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The bootstrapper creates value

The times are nothing remotely like that any of us would have predicted just a few months ago. And many of the institutions and jobs we depended on have changed, perhaps for a long time to come. It’s going to be a slog.

And as always, there will be the other side of the slog.

Where will the solutions be found? How do each of us choose to contribute?

Into this void, it’s possible to show up with something new, something you start, something that solves a problem.

One of the most powerful things you can do is build a useful business. An enterprise of value, doing work of substance, filling a need and finding independence.

And to do it without raising money from a bank or waiting in line for a venture capitalist to smile at you is where freedom can be found.

You’re not a bootstrapper because you are thinking small. You’re a bootstrapper because it offers a chance to chart your own course and to serve your customers without conflict.

Innovation almost always comes from individuals who see a chance to make things better. Instead of waiting, they go first.

We’re relaunching The Bootstrapper’s Workshop today. We are connecting entrepreneurs seeking to make a difference, and doing it in a proven format that opens doors and helps you think even bigger. Something that matters for the long haul, not just a week or a month. Follow the link and look for the purple circle to save some money on enrollment. It’s at maximum value today.

I hope you can join us.

Don’t know (can’t know)

If your career depends on detection and selection, it’s a helpful fiction to imagine that you’re doing something more than random guessing.

College admissions.

Greenlighting a movie.

Picking stocks.

Publishing a book.

The data makes it clear, though: while it’s possible to be worse than average at most of these selection tasks, it’s almost impossible to do consistently better than the average.

As William Goldman said, nobody knows anything.

It’s so much more honest (and efficient) for a selective college to send a letter to the people who meet basic criteria and say, “you’re good enough, but there aren’t enough slots, so we’re going to pick randomly.” Because the truth is that a randomly selected class of qualified people is going to be just as high achieving as any other combination they could create.

And if you’re the one who wasn’t picked, don’t sweat it. They don’t know better. They can’t.

Beware of experience asymmetry

There are things you’re going to do just once. Get your tonsils out. Pick a caterer for your wedding. Raise money from a venture capitalist. Apply to college.

In these situations, the institutions and professionals you’re dealing with have significantly more experience than you do. Not only that, but they know that you’ll be gone soon and they’ll still be around.

In these asymmetric situations, it’s unlikely that you’re going to outsmart the experienced folks who have seen it all before. It’s unlikely that you’ll outlast them either.

When you have to walk into one of these events, it pays to hire a local guide. Someone who knows as much as the other folks do, but who works for you instead.

Students come and go, but deans last for generations.

On predicting the future

Two things:

We do it all the time. Constantly.

We’re terrible at it.

We spend our days guessing how an action will impact the future, and we’re often wrong.

And we spend the rest of our days hoping we were right or worried that we weren’t. We try to control the future by telekinesis and anxiety in equal measure.

When the future doesn’t cooperate, we spend even more time trying to change the next bit of future so that it ends up more closely matching the future we were hoping for.

What if, instead, just for a little while, we simply did our best?

And let the future take care of itself.

Because even if we don’t fret, the future is still going to take care of itself.

All that’s on us is to do our best work. Paying attention to models and the community and the people we serve.

The message and the messenger

If your job is giving people good news, it doesn’t necessarily mean you’re doing a good job.

And the opposite is also true.

Often, we conflate the situation with the people involved, but that’s a trap. Our job isn’t to make people happy, it’s to create the promised change with care and professionalism.

Going to the dentist hurts less if you have a dentist who cares about you and the process.

All models are wrong, some models are useful

That’s what makes it a model. The map is not the territory, and a model is nothing but a stripped-down approximation of what might be happening. By definition, the model for your problem, your organization, your opportunity–it’s not actually the thing being studied, it’s a simplified version of it.

At higher magnification, your model is wrong. It has to be in order for it to be a model.

And yet we need models.

We need a model because if the elegant, pure, refined model doesn’t work, it’s harder to understand why your messy, real-world situation is going to work.

Not all logical and structurally sound models turn into successes in the real world, but better to begin with something that makes sense.

What do you make?

It’s possible that your job is to make decisions.

If that’s what you do, what would it mean to do it more productively? With less hassle or drama?

If we make decisions all day, how can we do it better? Because that’s the question every other professional asks about her work.

If we make decisions for a living, it might be worth figuring out what would happen if we made better ones.

Toward better

There’s rarely a straight line from here to better.

But there’s usually an arc.

The slog won’t last forever.

And winning streaks aren’t endless either.

As we move through time, we’re often presented with opportunities that are carefully disguised as problems. And every day we’re forced to make a choice. The default might be to hold back, but it’s not the only option.

The chance to move toward better can become a habit.


[It’s time to find the others, others on a journey like yours, who want to do things the right way. Coming soon, an antidote for the entrepreneur who feels isolated. The Bootstrapper’s Workshop is coming back. Sign up on the site for updates and a discount code. We’re doing it again because it works.]

“But we were comfortable”

Some of the shift to digital is unwanted, fraught with risk and lonely.

But in some areas, organizations and leaders are realizing that it’s actually more powerful and efficient.

So why didn’t you do it before?

Because it’s easier to follow.

Because it’s more comfortable to stay where we are.

Waiting to do something because you’re forced to is rarely a positive approach to growth or leadership. Abrupt shifts against our will may cause change, but they’re inefficient and destabilizing.

Next time, take the lead. Not because you have to, but because you can.

You’re surrounded

We all are.

Throughout a lifetime, everyone has their troubles–someone might have stubbed a toe, or missed a car payment or be studying for an upcoming exam. Big problems and small. We each have our fear, our grief, our hassle.

The thing is, the troubles were local and unique. It was easy to walk away from our drama, at least for a moment, because someone else, everyone else, had something else they were dealing with.

For the last month, that hasn’t been true. For anyone.

You can’t avoid it, can’t walk away from it and have to work to put it in perspective, because every interaction comes with someone else amplifying the story.


At the same time the echo chamber around us magnifies our story, we also have the solace of knowing that truly, it’s us.

Us together.

The boat is really, really big and we’re all in it.

This is a slog, and there will be another side. It is unevenly distributed, it’s a tragedy and it’s a challenge. But we’re in it together and with care and generosity, we can find perspective, possibility and hope.