Issue #19 - Should I Stay Or Should I Go?

When I was a teenager, I was drawn to the rawness of the music that emerged from the punk era. There was something about the sound and look of these anti-establishment personas that I found mesmerizing. This period was influential on me and I remember how I evolved, as I started wearing Doc Martin shoes, a black leather motorcycle jacket and a silver hoop earring (to my fathers chagrin). I also changed up my hair style, growing out the top while shaving the sides.  My buddies and I started cutting each other's hair using clippers on the  #1 setting.  We  were inspired by the extreme sking icon Glen Plake and on more than one occasion we would use Jello to spike our hair before going to a concert or our local ski hill. My newly found fashion sense was a nightmare for my parents but I recall feeling a sense of liberation in being able to visually express my inner rebel tendencies.

During that time of my life, one of the bands that was formative to my style wasThe Clash. The cover of the album London Calling has an image of bassist Paul Simonon on the stage of a hazy New York venue–capturing him in the act of smashing his bass guitar.  Every time I see this picture, it still stirs something within me; a reminder of the pent up youthful tension at that moment in my life with a desire to push back against the status quo. 

Over the years my fashion sense has evolved, but I still have fond memories of this unique phase of my life and a soft spot for the influence of punk music. With that, I love to pay homage to my musical roots by proudly wearing one of the many band t-shirts that I have in my collection.  My favorite shirt features the London Calling album artwork with its iconic pink and green lettering that I have since come to learn was inspired by Elvis Presley. There has always been something about identifying with the anti establishment that I have found appealing and this perhaps may have teased out my future path in pursuing entrepreneurial endeavors.

While I love the album artwork of London Calling, my favorite Clash song is Should I Stay Or Should I Go, from their album Combat Rock. The song’s chorus repeats the lines “Should I stay or should I go now? If I go there will be trouble; And if I stay it will be double.” The lyrics from this legendary song are thought to have had dual meaning. The first being the common dilemma of whether or not to stay in a romantic relationship.  The second teasing out clues about the strained relationship between guitarist Mick Jones and lead vocalist Joe Strummer that would lead to the band breaking up in the mid 80’s. While the song's message may have been contemplating the compatibility of personal relationships, I think the meaning can be extended to question the relationship entrepreneurs have with their venture.

The world of being a founder is not for the faint of heart and I would never suggest that it is something that everyone should do. Launching a startup is incredibly hard work, with the mortality rate high and the odds of success low.  Of 100 startups that begin today, in 5 years there will be 20 remaining, 5 will do more than $1M in revenue and of those only 1 will actually build a meaningful, sustainable, scalable and ultimately saleable enterprise.  However, for the right individual, there is something about these odds that we find intriguing.  Like a moth drawn to the flame we choose to pursue this career path of high risk and (potentially) high reward.

As founders we love to use our curiosity and creativity to cast a vision of what is possible. In the process we act as time travelers, teleporting into the future to see the potential and then coming back to the current reality to do the work to create it. This means showing up consistently to put the building blocks in place that transform what you have imagined into reality. However, reality rarely goes as planned and often we encounter roadblocks and obstacles along the way.  In most cases this is resolved through creative problem solving combined with persistence and determination to overcome the challenges. But what should you do if you cannot see a way around or a clear path forward? How do you know if what you are building has the chance to be part of the ultra rare one percent of businesses? 

I hate bad advice especially when it comes in trite sayings or easily passed along pithy quotes. One of these sayings goes "winners never quit and quitters never win."  There is a partial truth to the quote in that as entrepreneurs we need to have grit, resolve and sticktoitiveness when you are embarking on any entrepreneurial journey.  These attributes are simply the table stakes required whenever you are starting a startup knowing that in most cases it is going to be harder than you imagined and take longer than you think. 

The real art is knowing when you should persist, when you should pivot or when you should potentially put the proverbial "bullet in your business" and save your resources for another day. 

The truth is that based on the high mortality rate in business and with the odds for business success being very low, that in the vast majority of entrepreneurial cases, the risks vastly outweigh the possible rewards. Measuring our results not just in terms of financial metrics but also within the context of lost time and opportunity costs is of utmost importance

The word entrepreneur means "to embark on" and according to the dictionary is described as "an individual who creates a new business, bearing most of the risks and enjoying most of the rewards." Founders are literally creating something out of nothing within the context of risk and uncertainty.  By default this means a high probability of failing however it is this very exposure to risk that makes an opportunity worth pursuing. There is no satisfaction from walking a tightrope that is laid on the ground. It is only when it is raised up and the consequences high, requiring flawless execution that we consider it to be a meaningful accomplishment. Furthermore it is not a skill to simply stand on the rope and maintain balance.  The key for accomplishment is that you need to maintain balance while making meaningful progress over reasonable time.

I love Deming’s quote "In God we trust, all others bring data." It speaks to the importance of having meaningful ways to measure progress to ensure that we are never confusing activity for accomplishment. It is easy to fall into the trap of being busy and not taking the time to step back and consider if we're advancing or if the business model is designed or timed right. Furthermore we often allow our investments of time and money to instill a sunk cost bias that only further clouds our judgment about when we should continue forward or call it quits.

It is important to understand that quitting on a business opportunity is not the equivalent to quitting on life.  You are either winning or learning in life.  Choosing the right time to quit is simply understanding that with what you have learned you are choosing to prioritize your most important resource (your time) to find a better opportunity and/or time for the future.  

So with your venture how should you know if you should stay?  In my experience you should continue if you are seeing meaningful progress over a reasonable time towards your goals, vision and mission. Along with this progress, you also need to remain hopeful that your idea has the possibility of achieving the future outcomes that you have imagined. It is up to each entrepreneur to determine the right measurable quantum for an opportunity and the required time horizon to achieve it.  My personal expectations are that within 5 years (reasonable time) an opportunity must have the potential to become a one percent business. 

How do you know when you should go?  First off I have to admit that this is not something I am good at. I hate quitting. It is actually against my DNA and in many cases has resulted in deferring the inevitable failing of several of my past ventures.  I am an eternal optimist with a stubborn nature and for most of my life I have resisted confronting the glaringly obvious.  However, failing fast is now something I prefer.  My choice on whether to persist, pivot or put a bullet in the idea, comes down to when I run out of either hope or the resources I have allocated to an opportunity.  In some cases it is both. However it is my point of view that hope is the much bigger factor as I firmly believe that a founder with hope, confidence and a clear vision for the future will inspire and attract the resources needed. 

If however you feel hope waning and you are at a place where you are frustrated with your progress.  If you believe that you have given your best and are now asking the question if you should quit.  Then there is a good chance that you are likely already too late and are suffering from some sunk cost bias that is causing you to defer the decision. 

I know that feeling first hand and I tell the story in Start Up Santa, of how with my first company, I refused to see that my business model was flawed. I falsely believed that by raising more money I could fix it.  I have since learned that there is not enough money in the world to overcome hubris and/or resolve a broken business model.  What held me back was my stubborn unwillingness to surrender, a fear of failing, my sunk cost biases and my biggest stumbling block being a concern about the judgment of others.  

The committee called “they”(what will they think? what will they say? what will they do?) has often clouded my judgment in making the right decisions about what is best for my life and business. I have learned that being concerned about what others think is largely a waste of time. Firstly because  people are not really thinking about you at all;they are busy thinking about themselves. Secondly, by being concerned about what other people think, you are unwittingly giving your power to others and in the process dumbing down your potential and pruning the possibilities for your life.  

In my experience the best way to overcome the concern of what other people think is to use a “regret minimization” approach. Fast forward to your 80 year old self and with the decision you are contemplating ask yourself the question: will I be glad I did or will I wish I had? ‍

If you are unsure whether your current venture is the right opportunity, facing a “should I stay or should I go” quandary,  here are some questions for you to consider: 

1. Do you believe that the current macro trends are working for or against your current business vision?
2. Do you see that changing for your benefit in the near future?
3. Do you still have hope in seeing your vision become reality within the timeline and resources you have allocated? 
4. Knowing what you know today would you make the same investments of time and money to start your business?
5. Who’s opinion of you really matters and is your concern of what others think holding you back from making the right/best decision?
6. What are the opportunity costs of choosing to stay the course?

As a founder, my hope for you is that you will use your curiosity and creativity to imagine as big and bold a future as possible. That you will act courageously and invest your life resources in building something great.  A business that creates considerable value for both people and the planet and in doing so provides you with enjoyment, satisfaction and meaning. However if you are frustrated with your progress and arrive at a place where your hope and resources are waning, then make the choice to go. In the words of W.C. Fields “If at first you don’t succeed, try, try again. Then quit. There is no use being a damn fool about it.” 

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