Those familiar with author Ryan Holiday are likely familiar with his book title and concept of “The Obstacle is the Way.” In short, it’s derived from the Stoic traditions that the impediment to action advances action, and what is standing in your way becomes the way.

Conceptually, it makes perfect sense.

When faced with an insurmountable obstacle in our path, we tend to change course or turn around. It dawns on me that Joseph Campbell’s “Hero’s Journey” also has elements that sync up to Holiday’s concept. In Campbell’s case, he outlines twelve steps in the Journey. The eighth step, “The Ordeal,” involves the greatest fear and most difficult challenge. The Ordeal is where the Hero comes face to face with the obstacle in their way. Get thru it, and reap the rewards. In both authors’ perspectives, there is no failure, only the option to get up and try again and again.

What is missing from both authors is a way to clarify The Obstacle or The Ordeal. It’s easy to look backward in life and connect the dots. To see the obstacles that were in the way that we’ve overcome. I find it significantly more challenging to look ahead and see the obstacles with clarity.

I have ideas on how we can find the most significant obstacles in our path.

At age 46, I thought I’d have it all figured out, whatever that means. If I’m truthful, there has been a strong self-narrative that I’m no different from when I was 24-years-old.

Obviously, this isn’t a factual statement. I’ve accomplished and experienced many aspects of life during that time; at a core level, I’m undoubtedly different. Why do I have this strong self-narrative telling me that I’m struggling with experiences that seem tied to my 24-year-old self? And why 24?

It’s tied to my inability to look directly at the obstacle ahead and accept what it says about me. My Ego fears the plain truth.

In 1999, I was about to graduate college, and I eagerly wanted to exit school and run my web development company, Unsoma, full-time. For the entire time I was in college, I tried running the business part-time, always struggling to find new business. That first year of running Unsoma, I couldn’t find new business. However, when I did get a lead, I could quickly close the business and service the client’s needs. I recall the first client I landed needing a technical solution to visualize their hardware. The innovative approach to creating the visual (pre-Flash) was a series of animated images simulating a 3D model. The work won me acknowledgment in Lydia Web, a well-known site for excellent web work.

I took this as validation and affirmation I knew what I was doing; business would be rolling in at any moment now. Except, it didn’t.

In my first year, that was my ONLY client. I had all the technological knowledge, the know-how, and a strong desire, but the clients never came. After one year of struggle, I was about to hang up the keyboard and surrender to rejoining the family construction business. That week I also sent my resume to a local web-dev shop that was more successful than mine; it was named Refinery. Luckily, they hired me, and I spent two years working for them before trying my hand again at my own business.

In 2002, I had my second chance by starting a new web development company named Imulus. This time I started it with two other business partners. Within months we were up and running, profitable nearly out of the gate. I took on the role of sales, sent cold emails, and smiled-n-dialed. Our first two clients paid all the bills, and with some black-hat SEO work, I was able to drive leads into the sales funnel continually. Life was good, and for ten years, we grew consistently, added employees, services, and expanded offices. Then the leads stopped.

My anxiety rushed back. The inner voice said, “shit, remember when you had Unsoma, you couldn’t find clients then; what makes you think you’ll find them now. Your fucked buddy.” I abdicated my sales role to a new employee. I neglected the responsibility and agreed to pay her whatever she wanted to take responsibility for new business leads. I believed I would fail to bring in more business. Nothing in my past suggested otherwise. My Ego was afraid, and it was easier to hide from my obstacle.

In her defense, she was able to close more business, but the costs of her sales commissions and salary cut deeply into our margins and hamstrung our ability to hire more talent. I sold my share of the agency in 2014; a year later, my ex-partners ran it into bankruptcy.

On my exit, I started a technology and marketing consulting practice, picking up the scraps from the demise of Imulus. Once again, I struggled to bring in new business. Thankfully a friend “saved me” when he needed a Sales & Marketing Director. At first, I was a part-time consultant, and I was excellent at executing the work. We doubled the leads in the first six months, and I took over the EOS Traction implementation project and received a bit of equity to join full-time, with the plan to prep for acquisition or capital investment.

A year later, we were acquired.

After six months of working with the acquiring company, I decided to venture off on my own again, back to the entrepreneurial world that I love so much.

But, the voice came back.

I’ve been at this coaching practice full-time for eight months now. The training has been good. The few clients I have are excellent, and it’s a win-win situation for all. Yet I’m only able to cover 50% of my bills. Now I don’t love sharing that, but the truth is the truth. 81% of coaches fail in their first three years. My experience over the last two decades has been rich, from running Imulus, President of the Colorado Chapter of the Entrepreneurs Organization, Techstar’s Alumni, TEDxBoulder Co-Founder to Director of Sales & Marketing. I’ve had plenty of experiences that apply to the clients I coach. Yet if I don’t address my obstacle, I’ll be part of the 81% metric.

Do you see my obstacle yet?

It starts with finding new business and making the initial connections with others looking for my services. It’s taken me over twenty-two years to acknowledge this fact. My Ego wouldn’t let me accept that new business is a challenge for me. If I don’t have web-based leads dropping into my inbox, I translate that to needing to find the work. My fear is deeper than rejection; my fear is being ignored.

I can take rejection. I can learn from “no.” But being ignored, what do I take from that? The internal narrative gets louder and says, “you aren’t valuable or interesting.” In short, it says, “you’re a loser; go home.” Ouch.

My obstacle is strengthing myself against the hurt of being ignored. I need to reaffirm that I have intrinsic value to offer. I need to shake off the feeling of getting ignored and continue to reach out. My Ego be damned! To not shrink to the challenge of being ignored. To quote Steve Martin, “to be so good they can’t ignore you.” That’s the obstacle that is in my way.

Now that I’ve shared my story, I believe there are a few questions that may help you find your obstacle. I plan to build this out into a workshop or worksheet to help others get clear on addressing their obstacles head-on.

1. What do you believe you aren’t good at, but if you were good at, life would be 10x better?
2. Where have you felt frustration throughout your life? When you arrive at an answer, ask yourself “5 Whys” to go deeper. When you arrive at an answer, ask, “why did you give that answer?” 
   For example, I’ve felt I’ve struggled more than necessary to be financially solid. 
   Why #1 — Because I can’t seem to find new business leads. 
   Why #2 — Because I’m not very good with outreach. 
   Why #3 — Because I’m afraid of getting ignored. 
   Why #4 — I tell myself I have no worth or value. 
   Why #5 — Inside, I need to start believing that I have value and a reason to exist.
3. What are potential blindspots where people have proclaimed you are good at, yet you strongly doubt?

I’d love nothing more than to hear from you if this resonates in any way. Are there questions you found work well? What obstacles have you tackled?