Change Catalyst with Shanna Mann: Strategy & Support for Sane Self-Employment

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Discernment. It’s a big value of mine. To discern what is useful, what is important, what’s germane. To know how far to go — or at least to have the sense to retrace my steps when it’s evident that I’ve gone too far.

Discernment is a tricky thing to teach. It’s even trickier to give advice on. But I strongly believe that discernment (a fancy term for wisdom and good judgment) is really the key to a successful life. Because so often, when mistakes are made, they are not mistakes of kind, but of degree.

This is hard to demonstrate in business (so full of variables and so impossible to duplicate or set up controls.)

But, let’s take a look at another realm…

Too Much of a Good Thing… obviously stops being good at some point.

My husband was telling me about a book he’s reading. The author laments the way that specialization has reduced us to automations, and pegs the change at the Industrial Revolution.

I see his point. But at the same time specialization is what raises humanity above subsistence living. To be forced to grow your own food, grind your own flour, weave your cloth, do your own metalsmithing, cut your own timber, and so on — was, and is, impossible. (Yet another reason why I’m so cynical about the near-universal cultural yearning to ‘return to the simple life.’)

The problem is degree. Some specialization is beneficial, even revolutionary. Taken too far, it destroys many of the things we find desirable.

Even during the Industrial Revolution, factory jobs, while dangerous and perhaps tedious, were highly in demand, because it released people from farm labour and at least allowed them to see something of the world. Plus, you might have only been a pin maker or a tanner, but it was still considered a trade; and a trade meant status over a common laborer.

In fact, it wasn’t until Henry Ford really popularized the idea of one guy doing nothing but sinking one bolt, an hour after an hour, that people really got reduced to automations.

Men like Frederick Taylor, seeking to optimize every shovelful of coal, took the concept and ran with it, and sure, now you can make the argument that many jobs reduce human labour to nothing more than a mechanical process, devoid of creativity or judgment on the part of the worker.

Moreover, such specialization requires no mastery — it has been specifically designed to be un-fuck-up-able — and in doing so it has completely disenfranchised to the person doing the work.

The problem is degree. Some specialization is beneficial, even revolutionary. Taken too far, it destroys many of the things we find desirable.

Another common problem of degree is weight loss. There is nothing wrong with changing up your diet to kick off weight loss, even though it isn’t strictly necessary. The novelty of a new diet can help you think critically about things you do unconsciously. But when people hop from diet to diet, compulsively, either chasing a miracle cure or chasing the results they get from those first few weeks of novelty, what we have is a potentially useful idea stretched far past its useful boundaries.

And as a final example: an old joke/parable that I expect you’ve heard before.

A vacationing American businessman standing on the pier of a quaint coastal fishing village in southern Mexico watched as a small boat with just one young Mexican fisherman pulled into the dock.

Inside the small boat were several large yellowfin tuna. Enjoying the warmth of the early afternoon sun, the American complimented the Mexican on the quality of his fish.

“How long did it take you to catch them?” the American casually asked.

“Oh, a few hours,” the Mexican fisherman replied.

“Why don’t you stay out longer and catch more fish?” the American businessman then asked.
The Mexican warmly replied, “With this I have more than enough to meet my family’s needs.”
The businessman then became serious. “But what do you do with the rest of your time?”

Responding with a smile, the Mexican fisherman answered, “I sleep late, play with my children, watch ball games, and take a siesta with my wife. Sometimes in the evenings I take a stroll into the village to see my friends, play the guitar, sing a few songs…”

The American businessman impatiently interrupted, “Look, I have an MBA from Harvard, and I can help you to be more profitable. You can start by fishing several hours longer every day. You can then sell the extra fish you catch. With the extra money, you can buy a bigger boat. With the additional income that larger boat will bring, before long you can buy a second boat, then a third one, and so on, until you have an entire fleet of fishing boats.”

Proud of his own sharp thinking, he excitedly elaborated a grand scheme which could bring even bigger profits, “Then, instead of selling your catch to a middleman you’ll be able to sell your fish directly to the processor, or even open your own cannery. Eventually, you could control the product, processing and distribution. You could leave this tiny coastal village and move to Mexico City, or possibly even Los Angeles or New York City, where you could even further expand your enterprise.”

