How I Decide What Business To Start

Recently I asked my readers to tell me what they wanted to hear more about, and the thing I got asked the most was to tell more about how I do things. How do I run my businesses?

Well, as you are probably aware, I am a huge believer in context. So first, I want to show you how I choose my businesses.


Now, in the first place, the idea of choosing a business might seem foreign. If the internet forums I’ve read are any indication, the biggest problem that would-be business owners have is trying to figure out what skills they have that someone will pay them for. Either that, or they know what they want to do, and they then are trying to figure out how to get paid for it. Then they quickly segue into figuring out how to position their offer, how to reach potential clients, and so on.

I certainly started that way. But never let it be said that I don’t learn from my mistakes. These days I’m very choosy when I start a business.

How much do I like what I’m doing? Do I like it too much to make a business out of it?

My first-ish business was selling hand-painted figurines. This was not in any way a sustainable business, but that didn’t matter, because before very long, it wasn’t the act of painting itself that was important to me. What became paramount was having inventory that I could sell. Under the pressure to produce, it sucked the fun out of it and lowered my quality.

I also decided not to pursue novel writing as a career for similar reasons. I was pretty sure that having to write, whether I wanted to or not, would suck the fun out of it. Ironically, I seem to have come full circle, but it’s a lot easier to write non-fiction than fiction. Don’t let anyone tell you otherwise.

This happens to me every time I get a hobby, to the point where I have to consciously talk myself out of selling the fruit of my leisure time. I realize that this is not a common view, what with all the people telling you to find work doing your passion, but keep in mind, those aren’t passions of mine. They’re just leisure activities. And doing them for pay skews my motivations. Maybe it doesn’t work like that for everyone, but it does for me.

Is this challenging and fun? Am I learning a lot? How long do I think my interest will last?

Back when I used to try to get jobs, I took it as a given that I would be looking for a new career every year or two. I’m a scanner, I can’t help it. As soon as the learning curve levels off, I’m bored out of my gourd.

After a while, it just became easier to start my own business than it did to convince employers to take a chance on me. I tried doing ATV rentals for surveyor companies (that went nowhere, but I did learn the importance of market research.) I did small retail sales. I did the trade show circuit for a year, selling on commission. I was certified as a Reiki practitioner. I did market research surveys by phone (I was a contractor, so technically it was my own business). I started a handyman company with my then-husband and a B&B with my mom because I just loved building businesses.


A lot of the people I work with go into business because of a passion for what they do. I start businesses because I love to create something from nothing. Did you notice something about my list? I never duplicated industries.

What would happen is I would notice, or be made aware of, a niche that had an untapped market. Then, I would try to figure out some way to serve that need. A micro-business is often able to thrive in niches that isn’t worth the while of a larger business.

But, I would always get bored, as soon as the business was up and running smoothly. The day-to-day work, the actual, technical work of running a business doesn’t excite me. Why do you think I started systematizing things? So that I had to spend as little time as possible doing that stuff, and outsource it if possible.

Now to Get Stringent

For the first ten years or so, I was an amateur. Given my scanner tendencies, I knew I had to get businesses that could be profitable quickly, because I knew I wouldn’t be in it for the long haul. But I didn’t have an exit strategy for any of these businesses. When I got bored with them, I just quit doing them. After a decade of working my tail off, I had virtually nothing to show for it. Everything that I had done, I never wanted to do again.

I had learned one thing: I was freaking sick of businesses that relied on the weather or the whims of people with disposable income. There were too many variables I couldn’t control for, and I don’t like to gamble.

So about that time, we finally got internet in my area. No, this wasn’t that long ago (’09 or ’10) but I was just living really far out in the boonies. I had heard that people could really make a lot of money online, but I was kind of fuzzy on the details. (Yes– up until this point all my businesses had been off-line. I didn’t even have a mailing list.)

So, I began to research it. I am, quite frankly, amazing at research. You kind of have to be to learn as many industries and skills as I have. I realized that most people who made money online had computer skills– programmers and designers. Or, if they didn’t have computer skills, they had sales skills– those were the internet marketer types. But there was a third category of people… coaches.

As far as I could tell, all you had to do was give advice. Good advice, certainly, but advice nevertheless. If you helped people, well, the proof was in the pudding. But proof was hard to come by. I could tell that this wasn’t going to be a business that was quick to take off.

So I started a blog, and I hung out my shingle as a “Life Transition Coach,” figuring that if I was expert at anything in my life, it was change. Mostly, my clients were divorced women, but they were few and far between, so I was still helping my mom run the B&B.

(Funny aside: I started collecting email addresses from people who visited or expressed an interest in the B&B, but I still hadn’t heard of Aweber by that point. I practiced my internet marketing skills by emailing every B&B promotion individually, by hand. Yes. I knew mass mailing was bad, but I didn’t know there was an alternative.)

A coach with no clients spends a lot of time “networking” on Twitter (or at least, we did in those days. There’s probably a hipper place to hang out now. (Also, don’t you love that I’m talking about 2010 as “those days” like they’re the distant past?)) and I joined a couple of forums. It was there that I learned that I Had Opinions on how other people should be running their businesses.

