It takes a certain amount of confidence to be a founder. Some would even call it arrogance.

The audacity to believe that you have a better idea. To believe that starting your own thing, on your own or even as a bigger company, is the best way to bring that better idea into the world.

I had that idea for me. I called it Creating Extraordinary Futures™.

But the Creating Extraordinary Futures that I created in 2017 and what exists today are incredibly different.

Because I also needed humility. The humility to change, to pivot, to adjust.

To see who my ideas resonated with and who they clearly did not. To see how I could make my ideas easier to understand for those who were interested. To continue to adapt the Creating Extraordinary Futures Process™ as my thinking changed and as more clarity emerged.

I see this with my clients, too.

They might start with arrogance, but if they think they have it all figured out, they will likely fail.

People want a road map. So much so that they will blindly follow those who claim to have one.

There is no map. There is no predefined path. What worked for entrepreneur extraordinaire will not work for you. Because you are a different person. You need to find your own way, as I found mine.

You say you want clarity, but the only clarity I know of is the clarity of knowing what to do next. Of taking the very next step.

If you are looking for that kind of clarity, let’s talk.

One of the reasons that I love coaching is actually quite selfish.

I am in a constant search for truth. I have been my whole life. It is why I went to law school. It is one of the things that led me to meditation and working with spiritual teachers. To getting a coach and then becoming one.

Socrates had it right when he focused on learning through dialogue. Because there are things that come up in conversation that I have not seen come up in any other way.

I already know what’s in my head. I hear it over and over again. But to expose myself to what is in another human being’s head, and soul?

That is when the insights come. Sometimes those insights are for the client, but often they are for me.

Even when I am talking to a camera, there is a person in that camera lens who I am in conversation with. I am guided toward what that person might need from me. Through some mysterious process, I am teaching and learning from a person I may not have even met yet.

I don’t pretend to understand this process. But I do honor it. And I know that there is nothing more powerful to learn new things about myself, and the world.

What have you seen through conversation that you have not seen before?

A founder once told me that most new businesses don’t actually fail. Instead, the founder simply runs out of time, or money, or enthusiasm.

Giving yourself enough of all of those is critical to maximizing your chances of success. But persistence still plays an incredibly important role.

At every step of my own journey, choice points arose as to whether and how to continue the business, when to bring on other people, when to scale.

These are not easy choices and I’m never quite sure I’ve made the correct ones (or even that there is a correct choice).

But there are a few questions that I have learned to ask myself along the way. Even now, seven years into my coaching business, the answers to these questions still help be decide where to focus and what to say no to.

1. Do you still enjoy the process?

Do you enjoy doing what you need to do every day to build the business? For example, I have had other coaches ask me about my “social media strategy,” and I really don’t have one. Instead, I create both written and video content that reflects as accurately as it can what I currently believe AND what I have observed works for my clients. I enjoy the internal process of uncovering that truth and trust that the right people will resonate with what I have created.

2. Given what you have learned, does your goal still seem possible to you?

You must continue to believe that the goal, whatever that is, remains possible for you. Even inevitable. Every day you must act as it achieving your goal is inevitable. And if you cannot, it might be a sign that it is time to move on.

3. Do you still want what’s on other side?

Occasionally, I discover that I don’t really like working with a particular type of client or a particular type of organization. There used to be a side of me that thought that, for the sake of the business, or the money, I still needed to take on that work. I have learned, though, that focusing on the work that I truly want to do, with leaders that inspire me, is worth so much more than the money I might make doing something I am not as inspired by. And generally, the increased focus means that my business ends up growing, not declining.

4. Do you have the resources to keep going?

If you don’t have the time or money to continue, can you get them? If the idea is still promising, and the belief is still there, you must find the resources, or the regret will be unbearable.

What are the questions that have helped you know when to keep going, and when to stop?

There are two ways to do anything.

You can do it as a way to get to know yourself at a deeper level.

Or you can do it as a way to escape from that, even as you tell yourself that you are doing the opposite.

When I was starting my coaching business, I starting having coaching conversations before I got my official certification. I found I learned more from those conversations than I did from the training (even though the training was incredibly helpful).

Yet I had many classmates who, years later, were still not coaching, thinking they needed more training. Just one more area of expertise, just one more certification, and then they would be ready.

I have seen people go on spiritual retreats to AVOID looking more deeply at themselves, to create themselves as victims of their circumstances, their trauma, rather than actors in continuing to accept their lives or choosing to create themselves differently. They go on another retreat rather than integrate the most recent one into their lives.

I have business owner clients who hide at work so they don’t have to look at dysfunctional relationships at home. Saying “I have to work,” which is in fact the exact opposite of what is happening for them.

I find a helpful question for me is “What am I choosing to avoid right now?”

In writing this post, I was avoiding working on my taxes. I was avoiding reaching out to potential clients.

I might also do work to avoid exercise, or exercise to avoid work.

Am I running toward challenges or away from them? Am I increasing my capacity for discomfort or decreasing it?

There are no easy answers to these questions, but even to ask them is to move toward doing the necessary work.

What are you running toward, and what are you running away from?

And when do you simply need a break?