Having never thought of such things, the Mexican fisherman asked, “But how long will all this take?”

After a rapid mental calculation, the Harvard MBA pronounced, “Probably about 15-20 years, maybe less if you work really hard.”
“And then what, señor?” asked the fisherman.
“Why, that’s the best part!” answered the businessman with a laugh. “When the time is right, you would sell your company stock to the public and become very rich. You would make millions.”
“Millions? Really? What would I do with it all?” asked the young fisherman in disbelief.

The businessman boasted, “Then you could happily retire with all the money you’ve made. You could move to a quaint coastal fishing village where you could sleep late, play with your grandchildren, watch ball games, and take a siesta with your wife. You could stroll to the village in the evenings where you could play the guitar and sing with your friends all you want.”

The American was proposing growth. Growth for growth’s sake is a pretty dominant cultural theme. But to what end? Eventually the American said — family, relaxation, the good things in life. And the Mexican, well, he thought he was already there. And since he was there, he was not about to give them up.

I find that bonsai business owners understand this intuitively, but they also want a little bit more than the Mexican fisherman — usually, security in the form of money in the bank, or a house, or the financial breathing room to travel. If they have kids, paying for education is also a concern.

Since you’re reading this on the Internet, it is highly likely that your culture teaches you to equate business success with achieving all the finer things in life. But it’s really only loosely correlated. Like a Venn diagram, if you will. And with a bonsai business, you have a considerable level of control — exactly how big you get, and also, the luxury of easily scaling back down if you find that a certain size is not what you wanted.

The thing is, no one wants to scale back — it involves saying ‘no’ a lot, and it tends to feel tantamount to throwing away security, which it is not.

How To Prune Your Bonsai Business

When you prune a tree, you have to think both in terms of getting rid of what’s unnecessary, and in preparing for what you do want.

Cut the Deadwood

So, the first thing you do is cut out all the dead, broken, or diseased branches.  That’s pretty easy, and most people do this with their bonsai businesses as a matter of course. Except, when the diseased branches take up a large proportion of the business. Then, they get scared.

In the gardening world, this is what’s known as a “hard prune,” and it IS scary. It can kill the tree. But, what you have to realize is that the tree would have died anyway. It was diseased. But if it doesn’t kill it, it makes it much stronger, because suddenly all the effort that was put into trying to heal that disease is now put into new, fruitful growth. This new growth might not be quite as aesthetically pleasing for a while (because it tends to enthusiastically splay in all directions) but soon enough you’ll be able to see it take shape.

If you have to cut out a lot of diseased wood, then just do that, and wait to see what new growth develops. Too much pruning at one time will be counter-productive.

Lop the Branches That are Going in the Wrong Direction

This is a hard stage for beginning pruners too! Because we’re going to take otherwise health branches that are not what we want, and chop them off.

There are two ways that this can be done. The first is the easiest.

Branches that will cross with other branches. In nature, when this happens, they rub up against each other and cause damage. In your business, this looks like a business avenue or income stream that works at cross purposes for what you want. For instance, if I value the freedom to have a lot of days free of meetings, I’m much better off pruning aspects of my business model that require me to have a lot of meetings!

The second kind of healthy pruning is harder, because you’re making a judgment call.

Branches that are going at the wrong angle. I have this cherry tree with most of its branches roughly horizontal. But some of them are going off at a 45 degree angle! I’m going to prune those, not because they interfere with the other branches, but because they are not what I want the tree to look like. I am banking on a new branch to appear with the proper look, or that the others will fill in the gaps and the odd branch won’t be missed.

This move is VERY controversial in businesses, mainly because it’s tough to share an aesthetic vision.

I know of a woman who was making very good money giving talks. It wasn’t that she hated the work, or the travel, or that she wasn’t getting paid enough or that it interfered with other things she wanted to do. But it just wasn’t the vision she had for herself, and so she pruned it.

