Be Careful What You Wish For

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When I was in high school, I dreamed of being a modern nomad.

I imagined moving from place to place on a whim (or for a new opportunity), never being tied down to one city or one person for too long, always antsy and ready for the next big thing.

Well, it turns out that I’m now sort of living the life I imagined when I was 16. The move into Manhattan was temporary, as it turns out, and though I’m commuting in everyday, I’ve now moved 7x since graduation. I’ll be at my current home for two months, and then off to Afghanistan, China, (and perhaps Jordan, it’s looking like?) before finally – hopefully – settling down into a home of my own.

Until then…

“Failure Will Happen”

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“When I am asked how to avoid failure I say that you should hire optimists. Why? Because failure will happen. It is the natural, normal, and valid result of pushing the boundaries of what is possible to scale from pilots to real impact. If you are not failing, you’re not trying hard enough, and you need optimists to recognize that failure is the mark of innovation and risk taking – key to growth and actual social and economic development that we all espouse to achieve.”

-From 9 Lessons to Learn from Faile Faire UK 2012 http://www.ictworks.org/news/2012/07/23/9-lessons-learn-fail-faire-uk-2012

Don’t Start A Business in a Vacuum

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A couple of weeks ago, I headed to the glitz and glamour of the Hamptons with R and his work family. They too were working on a start-up, and the boss invited the key leadership and their fams to his beach house in North Haven. As I watched them seamlessly blend work and play, I realized that my independence – the very reason I had quit my job – was contributing to my start-up slump.

The toughest part of being a solopreneur is the lack of accountability. Of course client-work has deadlines, but not all of your tasks will be client-centered. In fact, most will not. What about your pitch decks, business plans, networking, proposals, and professional development? How do you keep on track when there’s no one to report to?

It’s still a work in progress, but here are some of the lessons I’m learning:

  1. Schedule at least one phone call or meeting a day. Especially if you’re working from home, freelancing, or have a lot of solo work, meeting another human being provides a much-needed reprieve from your self – as well as a hard deadline. Meetings often start with “How have you been?” or “How was your day?” and even that tiny bit of updating is powerful.
  2. Find an “accountability buddy”. Look for someone that also needs some pushing to accomplish their goal, and schedule regular check-ups to keep each other accountable. Justin Koufopolous, for example, is my write-accountability buddy. We send each other friendly (usually) reminders when one of us hasn’t written for a while, and ask for honest, critical feedback on new pieces.
  3. Figure out what kind of support you most need, and build that support system. While it’s always good to have dissenting voices and hard critics, understand the personalities that you best mesh with and the type of feedback you need. Sometimes, well-meaning friends and family that think they’re helping are actually toxic. You don’t need to cut anyone out (unless it’s really gotten that bad), but be clear about your needs. It’s perfectly fine to say, “I’m not looking for advice right now, I just really need you to listen.”
  4. Work in group settings and on group projects whenever possible. Whether in a co-working space, on a client project, or just an ideas-sharing session with friends, the energy and dynamics of the group are inevitably going to be different from your own – and sometimes can lend you that extra burst of motivation when you need it.
  5. Consider – or reconsider – whether you should be doing it alone. There are ways of bringing people on board without giving up coveted equity or spending a lot of money on monthly salaries. Interns, for example, are a great way to start – though managing an internship program and getting maximum productivity out of your interns is not an easy task either. Another option is hiring commission-only, to start.

Of course, you are ultimately responsible for yourself, and to yourself. Building a business takes a HUGE amount of discipline and commitment (so much so that sometimes, I’m afraid that I don’t have what it takes.)

But for those of us that are only human, don’t start a business in a vacuum.


Mapping military influence, censoring Americans, + more

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This week, I’ve been watching (thanks in part to the awesome PD+ premium subscription service) some pretty interesting world/tech events. Here are some of the most interesting links:

Meanwhile, U.S. comedian Tosh.O attacks an audience member by inviting the audience to imagine her getting gang-raped, leading to well-deserved fury from many sides. This thoughtful response from a fellow comedian is one of the best. A choice quote:

“Your job as a comedian is to take us through pain, transcend pain, transform pain. And if you don’t get that, you are a fucking bully, and I’ve got zero time for bullies.”

Links I Liked: Redefining our conceptions of work

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My favorite reads this week are all about work – defining/redefining what it means to work, how we think about productivity, the role of the millennial in all of this, and the changes in the demographics of “workers” in the start-up world.

I’ll let you come to your own conclusions, but my take? It’s a good thing that we’re continuing to question the status quo when it comes to work. After all, we spend more time working than any other activity when we’re awake.

But then again, that’s what some of these authors are arguing against.

1) In response to this video that I originally loved, an “Open Letter from a Millennial: Quit Telling Us We’re Not Special“. Great, great points that have changed my viewpoint completely – and given me some perspective on how privileged I actually am.

2) The Busy Trap is my new manifesto. The author’s description of his day to day is my dream life (minus the ogling girls part):

I am not busy. I am the laziest ambitious person I know. Like most writers, I feel like a reprobate who does not deserve to live on any day that I do not write, but I also feel that four or five hours is enough to earn my stay on the planet for one more day. On the best ordinary days of my life, I write in the morning, go for a long bike ride and run errands in the afternoon, and in the evening I see friends, read or watch a movie. This, it seems to me, is a sane and pleasant pace for a day. And if you call me up and ask whether I won’t maybe blow off work and check out the new American Wing at the Met or ogle girls in Central Park or just drink chilled pink minty cocktails all day long, I will say, what time?

