Today, as I look at my “day job” and my freelance writing practice as my main revenue sources, my web publishing projects (my own hobbies) make up the third leg on my career stool. They actually support the other two by broadening my horizons, but still keeping me within the scope of the things I like to do and can accomplish without a lot of cash invested. If I drop a few bucks here or there on server fees or software upgrades, it’s okay, since it’s my hobby and I don’t have to wait for it to produce ROI right away. And if it doesn’t, it’s not like I put everything on the line. Not going to do that again.

So, from the point of view of a new hobbypreneur, what’s “at stake?”

Certainly, you’re not investing any more in a hobbybiz than you would on any other kind of recreation. Spending $9 on a domain name is cheaper than a movie ticket. Spending $10,000 to design a web site means this better be more than a hobby.

By my definition, any income from your hobbybiz should be something you’re delighted to enjoy and something that you can still live comfortably without.

By their estimates, about 50,000 full-time sellers earn enough income to replace a typical salary (or more). The other 1.25 million earn significantly more than most of the auction site’s users, which makes me wonder if they’re hobbypreneurs. Full time eBay sellers have figured out how to drop ship or acquire overstock inventory that they can still sell at a markup. Hobbypreneurs on eBay tend to be artisans, craftmakers, and entrepreneurs who have figured out how to build a solid reputation in a niche.

On the flip side, it’s getting tough to be a full time travel agent unless you specialize in something really remarkable in your market. Cruise specialists still do well, as do bucket shops and travel consolidators. But very few folks are asking travel agencies to handle routine Memorial Day or Thanksgiving plane reservations.

Thus, a huge opportunity for hobbypreneurs. Registered travel agents enjoy perks like discounted room nights and standby airline travel. A growing number of part-time travel experts have popped up online, offering added value through guided tours, recommended trips, and special group rates. While becoming a full-time travel agent might not be as lucrative a deal as it was three decades ago, part-timers looking for perks instead of income can turn their hobby into profit.

Be careful, however, if you shop online for travel agent certifications. Some unscrupulous vendors offer travel agent opportunities that turn out to be little more than Ponzi schemes tied to a specific reservation system. Travel agents, travel writers, and tour guides who operate respectable practices are often happy to share information about joining their ranks without getting ripped off.

1. Eliminate opportunities for disaster and double-booking.
Moving into a job where I had to be “clocked in” from 9-5 meant setting some strong boundaries for clients. One of my businesses, a teleclass recording service, required me to make commitments to be available at odd hours throughout the week. When I was totally freelance, this was a great business, since I could often do it while doing other things. When I merged my business with another web marketing company, we had resources to help handle many of those calls. But moving out of that environment meant saying goodbye to that income stream. I no longer had to worry about clients who might be disappointed that I couldn’t block out a certain time for them, and I found ways to earn more income by focusing my efforts on single tasks during my freelance time chunks. I realized that many of the biggest service problems I encountered stemmed from making too many commitments in that area. Letting go really freed me up to focus on things I really enjoyed doing without the potential for urgency.

2. Set communication boundaries in advance.
One freelance IT professional with whom I collaborate frequently has a “day job,” too. It keeps him busy from 8am-3pm, so he can take on client projects from 4-10pm. Clients that get testy about not being able to reach him before 4pm don’t make his cut — he tells them up front that they’re not going to be a fit. He also advises new clients to contact him by e-mail instead of by phone, since he can respond more quickly to messages at the start of his second shift. While I understand the fear that some freelancers have about divulging their “other lives,” preparing the client in advance is far less risky than cleaning up after a communications meltdown.

3. Open up self-serve options.
Another thing that successful hobbypreneurs do, as evidenced in The Four-Hour Workweek: put as much of your business on auto-pilot as possible. After handling fulfillment for my own products for seven years, I let a third-party distributor do all the heavy lifting. While I was afraid I’d lose too much profit margin and control by handing over the reins, the result was less urgency in my life and the ability to refer our mutual customers to a dedicated customer service team. Allowing automated scheduling and confirmations also makes clients and customers feel like they’re being taken care of, even if you’re on the other side of town plugging away at your day gig.

4. Post clear communication channels.
When a customer of your hobbypreneur enterprise really does need something from you, make it clear how you can be contacted and what your turnaround time will be. On an outbound voicemail message, advise callers when you will get back to them. I often use the phrase, “the close of the next business day.” I follow that up by posting my personal work schedule on the private intranet I use with freelance clients. This way, they know what my “office hours” are and when I can get back to them. Using a separate business number from GrandCentral or uReach can help, as well — this way, you can avoid giving out your cell phone number and allow only notifications of incoming calls.

