Creating a Pivot Point and Faith-Leaping

Success Principles from my first go at a Non-Profit, Grantwriting, and Failing

In the last year, since telling myself that I was going to build my businesses and create opportunities to work for myself, I’ve grown a lot – personally, professionally, entrepreneurially, and even spiritually. I want you to be a part of the new journey – side-streaming into full entrepreneurship. But, behind that is a simple three steps to me being more bold.

How often do you take a leap of faith? I write that as though doing it were easy. I admit, I let fear dictate a lot of my decisions for a long time, and never took a GIANT leap of faith.

Then I had a revelation.

What if you could practice taking leaps of faith, so when you take bigger leaps, it wasn’t so scary? Well, if the Coach in me didn’t understand that practice makes perfect, who would?

So, for the last year, I’ve applied a three-step approach to the goals that I have, even small ones:

  1. Push past my initial self-created limit (The BREAK)
  2. Set up an if-then risk assessment (The FEAR)
  3. Place the decision outside of your direct control (The LEAP)

The concept behind this approach works like this:

First, by breaking through your initial limit, you’ll effectively start to see how most of the barriers that are in front of you are self-created. More often than not, we tell ourselves what we can and can’t do, and what we are and aren’t capable of. Creating habits of breaking past your own limit is a foundation for success, a topic we’ll talk more in length about.

Second, recognition of your worst and most vain fears is a crucial step to actual progress. Recognizing what we fear the most, and often times for me it’s been totally silly, is the first step towards making a dent in them.

Finally, it’s not often that we are comfortable letting someone else influence our lives, but that’s why we do small pivot points over and over – so that the repetition makes it easy and less scary.

See the common thread here: Repetition.

Think Kobe Bryant – he’s a master because he does the fundamentals 2000 times per day, not because he was born a master of the jumper.


  1. Push past your initial self-created limit.

Last week I went through Hell Week, hosted by Ramit Sethi and Mark Divine, a Navy Seal Commander. It was about setting tougher goals, crushing your own limits and recognizing the mindset that creates success. One of the things we had to do was blow through our physical barriers by recognizing that we had never set a high goal and had the methods to get to them. For example, one goal was to complete a 21-minute plank.

My reaction: “I like weird physical challenges, and I’m in good shape, but there’s no way I can do that.”

Response from Mark: “How do you know? Have you ever tried?”

I failed even at my own psychology on this one.

It’s such a simple principle, but pushing past the limit we made for ourselves is incredibly powerful. When you do it once you learn a little more about how to set goals and how to get to them.

In college we did some crazy planks for maybe 3 minutes, but all of those were nothing compared to this challenge. I ended up completing the 21-minute plank by focusing on 30 seconds at a time. Even if I had failed, fallen, and collapsed at 6, or 10, or 15 minutes, I still would have CRUSHED the limit that I thought I had – This is exactly what we want.

I thought of a million reasons why I couldn’t be successful at my own business and my passions. Eventually, I decided that was bullshit.

This year, I decided, with a partner, to take on financial literacy education. I’ve wanted to teach in a less fundamental way for a long time, so there were a lot of self-obstacles in my way. The goal was to create a non-profit, a 501 (c) 3 business, then get into schools where we could make impact. Instead of a head on approach, we established a partnership to build with a school, that way we had a better idea of their needs, and could tailor to them. This would better ensure a ‘product’ that would sell, not to say that would make it easy.

We set a really, really tough goal. I didn’t even know with certainty we could do it….that I could do it. We wanted to have a product (educational programming) for launch in the spring. We wanted to develop a Pilot program, and $5000 would be enough for us to do a tremendous amount of hours with the kids, so we applied for a grant. While we worked on writing the grant proposal, we worked 20-40 hours a week on developing the product, the brand, and everything we could. We didn’t think we’d have enough to write about, or wouldn’t have the data or the costs, but like Parkinson’s Law tell us, we completed the task in the time we set forth for it. We submitted the grant, hopeful we could teach financial literacy to Baltimore youth, 2 hours before the cutoff. I never thought we would. We broke our limit.

The BREAK taught me a lot. I’d never written grant, never started a non-profit, and never built an educational product. But, like the first time I had sex, I was nervous and anxious and, of course, eager. In the case of sex, even at 18 (late bloomer, here) I knew the outcome was worth facing the fear, but for something like this, there’s not a pretty woman on the other side telling me how awesome it would be. Now I know, it’s totally worth breaking through the limit, and feels just as good.