3) And similarly, an article in The Atlantic, “In Praise of Downtime” responds to the great piece “Why Women Still Can’t Have it All” by arguing that the whole system of overwork (and underemployment) in the United States needs to change.

4) Inc.com had a really interesting infographic on the changing demographics of entrepreneurship. Worryingly, there were more female founders in 1996 than in 2011.

 

Side Hustling and the Freelance Revolution

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There’s something about long bus and train rides that facilitates the act of doing nothing. Maybe it’s the hypnotizing tumble of the train car, the homes and lives that we zoom past, or the transient nature of all journeys, but whenever I sink into that train or bus seat, no matter how comfortable (or not), I know that I’m about to have a long and honest conversation with myself.

And I’ve had a lot of time to think and converse these past few weekends as I traveled to and from my temporary staffing gig at the JFK International Airport’s Duty Free Americas store. I was the Remy Martin girl, and my job was to look pretty while offering free tastings of fine French cognac and promoting the exclusive limited edition Cannes Film Festival VSOP.

Ads in the airport make a big deal about the “35 minute only commute!” from JFK to Manhattan on the Long Island Railroad (LIRR), but let me tell you, the commute tends to run much longer.

And on one of those characteristically long rides home yesterday, I started thinking about what was next after this gig. Because let’s be honest, I have no idea when I’m going to make enough to live on through my start-up alone. Maybe I could find a waittress-ing or hostess-ing job? Maybe I could finally take some bartending classes and be a bartender? (That’s something I’ve wanted to do since postponing college for a year to stay in Spain.)

And then I had an alarming thought – is this why I quit my steady consulting job? The reason that I stopped working for retired generals and ex-Navy SEALs? The result of my ridiculously expensive and somewhat elite / elitist private university education?

The answer, when it came, was surprisingly obvious -

HELL. YES. 

And here’s why – I have full ownership over everything that I do. I’m not shuffling papers just to fill up 8-hour days or performing menial tasks to help someone else check off boxes on his or her agenda. If I make a mistake, I know that it was my mistake, and I’m more than happy to deal with the consequences. Even if I end up bar-tending for the next six months or a year, it’s another life experience and another step for me to reach my goals and live the life that I want. That makes it worth it.

And I know that I’m not alone in this shift of priorities.

At PDF12, Sara Horowitz of the Freelancers’ Union spoke of the “freelance revolution” as the biggest change in workplace organization since the Industrial Revolution. She argued that ore and more people would give up the stability of “traditional” 9 to 5s and join the ranks of freelance and contract workers. Meanwhile, Tim Kreider writes in his beautifully argued op-ed, The Busy Trap that Americans force ourselves to be busy to pretend to lead a purposeful life, and that perhaps instead of this model, every American should just get paid regardless of what he/she actually does – or pretends to do.

It’s a revolutionary thought – and exactly how I feel of late.

But until that day comes, viva la revolución… y el side hustle.

Laughter and soul-baring

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I used to think that the deepest form of connection was the reciprocal baring of souls.

But this is a deeply flawed metric. It’s surprisingly easy to open up and tell all to someone that you believe that you’ll never see again – it’s much harder to do that when you genuinely care about the reaction.

I’m increasingly convinced that the true depth of connection is measured by laughter – deep, addictive belly laughs of the ROFL type. The type of guffawing that, like an earthquake, sends periodic aftershocks long after the moment itself is over. The type that you just cannot hold in, no matter how inappropriate the situation is.

Being able to laugh together – and of course, to admit what it is that you find funny in the first place – requires just as much vulnerability as traditional soul-baring, if not more. In fact, it is another form of it – what we laugh about reveals a lot about who we are.

And it’s far more effective. After all, at the end of the day, who would you rather be around – the one that you laugh with, or the one that you cry with?

Moments

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The last few weeks have been hard.

First there was the personal stuff – the big move, the towed car, the relearning to live with another person and two cats in a small space.

Then there was the professional – I’ve learned through small wins and big mistakes how to (or how not to) run a marketing campaign, taken on 4 additional social media accounts without 4 additional sources of income (or close), and asked myself again and again what I’m doing with my life and why.

The closest thing I have to an answer is this photo above. It’s these small moments, when the sun is shining, my office is my Ikea couch, and my coworkers are two sleepy animals, that make it worth it.

THIS is why I quit my job to do my own thing – to work where I want and on my terms.

So let this photo be a reminder: I wanted this freedom – and all the uncertainty it entails.

The Startup Curve

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It’s another muggy day in New York City. Police sirens scream their way down Lexington Ave. The city’s “summer stench” wafts its way up to the apartment. Internet, “borrowed” – is still sporadic, but mostly slow. Business is as well – there are awesome projects that I’m working on and so many great opportunities, but little that results in cash flow. I’m not even “ramen profitable” yet, and in this city, that’s a problem.

If Impassion Media were on Paul Graham’s startup curve, it (and I) would probably be somewhere between the wiggles of false hope and the crashes of ineptitude. I can’t decide if I’m relieved that I haven’t sunk into the trough of sorrow, or afraid that that’s coming next…

And yet… I’m still hopeful. My initial reaction to models like the one above is to reject them. (I think that’s the anthropologist in me fighting for the uniqueness of individual stories and case studies.) But on the other hand, understanding my downs as something normal and, more importantly, conquerable, is comforting.