Lessons of a Reluctant Entrepreneur

June 24, 2009
By Lisa Barone in Online Marketing

Last Friday, Rhea and I headed into Albany to attend Social Media Breakfast, a local event Rhea was speaking at alongside Mike Germano and Stuart Foster. While we were there, we met some incredible new friends. People who were excited to learn about social media and the potential benefits it could have on their business. Rhea, Mike and Stuart were there to share tips, strategies and their own experiences. I’m probably biased, but Rhea totally rocked it.

After the presentation, we got to talk to many of the attendees. We talked shop. We talked about Troy. We answered questions. One natural question everyone had was, “How long has Outspoken Media been together?” I realized in that moment that it will soon be six months. Six months since Rhea and I threw caution to the window and began writing the true story of Outspoken Media. I thought six months sounded like a good amount of time to stop, sit back and reflect on lessons learned. Plus, I head to Canada  tomorrow to spend 12 days with Rae. I may not survive.

In case you missed it, we’re in a recession. And yet, people are saying that right now is the perfect time to start a business. And if that’s the case, I wanted to share some of what I’ve learned about myself, about being an entrepreneur, and about waking up every day and not having a “job” to go to.

Here have been some of my lessons in being a reluctant entrepreneur.

Work when it hits.

The majority of my work is highly creative. I write. I blog. I tweet. I engage. I build. And that’s not always something that you can force. In order for me to stay efficient and to always have something ready to go, I need to work when the fire hits and not stop until the flame has died. Usually that means there are a few nights a week where I’m pulling days that don’t end til 3am-4am. But I need to do that and I’ve actually come to enjoy it. There is nothing like those nights when you’re on fire. When you’re on your 7th cup of coffee and Twitter is quiet because even the folks on the West Coast are in bed. Those are the days where I’m able to knock out client work plus 4-5 long posts that I can schedule for later in the week. It’s the quiet moments in the middle of the night where I’ve done some of the stuff I’m most proud of. And I know that if I don’t take advantage of those days when the flame is strong, that later I’ll regret it when I can’t write my way out of a paper bag.

When the passion hits so hard that your hands are trembling, use every ounce of it. You can always sleep in an extra hour or two the next day.

Don’t trivialize what you do.

One of the biggest struggles we initially faced at Outspoken was really understanding what each of us brought to the table and bleeding that. [Okay, maybe it was just me and Rhea who struggled with this.] The two of us were both new to this whole thing and there was a bit of doubt in ourselves and, to be fair, sometimes each other. Even now, I can recall some of the early conversations Rhea and I shared and it makes me wince. Insecurity is contagious and it spreads like a disease. When you don’t believe in yourself and what you bring, you cause others to question it. You open the door to being micromanaged. You walk softer than you should. And there was a lot of that the first month of Outspoken. And then it stopped. And when it did, we became more efficient, more productive and started kicking 200x more ass.

There is no time in startup life to be insecure about your talent or whatever anyone else brings to the table. You need to understand it from the very beginning and then bleed it out of every pore. If you’re always questioning yourself and putting off your responsibilities due to fear, then you’re sabotaging the company and you should get out now. That first month of Outspoken sucked at times, but we’ve conquered it and we’re better for it.

How to spell ‘entrepreneur’.

Yeah. That was a tough one. It deserves a mention.

Ignore people who try to offer you a job.

I’m offered a “real job” at least once a week. The offers come from very well-intentioned folks who want to help and offer me a position with benefits and a salary and real coworkers. They want me to know I have options, you know, should I want to jump. And it’s all very sweet of them. Except for the fact that I have a job. It’s running Outspoken Media, building a brand, and managing the content, communities and voices of our very awesome clients. So, no, while I much appreciate your job offers, I already have one. Thanks for thinking of me.

Don’t let people’s need to keep offering you stability make you question your own.  You’re good.

Create your virtual water cooler.

I may have a job, but it’s sometimes an isolating one. I work alone out of my apartment for 10-14 hours a day where the only things I have to talk to are Jack and Swat. As cute as they are, cats suck for conversation. They also don’t appreciate my totally funny jokes. I think somewhere along the line I was supposed to make “non work friends”, but…shut up, I never did.

Because I don’t have a physical office, I’ve created a virtual one. Skype has become an essential work tool for me. It allows me to pop my head over the cubicle whenever I need it. If I have a question, need advice, or just have a funny story to share, my fellow “coworkers” are there to listen. We’ve created our own mini network, complete with Friday happy hour. I’ve also built a schedule for myself where I’m working outside of my apartment in wifi-enriched coffee houses a lot more. Getting out of my apartment tricks me into thinking I’m really “coworking” with all the other people sitting around me. It also means I get to talk to new people and gives me a reason to shower and change my clothes on a daily basis. These are all nice things.

I don’t know what it is, but getting out of the house and working where life is happening and where people are excited…it helps. Use it.

Actually, I don’t have a job.

I take back that previous one. This isn’t a job. It’s simply a lifestyle that I have chosen for myself because I am part ambitious, part masochistic. And the sooner you accept that about yourself, the more content you’re going to be living it. You may even like it.

Commiserate with other entrepreneurs.

Sometimes when you work alone and you’re putting in crazy hours, you feel like you’re crazy. You forget why you’re doing this. Why you love this. What the goal is. And the only way to overcome that is to surround yourself with people who are equally crazy and obsessive about their work. Because you’ll find your reason in their passion and their excitement. Oftentimes, this means hanging out with other entrepreneurs because, frankly, they may be the only other people who will really understand.

I’m not saying entrepreneurs are “better” or “strong” or “smarter” than people with 9 to 5s, I’m saying that when I met Mike Germano last week, I could see in his eyes that he understood exactly what I was feeling. When we sat down to chat after Social Media Breakfast and I started rambling and venting and being oh-so-happy for human contact, I knew he was right there with me. He gets the struggles. He knows the fear we all pretend we don’t have. By being able to share war stories, to complain, and to commiserate with people who get what you’re feeling because they’re going through the SAME THING…it’s invaluable. And then you remember that you’re not crazy. You’re actually incredibly blessed. And you get back to work.

Praise is to be feared.

The SEO community has been amazingly welcoming and supportive of Outspoken Media. Truly. The support that we received out of the gate, and the support that we continue to receive, is overwhelming. And we’ve tried really hard to be worthy of that support. At the same time, each time you tell me something positive, I’m half ignoring you. I’m sorry for that.

If I think I’m doing a good job, then I’m not motivated to do better. If I think this is “good enough”, then I start going to bed before midnight. I become content. I don’t ever want to feel content in my work again, because I’ve been there, and that’s when I’ve let jobs get boring. When I’ve let them become routine. Ignoring praise and telling myself I need to work twice as hard for your love is what motivates me. It means I’m always clawing my way up. I’m always growing. Outspoken is growing. And Outspoken means the world to me.

If you can accept praise without losing your fight, you’re ahead of me. Ignoring it helps keep me motivated, so that’s what I try to do.

Six months probably feels like a relatively short time to be in business, and I agree, it is. But I think the lessons you learn in your first six months of entrepreneurship are things to be treasured. Because you learned them the hard way. And you earned those war wounds. And frankly, most of you didn’t think we’d survive this long. ;)

I’ve love to hear some of your greatest work and life lessons.  Please share. I may die in Canada.

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