Now, here was the next brainwave. Not only was giving business advice a lot more fun that just generic ole life advice, it was less prone to be classed a “luxury” which meant that selling people on the idea was a lot easier. I always prefer to sell something people need. So I refreshed my offerings to teach people how to run their businesses more effectively.

But, because I knew I wanted to focus on mundane, unsexy stuff like processes and systems, even this revampment was going to be slow going as well. It’s kind of like selling socks and underwear. Everyone needs them, but nobody really talks about it like they do shoes or jeans or purses.

In 2010, we had a massive flood, and the B&B was destroyed. We had insurance, but it would have taken us several years to rebuild, which wasn’t just starting at zero, it was starting at -10, because the beautiful gardens that people also came for were just as wrecked and we would lose all the marketing momentum we had gotten while we rebuilt. So I told my mom to take the insurance payout and leave it be.

I was at loose ends, and I knew my wee little coaching business would not be paying the bills anytime soon. So I was on the lookout for another business, one that I wouldn’t hate, wouldn’t require me to practice customer service, and one that preferably took place indoors.

A friend of mine told me about selling used books on Amazon. His parents suggested it, as they had had some success selling off their collections and were looking to branch out. I did some research and thought to myself, this could be something. The trick would be to find enough books worth reselling. So, I decided to give it six months.

The $10,000 investment broke even in less than 3 months.

You might have to have experience in retail to realize how staggering that result is. 3 months. For the first time in my life I started to feel like a real entrepreneur (and remember, I’d been running businesses for more than a decade at that point. 10 years before I stopped feeling like I was faking it.)

Okay! This internet stuff is pretty cool.

The book business was just about ideal. It takes about 4-8 days a month to run it, depending on how many book sales we attend. The only problem? It’s seasonal. It’s really busy during Q4, and it’s got another spurt of activity during April and May.

That left me a little at loose ends during parts of the year. Given the choice between aggressively scaling Change Catalyst or finding something else to do, I started looking for other sideline business options.

(Another aside: I know it doesn’t sound like it, but I really like seasonal businesses because it doesn’t give me enough time to get bored doing one thing. Plus, it’s a little bit of a challenge coordinating the overlap. I know that this isn’t an attractive prospect for many, so I don’t advise it, per se, but personally, I enjoy it a lot.)

About this time, I was learning SEO to use in promoting Change Catalyst. The more I learned about SEO, the more it seemed that high quality, native English-speaking writers would be needed desperately as Google overhauled its algorithms. What a coincidence! I was a high-quality native English-speaking writer!

I knew at the outset that I would get bored quickly (writing is not typically something that remains challenging to me for long) but I also realized that this was the kind of business that you could easily outsource. Writing all day, every day, wouldn’t be my cup of tea. But owning a business where a staff of writers wrote all day, every day, providing me with an income? That’s the stuff that capitalist wet-dreams 4 Hour Workweeks are made of. Besides, I’d been wanting to try the E-myth style of building out a business for years, and I’d just never had one that would scale in quite the right way. So that was going to be my next challenge.

Except– then Change Catalyst started to grow. The book business started to grow. The SEO writing business took off like a shot, through a couple of lucky flukes. (Don’t ever underestimate how much flukes contribute to your success. The book business itself got off to a promising start when we started it on accident at the beginning of the holiday buying season.) And at the moment, all three are operating as a throttle-choke on each other, because I have no more time to give them. Figuring out where to spend my time for maximum short- and long-term effect remains my largest challenge.

What Have I Learned From All These Businesses?

However much fun it is to build a business, you have nothing to show for it until you can hang in there for 3-5 years. So most of my decisions in creating a business come down to honestly assessing myself and deciding if I can maintain my interest that long. Seasonal businesses tend to work the best for me because I can intersperse activities that are more lucrative or that are more interesting in there.

I discovered I can also build a business if I am passionate about my offering. That would be business coaching, natch. While my other businesses were simply economic opportunities, Change Catalyst actually makes me experience feelings.

When I think about my Right People and what they’re struggling with, I get a little choked up. It’s hard. I’ve been there. Even though I had the best possible launching pad, it’s still hard, and scary, and just flat out awful at times. But it’s also so amazing in other ways that you can’t quite bring yourself to give it up.

So although my primary passion is building businesses on my own, it comes as a surprise to me to realize that I don’t anticipate getting tired of coaching. I am fiercely determined to help my tribe find the support, the encouragement, and the information I so desperately wished for in my own early days.

Are you one of my Right People?

Since I’m on the topic (and since you’ve stuck with me this far) I want to mention that if you are one of my Right People, you may want to join my private community, The Guild. It is free, and I hope that it will support you in your business endeavors. Because it is private, though, you have to click this link and request to join. This is to keep out the internet marketing types, and keep the community tight-knit and high-quality.

If you want a community of like-minded people with whom to bounce ideas and share insights, please join us.


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