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Leaping, trusting, and breaking the internet: Lessons in being an entrepreneur

After 27 different jobs and over 20 years of working for other people, I recently opened my own business. I am still getting used to the moniker of entrepreneur or founder, and instead feel like crazy, lucky bastard may be a better title. Having just burned out in the nonprofit world and looking for change that would allow myself and my family more flexibility and a real quality of life, I quit an excellent job with great benefits and needed a sabbatical of sorts. After a small dalliance into the local tech scene where my aging black MacBook got me the strangest looks, but where  I learned amazing things, I finally got started on my break and on launching Me, 2.0.

I spent a month and half getting up later, exercising more, writing, playing music, watching people, contemplating, and worrying. And all the while I was applying for all these great  jobs that whizzed by my me on Mac’s ListPDX Pipeline and on the #PDXjobs hash tag. Frankly,  I was not having much luck with the job search either, because I am not a specialist. I am what we would call a glorious generalist: I am good at many little things, and not an expert in one single one. I needed a gig that took advantage of that fact, cause it seemed like Nike, Adidas, Intel, and all those dozens of startups and boutique agencies I applied to just seemed to pass me over. Well, only I knew what they were missing.

So I did it. I’d had a small side-business for four years, the result of teaching businesses in Colorado and Oregon about web, communication, social media and the like. There it was, right in front my face, I just had to pick up and wave it around. So I jumped. I put some effort into it. I finally got business cards and updated my website. I made Facebook and Linked pages for my business, and I reached out to my own network earnestly saying,  ”Hey this is me. I am really doing this”.  I had to ask for help too. Thank god my wife believes in me, and for the parent or two who saved us from eating too much ramen, rice and beans. It was scary… and thrilling. And then a funny thing happened: A friend knew a friend; an old company referred someone; and one of the first of the over 40 jobs I had applied for, months ago, finally called back wanting to contract with me. Within a few weeks I had real clients. I was doing it. So here are the lessons i learned as I try on this new role as entrepreneur:

1. Do What You’re Good At

Seems obvious, but really it’s hardest to be that honest with yourself. So you’re good at telling a story? Call yourself a storyteller. Good at writing about food? Then just do it! I was good at tweeting and posting for small businesses, and getting them set up and running all on the platforms. I was good at paying attention to what was happening and making it look like they were too. Well, that’s all a plus. My morning ritual of Feedly feedsand Flipboard scanning is now part of my actual job. And I always wanted to be a writer too, now, I really do get paid to write.

2. Push Your Abilities

Here’s the thing about most smart people: They can figure it out. If I don’t know how to use your CRM or email software or christ, whatever new social media widget just hit the market, I will in a week. Trust your own abilities to figure this stuff out. It’s not rocket science, and it’s really, really hard to break the internet.

3. Put Time Into Yourself

What’s the old saying; the cobblers’ kids have no shoes? A friend and I joked earlier last year that we needed to adopt Google’s 20% time for our own businesses. He’s a web developer with a shoddy website and I was a communications guy with underdeveloped communications plan. We agreed that we both needed to both take a week and just focus on our own websites and plans to build them up. And then we laughed and went back to work on other clients. But by taking my own mini-sabbatical and taking the time to focus on my own business, what it meant to me, and where I wanted to really be,  I created something that I could be proud of.  And yes, I still do need to take that week and redo my website. As soon as this entrepreneurship thing calms down….

4. Make Connections

I sent a lot of meeting requests out. I got responses from about half, most through using a deft combination of Twitter stalking, LinkedIn profiling, and internet magic. What worked even better was a simple Facebook posting letting all my family and friends know that I was in business. Well, that and handing a lot of cards out at events like TMM networking nights. Thing is, you never know who might know someone else in need. Networking events can really be a drain, but you do get good at pitching yourself while slightly inebriated, which really helps your confidence.

5. Ask For Help

We all need it, and pride often keeps us from asking, but get over yourself and put it out the world to your friends and family. Social networks exist for a reason, and people are social creatures and also  like to feel useful. Be kind and honest,  and if you are sincere folks really do want to help you. Help comes from where you least expect it too. A couple of my dearest friends offered manual labor opportunities so I could at least pay my bills and eat while I started up my company. In fact, the one that had the least ended up paying me the most. How’s that for a little lesson in humanity?

6. Leap

At some point, you just have to close your eyes and jump. Trust yourself and a net will appear. It just might not look like a net.