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One year ago today (Nov 1) I made the leap and started my own business. Here’s what I’ve learned.

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November 1, 2011

I’m publishing this on November 1, 2012, exactly one year to the day that I was laid off from my full time gig at Conde Nast and Wired. I thought it would be a great time to give my fans an update and share some of the tips that I learned so far.

First off, I want to start by declaring that I am renewing my contract for another year.

What do I mean by that?

When I lost my job, a lot of people quickly offered help at finding something new, passed along openings, or wanted to meet with me. When I told them I wasn’t planning on getting a new full time gig, the next question was asking me how long I was giving myself to succeed, which also might be viewed as “when do you think your money will run out.”

While I never really set a hard deadline, I figured I would definitely give it a run for a year and see what happened at that point. Well, while I might not be back up to the full time salary with benefits and 401(k) that I was at, there’s no question that I am going to keep going down this path. Put it this way, I haven’t updated my resume yet.

Here’s another great sign. I just got the traffic stats, and October 2012 was the highest number of unique visitors this year and highest number of page views in the 4 1/2 year history of The Hopkinson Report. So thank you.

Here are 5 things that I learned as an entrepreneur in year 1:

1) Procrastination is your enemy


This is by far the biggest problem that I’ve struggled with in year one. I consider myself an extremely hard worker, and without a doubt, I can get in a groove and work very intensely. In fact, I’m almost always on the clock, doing at least some work during nights and weekends.

However, there’s also a huge issue with putting off the most important things until later. With no boss looking over your shoulder, it’s up to you to set – and adhere to – self-imposed deadlines.

What to do about it: I am working with my business coach to set specific goals in stone, and having her help hold me responsible for it. You can also use mentors, friends, or any trick that works for you to set goals and reach them. Today.

2) Overwhelm is the devil

This is one of the items every freelancer guide warns you about, and it’s true. The very nature of an entrepreneur is someone with incredible passion and drive for ideas, but this often leads to too many ideas and not concentrating enough on one of them.

It is especially relevant for me, as I have dipped my toes in writing, podcasting, teaching, speaking, conferences, and more.

What to do about it: I am giving myself permission to still pursue things I like, but am getting better at saying no to things outside my core goals, and doubling down on my major projects. Are you experiencing this as well? Let me know what is working for you (Twitter: @HopkinsonReport).

3) Where I work doesn’t matter


One thing some people said is that I would miss “the office dynamic,” going into an office every day and feeling a community of coworkers. I have to say, this hasn’t been a problem for me.

I’ve worked from home, from coffee shops, from co-working spaces, from friend’s houses, from bars, and even poolside in a foreign country on more than one occasion.

For the most part, I’ve had good discipline and haven’t missed the rows of cubicles. However, I have found that when I do leave my home for a coffee shop or co-working space, good things come back to me. Whether it’s coming home to some mail I was waiting for, or getting an email in regard to a new project, getting out of the house seems to pay dividends.

What to do about it: While I can’t yet justify paying $300-$500 a month for a co-working space when my home office has everything I need, I want to specifically carve out days to do so for another reason – I seem to meet really cool connections when I do. But every person is different, so do what works for you: on your couch in your pajamas or in a suit at a remote office.

4) Networking doesn’t end, it becomes more important


When I first left my job, I spent the first week or two purposely taking a break. I called it “network-a-palooza” and spent each day having coffee, lunch, and drinks with as many people in my network as I could. I wanted to tell my story, hear where they were in life, talk about what I planned to do, get advice from them, and see if I could help them. It was great.

I thought that the amount of networking would decrease or become less important as a freelancer, but in fact, it’s been quite the opposite. As a full time worker, you can sometimes let your networking slide a bit in between job searches. Not so with freelancing.

What to do about it: I recently thought about declining more meetings with both people in my network and new acquaintances out of it, but I know that’s not the right thing to do. So what I try to do is keep them to a manageable number, schedule them around coffee or lunch (hey, a man has to eat), and keep them to a reasonable length before going back to work. But I have to tell you, connections are vitally important. Don’t let this part of your business suffer.

5) The lifestyle rocks

Listen, is my business exactly where I want it to be right now? No. But I’m not beating myself up, as some people take years to get to where they want.

What I can say is that the year has been awesome in terms of lifestyle. Starting out with an international trip to Buenos Aires in January and continuing with another to Thailand in September was easily the highlight. But throughout the year, from conferences in March (SXSW) and July (WDS) to road trips to North Carolina in June, the one thing that can’t be beat is the lifestyle.

But it’s not just the big events, it’s all the little things day to day. Taking a break if you’re tired. Sleeping in if you don’t feel well. Taking a 3 hour lunch on a nice sunny day. Spending more time with friends and family.

What to do about it: Keep it up! I know I need to bear down and get some more things in place, but I also know this might not last forever. As my business goals and personal relationships change over time, I might not have this opportunity, so I’m taking advantage of it now for sure. What about you? Are you ready to make the leap? If not, when? What is holding you back?

Bottom line:

I’ve found that it’s been an incredible year, one of the best of my life. Yes, running your business is an enormous challenge. I’ve learned a lot about myself, and you’re truly hustling 24×7.

But the payoff in lifestyle and the fact that I am dedicating my work to helping others has been amazing. I hope I’ve been able to set an example that others can follow.

As they say, it’s about the journey, not the destination.

Thank you for being part of it, and look forward to a lot more in 2013.

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