5. Arrange discreet notifications.
Along the same lines, message filters and voicemail settings can allow just the most serious situations to get your attention while at your day job. I use filters in GMail and .Mac to allow only the most urgent messages to ping me on my iPhone. I can excuse myself for a break and handle an emergency request from a client. (Usually, that request is to confirm my availability for a last minute project instead of a total meltdown — it’s why I sold off my web hosting business years ago.)

This list is far from complete, and I’ll probably revise it a lot over the coming months. But these are all strategies that keep me sane and my clients happy.

This week, I finally got to sit down and absorb Marci’s book, which really distills the trend in our world right now: we no longer expect a single job or a single employer to provide every piece of the fulfillment we seek in our lives. We often speak of work/life balance. However, there’s still — for some of us — the need to have a work/work balance, or the desire to stretch every one of our creative muscles and still get paid for it.

As I see it, hobbypreneurs are a distinct subset of the “slash” professionals that Marci writes about. The profile theater director/computer programmer comes to mind, as do many passages about lawyers who act, sing, and dance. The most important thing to take away from this book is the kinship with folks like the author herself, a lawyer/journalist, who have spent so much of their time justifying their actions to friends and family. There are so many of us who seek creative fulfillment alongside financial reward, understanding that it’s not always fair or accurate to expect a single job to hold all of that promise.

From his own experience, Tim suggests that a really efficient entrepreneur can operate a profitable business in about four hours a week. In most cases, that requires taking an existing business and pruning down to the most important activities. For startups, this philosophy involves letting go of preconceived notions about more hours = more money. Tim emphasizes making smart investments of time and resources instead of merely slogging away with brute force.

Therefore, I looked at ways to trim the hedges on my side projects. Certainly, my paid freelance writing is still a “job” instead of a “hobby,” but I still had to get more efficient in that part of my life. The biggest area of opportunities came from my skunk-works projects, like standalone websites and side blogs.

My biggest takeaway from Tim’s book was to evaluate the ROI for each of the projects I’m involved in. Under my definition of being a hobbypreneur, something’s got to be a lot of fun for me to spend time on it if it’s not earning me as much money as my job or my paid writing projects. I let go of a lot of domains for projects I wanted to start, but hadn’t found the time for. Like sloughing off dead skin, the projects that meant the most to me came bubbling up to the surface.

I must admit that I tried using one of the virtual assistance agencies Tim listed, and didn’t have much success. The folks at the overseas agency were very helpful and exceedingly polite. However, when I tried to have them confirm appointments and make research calls for me, the folks on the other end of the line found them difficult to understand. (One vendor called me up right after a confirmation call and asked me if I was playing a prank on them.) Still, should I ever get back to the point where I need lots of help making calls, I won’t hesitate to use a domestic VA service.

Echoing the earlier work on Thomas Leonard, Farriss emphasizes eliminating the routines and tasks that don’t immediately get you closer to your goal. In my case, I’m not trying to pare my work life down to a total of four hours per week so I can go on travel adventures like Tim. Instead, I’m trying to balance a job I love with a personal life and with the projects that can earn me significant amounts of income from just a small investment each week.

Once I started writing about the music business on a regular basis, I dusted off spinme.com again and used it primarily to promote my books. From 2003 to about 2006, that site was the hub for the bulk of my income. So I backed into what Darren Rowse calls problogging. The success of spinme.com led to my coaching other entrepreneurs, many of whom used blogs to establish themselves as experts in their fields.

But, when I wound up taking a corporate gig in 2007, spinme.com withered again. I had less time to work on it. And, frankly, less passion. Probloggers are very good at pounding out new content every day to stay on top of search engine results. If you’re not motivated by ad dollars or incidental revenue, your writing style changes. You focus on longer pieces that update less frequently.

That’s a big shift for a hobbypreneur. With money coming from elsewhere, blogging can be a profitable hobby. You don’t have to grind it out to earn three dollars a day in AdSense revenue. But it’s nice to know that a simple post you wrote three years ago generates enough passive revenue to pay for your web hosting and still treat you to a latte (or, in my case, a hot chocolate) everyday.

Without the pressure to be an expert, you can go on a journey with your audience and still end up generating some revenue to make your time more productive than if you had been playing video games or chatting all day. That’s where I see blogs fitting the hobbypreneur lifestyle — great content being created by folks who don’t necessarily depend on it for the revenue.

But it’s nice to know that a simple post you wrote three years ago generates enough passive revenue to pay for your web hosting and still treat you to a latte (or, in my case, a hot chocolate) everyday. Without the pressure to be an expert, you can go on a journey with your audience and still end up generating some revenue to make your time more productive than if you had been playing video games or chatting all day.