If you can’t imagine yourself ever getting to the stage where you’d prune a healthy branch off your business because it didn’t exactly match your vision, that’s fine. Just understand that it’s an option.

Pruning is more of an art than a science, and that’s why discernment is crucial to it. And like pruning, remember that every year you get an opportunity to prune a little more, so it doesn’t have to be done all at once (and probably shouldn’t!)

Remember the art of knowing how far to go. When you get a little too small or the branches too sparse, give them time to grow in again. When you see everything get overgrown and messy, get out your little snippers. Most of your problems will be a matter of degree, not of kind. So the easiest thing to do is just to back off a little and let a natural balance reassert itself. 


It’s interesting to me that sometimes the issues that my clients have sort of clump together. It’s a bit surreal when you have the same issue three calls in a row.

Right now several people are dealing with the “What Got You Here Won’t Get You There” problem — so named after the book by Marshall Goldsmith.

Goldsmith is an executive coach who takes the high achievers who are now at the peak or nearing the peak of their careers, and helps them to not shoot themselves in the foot by using behaviours and frameworks that worked while they were on the upward climb, but not so much once they got there.

Think you’re too far from your goals for this to be affecting you? Maybe not.

One client, a serial entrepreneur like me, keeps talking about keeping his options open, even though he’s got a business that is going well. But this business will require a significant amount of focus to build into a stable and secure operation.

For so long he was trying a bunch of different things to see what would work and he’s still mentally in the habit of scanning the horizon for the best opportunity. He needs to remember that he’s already picked a business that is doing more than showing promise, it’s on the cusp of succeeding, and to focus on that.

Another client is a born connector. And it’s brought her a lot of opportunities. Too many, in fact. She’s swamped under not just the work that these connections have brought in, but the opportunities for events, trips, dinner dates and Meetups.

She knows she should say no — she knows she is HAS to say no. But she also knows that every connection is an opportunity. And she isn’t mentally “there” in her current success to realize that a) she has more opportunity than she can handle, and b) she can go out and create more opportunity anytime she has the notion.

She’s still in the mindset of “showing up”and “hustling” but she has to evolve to a stage of pruning and curating in order to do her best work.

And lastly, a common one I’ve seen many times: you’re growing your list, your followers. For a while you know your whole tribe. You probably friended a bunch of them on Facebook, so you see their whole lives, too. But as you grow, you start feeling like me you don’t know these people. And they don’t seem to know you. They just want something from you, whether it’s your time, your art, or for you to entertain them. You feel resentful, taken advantage of, and like you lost your tribe somewhere along the way.

This is normal too. You went from “being a person” to being a brand, or in some cases, a product. The connection you forged with your early adopters was useful and rewarding in its time, but ultimately unsustainable. You cannot support that many relationships.

In this new stage, you need to do two things; one, build a connection with your tribe another way, and two, figure out how to adjust your emotional mindset so that the new normal no longer seems so awful to you.

Put yourself in the shoes of someone a little bigger than you, in your niche. Probably they have cool friends, and an inner circle of amazing clients or beta testers/readers with whom they insulate themselves from the wider world that sees them as a brand, as an object of utility to be deserted when no longer entertaining or relevant.

Awareness is 80% of the cure for these types of mindset problems.

These shifting stages catch most people off guard. It doesn’t occur to them that what worked well for them in the past might not work as well in the future. But when it’s pointed out to you, you recognize the ridiculousness of that assumption. The very absurdity seems to give the realization an emotional impact that makes it stick.

However, we are still all creatures of habit, especially when it comes to strategies that historically have been successful for us. So it’s worth asking yourself every once in a while, “what’s not working for me anymore?” It’s frustrating to have to pick up new strategies, but not as frustrating as scuttling your own business because you couldn’t change your mindset when you needed to.



Over 18 million people have “Liked” the Humans of New York page on Facebook. I’ve been following it for several years, and I’ve used many of his stories as examples of unlikely perspectives.

If you’ve never heard of this page, it’s actually a cool story. This guy, Brandon, found himself unemployed. So to keep himself busy, he started wandering the streets of New York, taking pictures of some of the people.

