel like a party rather than a death trap, non? And hopefully I’ll have a new miracle tale to share with you (quite literally!) in the near future.