A hobbypreneur is someone who has a “day job” that they actually enjoy, but also loves working in a creative field that just happens to earn them extra money. Some people spend their free time hunting, fishing, or playing Wii. Other people start rock bands, write books, launch blogs, or sell crafts on Etsy.

Creative career professionals spend 100% of their time developing products and performances for their audiences. “Starving artists” that work at day jobs they don’t like might reduce that down to 50%, with the friction of spending half their energy on a career they’re trying to get rid of while they spend the other half trying to get discovered.

Here’s how I joined the ranks of the hobbypreneurs, and learned to love it.

In 2001, I left my full-time job as a radio producer to start writing and consulting. I wrote four books about the music industry and traveled the country to promote them. I earned as much as $150 an hour, consulting with musicians who needed help with marketing proposals.

And then, my wife got sick. Our small business health insurance carrier decided that her undetected genetic defect was, by their definition, a “pre-existing condition.” I had to shut down my consulting practice and find a job that would allow me to afford health care. Ultimately, I wound up at a company that I never thought I would work for, doing I job that I found I had a true passion for. I backed myself into a new career, a great paycheck, and a surprising love for what I was doing.

Yet, I still had this drive to keep writing, creating, and exploring. With the luxury that I didn’t need to make money doing it. After all, my books were still selling at a decent clip, and my websites were generating advertising revenue. So I refocused my attention on doing just the things that I wanted to do. Sure, some of my audience weren’t too happy about it, and they have gone on to get their needs met elsewhere. That’s what’s so freeing about being a hobbypreneur. When your creativity becomes a secondary income stream, you don’t have to worry so much about pleasing every single member of your audience.

I had run into this behavior before, when I consulted with musicians.

There’s one musician in particular who started the hobbypreneur idea bubbling inside me. He was the head of a growing company, but loved playing live music. The entrepreneur in him refused to believe that he would just do that for free, so he got focused on marketing his music just as aggressively as he would market his business. Yet, at the point where many musicians would quit their day jobs and hit the road, he dialed back. And he never complained – all he focused on was a core audience in his home city. Since he got all the validation he needed from small, packed houses, he didn’t need to risk everything else just to try to “make it” as a musician. After all, he was perfectly content with all aspects of his life.

And that’s a trend that is relatively new for Americans. We define ourselves so much by what we do, that it’s so hard to envision ourselves as more than one thing. At some companies, doing more than one thing is considered a horrible thing. Where I was working in 2001, I was flat out told not to do anything else creative – even on my own time – since it meant that I wasn’t giving my all to my job. And I am sure that there are probably places where folks are still getting that kind of treatment.

Still, more of the musicians, writers, and artists I meet through my current work share my own interests: punching in to a fun job, then punching out to do something creative, and earning revenue from both pursuits. Having been a part of the music industry for almost two decades, I can confidently say that some of the very best songs and albums over the next ten years will come from hobbypreneurs – folks who are so secure in their primary income stream that they can create fantastic art, free from corporate interference and free from the commercial demands of finding audiences that support them.

During my vacation in 2008, I read One Person / Multiple Careers, by Marci Alboher. She chronicles lots of folks who like to do more than one thing in their lives, and a lot of those folks are doing more than one thing at once. In a job market where creative mashups are critical to success, employers understand the benefits of hiring hobbypreneurs. Like my wife’s friend who is a barista and a fine artist – so the menu board at her shop always looks nice. Or my colleague who is a trained neurosurgeon and academic writer, who works in a retail store to keep from being bored during lulls between drafts. (And isn’t that what I told myself I was doing when I started there?)

I don’t think this is a contradiction to what I wrote about in Grow Your Band’s Audience. In fact, it’s complementary. If many bands are capable of sustaining strong revenue from 1,000 true fans, why not set that as a goal while developing other sources of income?

In my case, my income streams evolved over the past few years until I didn’t have to worry so much about getting my personal projects to pay for themselves. Two of my books came directly from my audience’s demands to write on particular subject areas. But I don’t know that I had the same passion for them as I had for my first two books. (Not that they’re bad or anything. They just felt more like something I was expected to do rather than something I felt I had a burning desire for.)

Right now, this topic is where my burning desire is. In the same way I felt such a connection ten years ago to struggling musicians, I now feel a kinship to other hobbypreneurs who want to spread their creativity without it turning into a second full-time job.

Will it become a book?

Probably. And yet, I’m in no hurry to make that happen, since any income I generate from that will be a nice “multiple streams” thing for me, anyway. What you can expect here are columns that take what I’ve been writing for other sites even deeper – folks who aren’t just changing careers, they’re defining new job strategies by doing what they love.