In my recent review of Pam Slim's Escape from Cubicle Nation, Chett left the following comment:

I was talking with a good friend last week who is self-employed. I told him I envied his entrepreneurial spirit and the ability to “go it alone.” He told me he envied my work as a teacher and the set hours and guaranteed pay check and insurance. (I told him there was nothing “set” about the hours, so I guess we both misunderstood each others work.)

So many people dream of working for themselves and only find out the true benefits and heartaches after they make the leap. Take you for instance, what do you miss the most from the box factory in terms of security, or interaction? What bothered, (or motivated) you the most to drive you to self-employment and what have you learned about your decision over the past year and a half?

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More about...Career, Side Hustles

Last Friday, I attended a workshop put on by Pamela Slim, who writes about entrepreneurship at Escape from Cubicle Nation. Before this meeting, I didn't know much about Slim or her message, but her work came highly recommended from my friend, Chris Guillebeau. "Pam is the real deal," he told me. "Her book is what a lot other books have tried to be."

Based on this recommendation, I drove to hear Slim speak. I was impressed. Chris is right: She's the real deal. I was so impressed, in fact, that I spent the weekend reading her book, which is also called Escape from Cubicle Nation.

Opening Up to Opportunities

Escape from Cubicle Nation starts at the beginning of the entrepreneurial journey: deciding what to do with your life. Slim spends several chapters discussing how to get in touch with what's important to you. At times, this almost seems touchy-feely. Almost.

"You don't have to be world-class great to make a great living doing what you love," Jonathan Fields writes in Career Renegade, "if you are willing to step outside the box, approach your passion differently, find innovative ways to mine that passion for money, and work like crazy to make it happen."

In Career Renegade, Fields draws upon his own experience, as well as that of others, to provide a blueprint for those willing to take that entrepreneurial leap of faith.

Career Renegade is an odd book. Its title and marketing might lead you to believe it's about careers. As I write this, it's the number one book in Amazon's "job hunting" category, which is baffling. Career Renegade isn't about job hunting or changing careers. It's about taking your passion and turning it into a business. It's about entrepreneurship. As long as you expect this going in, it's a great book.

Last month, Alison from Diamond-Cut Life shared an article about providing lodging to a housemate in exchange for work (instead of rent). Her story prompted a number of readers to ask about the mechanics and practicalities of actually renting an extra room to generate income. For example, Penny wrote with the following:

In August, my brother-in-law moved in with us. By December, he couldn't find a job, so moved back out. While I had mixed emotions about his leaving, I did lament losing the potential income, because I thought my husband would never agree to renting a room to a stranger. Imagine my surprise when I mentioned the idea and he agreed to it.

I need some advice as to some things we should consider when finding a renter.

If you want to start a business, the best $20 you'll ever spend is to find successful entrepreneurs and take them out to lunch. They can be from your industry or other industries — it doesn't matter. For example, if you're interested in hospitality, you could pick up a hospitality magazine and see who's doing interesting work. Then email them and ask to take them out to lunch.

Spend 90% of the time talking about them:

• Ask them how they did it.
• Ask them what mistakes they made along the way.
• In the final few minutes, you can ask about your idea. Is it crazy? What should you be thinking about?

After you meet two or three people, you'll start to see patterns that you hadn't recognized before. And that's when you realize how powerful it can be to ask others for advice. Continue reading...

I spent a couple hours this morning performing what ought to have been a simple home maintenance task. The light fixture on our front porch had gone faulty, and I needed to replace it. I've done enough wiring projects now that the electrical aspect of the job didn't bother me. But the woodworking? That was frustrating.

As I fumbled with the jigsaw ("Drat! Another blade bent!"), I wished again that I practiced woodworking more often. I have several friends who do so, and the skills they've learned help them to save money around the house. My incompetence this morning gave me plenty of time to reflect on the value of productive hobbies.

Productive hobbies

When I was younger, I spent most of my spare time reading comic books and playing video games. There's nothing wrong with a little self-indulgence, but the older I get, the more I appreciate hobbies that provide practical skills. Productive pastimes are not only fulfilling, but they can also help save money. (Sometimes they can even generate a little income!)

A couple weeks ago, J.D. had a conversation with some friends about starting a small business. I liked a lot of what was said, but I've had some different experiences, and would like to offer my perspective. Here are some things I've learned from my entrepreneurial endeavors.

Starting a business with friends can be fantastic
Both of the companies I've co-founded have been with long-time friends, and while of course there were hard parts about it, in many ways it was a huge help.  We knew each other well enough to figure out how the other would react in a lot of situations, and had a base level of trust that is always helpful.  Of course there are plenty of counterexamples, but it can work.

What matters is that you have a partner with whom you can communicate — if that person is a friend, great.

My friend Nicole and her family visited our house for breakfast this morning. She and her husband are the founders of Green Ronin, a Seattle-based game publisher. As we enjoyed a couple lovely hours outside at the picnic table, we chatted about life and work. We talked about what it's like to own a small business.

Because my father was a serial entrepreneur, I've spent most of my life around small businesses. Chris and Nicole have had a taste of the lifestyle over the past eight years. They've seen the bright spots and the dark, and have some strong opinions about entrepreneurship.

"What sort of advice do you have for somebody who might be starting a small business?" I asked. Here are the highlights of our conversation:

Working Away From Work

I got my start as an entrepreneur completely by accident. You can read the whole story here, but the short version is that back in 1999, I needed to make some money. The bills were due, my third-shift job wasn't going so well, and one day I took some photos of random stuff around my apartment and put it up on eBay. I made about $22 an hour right away, so I quit the night job and started building a wholesale business.

I've had a lot of different small businesses since those early days, including website design, publishing, and Google Adwords consulting. I've also had some crazy experiences along the way, and made a lot of mistakes.

Despite the mistakes and occasional uncertainly of not having a regular paycheck, my ten years of being out of the traditional workplace have made me a passionate believer in working for myself. I don't have a large business — I work at home, and I don't employ anyone directly. I have no plans to do that in the future either, because I'm comfortable with the super-small business model I call microbusiness. Continue reading...

Last weekend I explored Portland's beautiful Eastmoreland neighborhood during its annual 140-family garage sale. In the past, I've come away with major bargains, but this year I had to be content with enjoying the first day of summer with a couple of friends. We admired the homes, gardens, and assorted cast-offs of the well-to-do.

Many of the adult garage-salers were raising funds for charities. Sidewalks and curbs were also strewn with young entrepreneurs selling their wares: homemade cookies (still warm from the oven), beaded jewelry, rice-krispie treats, iced bottled water, and grilled hotdogs.

Over the past two years, J.D. and I have had fun meeting one pair of entrepreneurial sisters who rise above the run-of-the-mill baked goods and soda. I was pleased to see them once again. In 2006 they were selling jokes: