My 3 Most Epic (and Devastating) Entrepreneurial Failures & How You Can Avoid Them

on October 13, 2015 Resilience - Growth & Strength and Tags: , , , , with 0 comments
Bill Douglas - Lake Powell cliff jump Bill Douglas jumps off huge cliff in Lake Powell, UT, photographed by Andre Durand

It’s not a wonder that entrepreneurial people like Facebook. For like many on Facebook, entrepreneurs like to report the good news. We like to be successful, winning, report the good stats and block out the bad. Push through the pain.

It wasn’t too long ago that I wouldn’t have shared what I’m about to tell you. I was too vested in looking good, in winning, in being the Inc 500 success stories I’d built.

And you know, all my successes–which I like to think are pretty damn good, even though it has yet to ever feel like enough–they are all still true. The difference today is that I am willing to accept and even learn from the mistakes I’ve made.

For one, this sets me free. I feel lighter, smarter and better…to put it simply, when I tell it like it is, or was. The other major motivator for me is I’ve come to a place in my career, vision and life where I want to and am able to give back. I realize that there is something fundamentally missing in the wonderful network of entrepreneurialism… and that I, along with thousands of others, suffer greatly for it’s absence.

That missing ingredient is wisdom sharing… a mentor / coach who’s been there and completely gets what you are going through. I know what this would have and could have meant to me in my life and career. No, I do not regret any of the paths I took, for the hard way has offered me much — in this case, to share.

What I do regret is that there were no options. There were no mentors offering me not just “rah rah” you can “do it” coaching but some real honest guidance about the scrapes and cuts that we have become too willing to bear as entrepreneurs.

What could a mentor/ coach have brought to my life? I may have an extra $10 million or more. I could have enjoyed more time away and more balance. I may have kept a family together. Who knows what all it could mean.

But what I do know is that there is more than one way to learn this stuff. And the hard way is, well… hard.

If I can use my experience to help just ONE bullish, excited, stressed, crazy, overwhelmed entrepreneur save one of these missteps then my journey will be worth it 100 times over. If I can spare 20 of you from two or even all three of these errors, and many more, I will retire a very a happy man.

In this post I want to focus on what my entrepreneurial failures taught me with the intent to share & educate so that many others may avoid the same mistakes.

I’m a lifetime entrepreneur, infected by “the bug” early. I think this is a nice way of saying I’m unemployable, but that’s a given. Right.

In my 30 year entrepreneurial journey, I’ve had considerable successes, which means, by default,  I’ve had glorious failures as well.

As I journeyed the rollercoaster path each dip seemed, at the time, to be a unique situation. There was a reason and I was learning. Yet, it’s interesting how experience offers perspective. For as I look back now, it’s clear to see the patterns.

Sure, each “failure” was unique but underneath them all was a thread… a set of beliefs and behaviors that was ultimately giving rise to the dips and slips.

Here are the 3 most common drivers to nearly all my business struggles and failures. I have no doubt that I am not alone in suffering…

1. The Disease of Knowing.

Knowledge. Most often we think we have it. When we know something, it blinds us to what we don’t know. Therein lies the danger: I don’t know what I don’t know. I was young and bold and thought I had all the answers already. I didn’t seek help. I didn’t have the proper mentors and coaches for the first third of my entrepreneurial journey but even when that changed and I did have those resources, the disease of knowing greatly impeded my success.

There were plenty of great people willing to help me succeed; I learned that I needed to drop the ego, maintain a thirst for learning, and accept input as I worked towards success. And, then successes came.

Take aways to combat the Disease of Knowing:

  • Always seek help. Someone always knows more than you do, so find them.
  • Align with a few select mentors.
  • GET a coach and trust the process.
  • Never assume you know, and never stop learning.
  • Beginner’s Mind is your ally

2. Being an Opportunity Polygamist

As entrepreneurs, we see opportunities. Often, we see too many opportunities and we don’t want to let any of them slip away. My Entrepreneurial Masters Program classmates joked about “squirrels” being the death of us; as a matter of fact, we made the squirrel our unofficial class mascot to remind us to stay focused.

What if you treated your marriage like you treat your business? My guess is that the marriage would fail rather quickly because your spouse would be severely neglected.

As entrepreneurs, we must filter the opportunities we see based upon our own personal values, desires and abilities. Then perform diligence and decide on whether to pursue, shelve, or invest. Shelving or investing can be straightforward and not time consuming. If we choose to pursue, we must do so with vigor and complete focus.

Take aways to eliminate being an Opportunity Polygamist:

  • Opportunities are plentiful; time and energy are not.
  • Remain focused. Work toward very specific goals.
  • Commit to pursuit of a goal with blinders on, avoiding distractions.

3. Putting Me Last

There were many times, sometimes for months and even years at a time, where I neglected me: crazy hours, little pay, lack of fitness, not enough sleep, little to no delegation of tasks. Those were the worst times of my businesses.

As the CEO, the founder, the leader, I must take care of myself first. I must be compensated for my work. If I am not healthy and productive, there is no business. Creativity is certainly limited during unhealthy times. When I am vibrant and energetic, so are my businesses.

Take aways to contradict Putting Me Last:

  • Be selfish; focus on health and overall well being.
  • Pay yourself first.
  • Build rituals and structure into life.
  • Incorporate accountability to maximize productivity.
  • Exercise the mind and the body. Eat clean and get plenty of rest.

I’ve refocused my own life on helping others.

Being the mentor, the coach, the advisor to entrepreneurs brings me great pride and satisfaction.

Helping others grow their businesses and themselves to reach the pinnacle of success earlier and with less pain fulfills me.

This is my “why”: Empowering the Awakened Entrepreneur.

To learn more about the Awakened Entrepreneur and my quest to empower him/her, please visit here.


~ bill

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