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The Not Knowing Path of Being an Entrepreneur


Lots of people who start businesses try to control outcomes:

  1. A vision for your business’s success.
  2. Goals to get you to the successful vision.
  3. Try to get the most productive day (out of yourself, or employees).
  4. Try to produce certain amounts, or hit certain metrics (pageviews, followers, revenue, sales).

Unfortunately, the ability to control outcomes is an illusion. This is one of the fundamental lessons I’ve learned in my six years of being in business for myself.

You don’t really know how things will turn out.

And this is OK.

In fact, it’s pretty awesome.

Yes, not knowing how things will turn out — day to day, month to month, year to year — is crazy scary. I’m not gonna front. It’s so scary you might wake up drenched in sweat.

But not knowing is what makes being an entrepreneur more amazing than working a regular desk job with a regular paycheck. We take risks, we fail, we don’t know what’s going to happen, we not only put our toes into the waters of the unknown … we dive in, headfirst.

Yes, not knowing is scary. But if you embrace it, not knowing can be liberating, and can be an advantage.

Let’s look at how it’s an advantage, and how to stay present in the middle of the unknown.

The Advantage of Not Knowing

Quiz question: What causes us the most anxiety? Million dollar answer: Wanting things to turn out a certain way. Wanting an outcome — wanting the person you love to love you back, wanting people at your meeting or presentation to like you, wanting a million customers, wanting to be the next Apple or Twitter or Starbucks. This is the cause of our anxiety, because when we want that outcome, we fear that it won’t come true, and we strive for it to come true, and of course it might not.

There are a million possibilities, and wanting just one of those possibilities is a little crazy. What’s wrong with the other 999,999? Will our worlds fall apart if that one outcome doesn’t become a reality? No. We’ll be just fine no matter what.

Seriously. You’ll be absolutely fine even if the outcome doesn’t happen.

So when anxiety comes up, if we learn to let go of needing that outcome, we can then let go of the anxiety.

So advantage #1: we have less anxiety. What happens when you have less anxiety? Well, you’re happier. You are happier when you meet with customers or clients or employees. They feel your happiness. They sense that you’re cool with how things are going. You are less desperate. You don’t need things to turn out a certain way — you don’t need this one sale. You do your best to make it happen, but you’re cool even if it doesn’t.

Other people bet everything on making their outcome happen — but what if it doesn’t? Then they’ve lost everything, with no clear direction of where to go when it fails to happen.

So advantage #2: we aren’t as tied to one bet. That’s a single point of failure. Not a great idea. Instead, we are OK no matter what happens, and so any outcome of a meeting, a project, a launch … we are good with that, and no outcome really messes us up. We flow.

Another problem is that people who think they know how things will turn out … they’re fooling themselves. No one knows.

And that’s advantage #3: we are more honest. Admitting to ourselves that we don’t know is much more honest than thinking, hoping, things will turn out the way we want. Honesty is important because if we’re going to act, we should do so with open eyes and a clear assessment of the situation.

Honesty with customers, readers, clients, employees is important too. Admit you don’t know. They will trust you more, because not only are you telling them you don’t know, you are clearly OK with that. You don’t know what will happen, but whatever happens, you’ll deal with it. That’s powerful.

Those are just a few advantages, but actually the advantages are many. You don’t have to plan as much because not knowing means you realize that detailed plans are useless, and actually a waste of your time. You spend less time worrying, more time executing. You aren’t consumed by the horrible fear that you’re doing the wrong thing, because you learn that there is never a perfectly “right thing” to do — not generally for your business, or specifically right now.

How to Walk the Not Knowing Path

The Not Knowing Path of an entrepreneur is scary, but honestly, what path isn’t?

Here’s how to walk the path:

  1. Admit you don’t know. This is obviously the first step, but it’s hard because we often want to think we know, or at least that we can make certain things happen the way we want them to. We think we can will things to happen. That’s not true. Many things fail despite Herculean efforts to make them succeed. We don’t control the future, we can’t know the future. We don’t know. Admit it to ourselves, and to others.
  2. Watch for anxiety. When you start feeling anxious (and that will always happen, probably numerous times a day), look inward for the source of the anxiety. What are you hoping will happen that’s making you anxious? This awareness is the key to everything.
  3. Tell yourself you’ll be OK. You become aware of an outcome you’re hoping for … now tell yourself that it doesn’t matter if that outcome happens. It really doesn’t matter, even if we’ve made up this story for ourselves that all depends on it happening. It doesn’t matter, and no matter what happens, we’ll be OK. Life-and-death situations are possibly the only exception to this, though I’m of the mind that even death is an outcome that I’d be OK with.
  4. Consider worst-case scenarios. What’s the worst thing that could happen? Someone doesn’t like you, doesn’t think as highly of you as you’d like, a meeting ends in anger, a sale doesn’t happen, the business fails. How bad is this worst-case scenario? How likely is it to happen? How would you cope if it did? Honestly, I think you’d be fine no matter what.
  5. Know your principles. Take some time to think about what should guide you, if you aren’t guided by trying to make something specific happen. If you’re not tied to an outcome or vision of the future you can’t control, what would guide you? Step back, reflect. What drives you? Why do you do what you do? For example, some of my guiding principles are wanting to help others, wanting to act compassionately, wanting to do things I love, and building trust by doing those things.
  6. Act on principles, not goals or detailed plans. Once you have your guiding principles, let them guide you on a day-by-day basis, moment-to-moment. You don’t know how something will turn out when you act, but you do know whether this action is in line with your principles.
  7. Breathe, and smile. In the end, not knowing can be scary, but liberating and profound. You are in the midst of a turbulent sea, and are afloat without knowing where anything will go. But that’s always true, even of people who don’t admit it to themselves. So enjoy the ride. Look at the amazing place you’re in, and smile. Because this path of not knowing … it is the path of life itself.

‘If you realize that all things change, there is nothing you will try to hold on to. If you are not afraid of dying, there is nothing you cannot achieve.’ ~Lao Tzu


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