Eventually, he started asking them questions. And that’s where the real meat is. To see a stranger — really see them — and hear a snippet of their life story: it humanizes the Other and connects us all. His pages so popular that he’s been asked to travel, and humanize other Others. He just finished a project on Syrian refugees, and before that, the global tour of Muslim countries.

But for my money, the best stories have come from the children with cancer.

Brandon was invited to visit the Memorial Sloan Kettering Cancer Center.

It’s so personal, the way each family friends their fight. It’s also different because each cancer is different. Sloan Kettering treats some of the rarest cancers in the world.

So some kids come in with what amounts to a death sentence from something untreatable. Others have a more hopeful prognosis.

Some have put all of their trust in the treatment advice. Others have fought hard, getting second, third, and fourth opinions, until they finally found a doctor who said, “maybe there’s something we can try…” It really depends on the individual details of the situation. Of course, every family is desperate, but even in a cancer ward, there are degrees of desperation.

One girl, Gracie was one whose family fought a dire prognosis. She had been treated the usual way, but it had no effect. The doctors started talking about how to “keep her comfortable.” The mom wouldn’t take no for an answer. She’d gone to all kinds of doctors and they all told her, “There’s nothing we can do.” Until at Sloan Kettering, they suggested an experimental treatment that triggers the immune system to attack the cancer cells.

Gracie has this sort of rosary she calls her Courage Beads. Apparently the treatment centre staff give you a bead for different events, for each chemo treatment, for each needlestick. She even has two heart-shaped – she got them for two separate episodes when her heart stopped beating.

Something I love is the way she calls them Courage Beads, and not the more mellifluous Bravery Beads. This is because in my personal dictionary, bravery and courage are two slightly different concepts. I must have read this distinction somewhere, so firmly is it set in my mind.

Everyone knows you can be scared, and still be brave. The essence is in not running away. But in my view, bravery is when you stand and fight. Courage is when you run towards the threat. Bravery is defensive. Courage is offensive.

In Gracie’s situation, bravery would have been to take the first five opinions, to fight the good fight. To hope for the next round to perform a miracle. It’s grim, but there’s certainly virtue in this path, to stand and fight even when there’s so little hope.

Courage, on the other hand, can be seen as foolhardy. As reckless. Experimental treatments? Make your child a guinea pig?

And Gracie’s mom didn’t listen.

Maybe she regretted it, at times. She tells Brandon, “It was so painful. It felt like she was getting a root canal over her entire body. After two rounds of treatment they did another scan. They wanted to see if there was any progress. The therapy was so painful that if it wasn’t working they wanted to stop.” Imagine sitting next to your child while they undergo the excruciating treatment that you fought for, but couldn’t know if it would work.

She was irrational, you might say. She decided the odds didn’t apply to Gracie. But since Gracie’s cancer would have almost certainly killed her anyway, her family decided to take the risk. They strode towards the danger. High risk, yes. But high reward.

And she lived. After two rounds of the experimental treatment, all the cancer was gone.

As a Bonsai Business Owner, I want to see yourself in these families.

Not with cancer, God forbid. But in the way that you express courage and bravery.

You have a business. Ask anyone what the odds of success in business are. They’ll happily tell you. 1 in 5. Probably worse! Yet here you are anyway, brick by brick, bead by bead, trying to build a future in your own terms.

Is it irrational? Foolhardy? Maybe so. But the prognosis for those with ordinary jobs and ordinary careers is not so good, either. So we’ve decided to step forward, closer to the danger.

For some, the upside of the straight job is so small that it’s self-employment or bust — that’s certainly the case for me.

For some, it’s more like an insurance policy. The job is stable and pays the bills for now, but there’s a chance that it will all go down the tube, and when that happens, they’ll be ready.

But there’s also no point in judging the people on the original path. The families who accepted the first treatment plan, if you will. Because every situation is different. Every set of variables. And statistics are meaningless at the level of the individual.

So that’s what I have for you this week. Sorry to be so bleak. But as we all know, building a business is lonely, in part because courage looks so foolhardy. You’ll never persuade someone who doesn’t understand the choices you make. And hopefully now you can see why.