  1. Set up and if-then risk assessment

Applying for the grant and planning to launch a Pilot in the spring wasn’t easy. It took some balls to request money for something we didn’t have yet. Working from 5pm-11pm a few nights a week, we probably went through 564 K-cups, 29 gallons of creamer, and 16 lbs of organic grass fed butter. The Keurig recently bit the dust, too. L

When we sat and submitted the application, we had a drawing board out (my windows), and started a two column chart to track what would happen if we got a yes versus a no. We were playing chess with failure and success, so that we were two steps ahead – even a failure didn’t render us forfeited.

If we got the grant, we’d need to have the product ready. We’d still have to go to the school and get approval to launch. We’d need minimal supplies, but with some capital, we’d make it work. Our biggest crunch – if we got the grant, we’d need to find staff. That was our challenge. We sat and analyzed how we could find staff, bring them in, and what it would cost to do so. Planning for success was soccer 101 and we were at halftime – tied 0-0.

We planned for failure, too. If we didn’t get the grant, we had to either use our own money to fund the project, ask the schools to pay for it (which we didn’t want to do), or find another grant. We would have to reposition, reach out to other companies and see if they were willing to fund the pilot. We set down a firm but delicate objective if the grant didn’t come through. We would not give up, we would continue to work on honing our product, and we would try to get in front of more people to showcase our after-school program.

When we really analyzed the worst case scenario, we wouldn’t have lost much, but working so hard in case we heard a yes was going to give us a lot of progress.

The conversation where we really analyzed our FEAR, the absolute worst case scenario, was priceless. We didn’t have to close shop, didn’t have the earth collapse, and didn’t lose any credibility. When we figured that out, we knew it was the right decision to press forward and stop worrying.


  1. Put the decision outside of your direct control

Submitting the grant was a small “out of our control” decision in the big picture, right? But we still had to overcome something big within ourselves. We couldn’t really go any farther without funding, and though we continued to hone the product and the audience, we still needed to get money. Which comes first, money or the product???

We leapt hard.

No product ready, just hope, a goal, and some grit.

When we sat down the next day, you should have seen the realization that we had on our faces. Shit. We have to have a product ready in 30 days. Good thing there are services like Amazon Prime for coffee.

By taking that small leap of faith with the grant, and knowing we had a month to go before our intentional launch, we started taking more action. That meant shaking more hands, talking with more schools, and asking for help and support. We had experienced the first taste of faith-leaping. The benefit – propulsion from the expectation we put forth of ourselves. It was a cool drug. Motivated to deliver a happy handshake to that check writer was going to be a good feeling.

We poured in hours to the product, the curriculum, and the system. It was moving so quick. We we’re going to finish this in time. On the day before we got the word, we stayed up late, printed our flyers and materials, and had everything ready for the school. It was exciting to see and feel the work we’d done in our hands.

The email came the next morning and we got on the phone before we opened it.

We didn’t get the grant.

A wave hit us. Failure. Loss. Depression.

Then another wave hit us. We had already taken 3 other leaps into other funding options, school relationships, and partnering opportunities. Momentum was compounding. We prepared for this, just stick to the plan.

The LEAP taught me that when I put a decision in someone else’s hands, it motivated me to be a better representative of their decision. If I got picked to run a program, I wanted to make them look good. If I get picked to speak at a conference, I want to kill it, and if I client picks me for his project or as a consultant, I want to bring massive value.

But, until I placed that decision elsewhere I was stuck – with all that control comes little motivation to break out of the comfort zone.

Training the faith-leaping skill is like anything, you have to do it before you can say you’ve done it, and one comes before two. Before I knew it, I was approaching these leaps more and more – creating sustainable relationships, taking on mentors, longer lasting business deals, and more solidified goals.

When I really looked at it closer, what did I have to lose anyway?

Since you might be wondering, we still haven’t found the grant that will pay for everything, but we did manage to squeak a small grant out of someone that we did contact through our outreach in our middle step. It netted well ultimately, because it’s a partnership that could grow.

Now, as I go to embark on even bigger leaps of faith, I remember that if I push myself to the limit, and I’m prepared and ready with some risk-assessment (at least as best as possible), then the rest will come. That’s not to say I won’t fail, but business and personal growth doesn’t come from not failing, it’s from finding a way to keep moving and keep going after the failure.

There’s beauty in taking leaps of faith, and I intend to take them from here on out. At the end of the day – what the heck is there? No risk, no reward, and certainly no fun.

First, we BREAK our limit.

Then, we face our FEAR.

Last, we LEAP.

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