Why perfectionism is a death trap for entrepreneurs


I started out life pretty sloppy; inherited the trait from my mother. Being sloppy didn’t hinder her from being Phi Beta Kappa, receiving a Harvard Law degree, and successfully practicing law for more than 50 years – 50 with the same law partner! Only the CIA’s best could even begin to decipher her handwriting. And I followed her example by getting consistent Ds in my penmanship classes. However, technology saved the day for her. Technology in the form of a dictaphone. For those of you not ancient enough to be familiar with this device, it was a very early voice recorder used by lawyers, doctors, and executives to transcribe their notes or documents, to be typed up by their secretaries. For those of you too young to know what a secretary was, secretaries were almost all women, though I did have a male secretary briefly, who performed administrative tasks for one of more managers or partners. Proficient typing skills were a pre-requisite. My mother told me she purposely never learned to type so she could evade being sent to the secretarial pool. Being a male I didn’t have that problem, and for reasons I can not recall, took a typing class with my friends one summer. Touch typing was something I had over my Dad, who was what was known as a hunt and peck typist. He used two fingers to peck at his keyboard! And touch typing came in handy in ways I never would have foreseen.

My father was a MIT-trained electrical engineer who never heard or saw anything he couldn’t find fault with. Rebelling against his perfectionism as an adolescent probably accounted for half of my anti-perfectionism.

There is a simple story of how I became a perfectionist: I was introduced to the power of computers to change, modify, update and correct any document with ease. All of a sudden my latent perfectionism rose its head and I proofread and copy edited all my emails and other documents with a vengeance, and without the aid of a spell checker, which had yet to be invented. Once I became a perfectionist about written documents it soon spread to all of my business interactions. And it seemed to a successful strategy for me, as I rose from Product Manager to Vice President of Product Management, and got to direct QA, marketing, sales, accounting, and manufacturing as well! Everything, in other words aside from software development. However, as my responsibilities grew exponentially I soon learned the bitter truth about being a perfectionist, especially in a high growth startup: it does not scale. So if you don’t read anything else in this post read the next sentence:

Perfectionism does not scale! The old saw that the perfect is the enemy of the good soon proved true for me as an executive.

So if you are now a perfectionist or have latent perfectionist tendencies read the HBS article How Perfectionists Can Get Out of Their Own Way by Alice Boyes or at least this post. It may save your career! Alice Boyes lists five ways perfectionism can sabotage the workplace.

1.Struggling to make decisions or take action

Perfectionists are motivated to make the absolute best choice — even when doing so isn’t strictly necessary. This can lead to decision paralysis. While you might get away with being a perfectionist in a large slow moving old company, it’s death in a startup. Because startups are decision machines! as I’ve written elsewhere in my posts on decision making in startups. Execs and managers, in fact any decision maker in a startup have to make more decisions faster than they ever have in their life. And with an average of about 80% of the information they would have in a mature company.

2. Worrying excessively about sunk costs.

Perfectionists can spend too long working on marginally productive activities before moving on. Learn from your mistakes. Don’t make the same mistake twice. And be creative about your mistakes, don’t make those of your peers, superiors, staff or mentors. And in the immortal words of Baba Ram Dass, Be here now. I can not tell you how many thousands of hours I’ve wasted worrying about mistakes I’ve made and what I should have done. In sports they call this the Woulda, coulda, shoulda problem.

3.  Avoiding challenges to avoid failure

Perfectionists want to feel absolutely ready before taking on challenges. This can lead to holding back from advancement or leadership roles. Personally I never had this problem, but I’ve seen it in others. It can result in sub-optimal performance and stalemate one’s career. Once I learned to live with, admit, and learn from my mistakes I was ready to take on any challenge, including starting half a dozen companies.

4. Applying their high standards to others.

Like my father, as a perfectionist I became a champion nitpicker. When you have 50 or 100 people in your group, trust me, there’s an infinite number of nits to pick. After driving most of my staff half-crazy I learned a couple of ways to combat my perfectionism.  One, management by exception. The other, taken from the battle field and then the hospital emergency room is triage. Management by exception means only dealing with errors if they make are a difference that makes a difference. As in basketball, no harm, no foul. Triage is the process of prioritizing the severity of problems and paying attention to and attempting to remediate only the high priority problems. Trust me, if you are rigorous in applying these two techniques, which are much harder to practice than to type, your management breadth of reach will begin to scale.

5. Ruminating about weaknesses, mistakes, and failures

This is just the general case of number 2, Worrying about sunk costs. In sports again the saying is, It is what it is. Athletes are often quoted when asked questions about coaching decisions are trained to say (and to believe) I don’t worry about things I can’t control. This is a great place to put in a plug for
The Serenity Prayer, which says in part, God grant me the serenity to accept the things I cannot change; courage to change the things I can; and wisdom to know the difference. 

If you have read this far and see yourself as a perfectionist or having perfectionist traits the author goes on to describe how to minimize the downsides of perfectionism.

  1. Learn from successes.
  2. Develop heuristics to enable faster decision-making and action taking.
  3. Ask yourself “How could I improve by 1%”?
  4. Learn strategies to disrupt rumination.

Just to amplify point one. Learn from successes is something I preach to my mentees to practice with their teams. Your goal is to emulate successes, not emulate failures. So make sure to balance learning from your failures with learning from your successes, whether that be winning a prize customer, meeting your revenue projections, or just everyone having a good time at a company picnic. It’s just as important to understand what the drivers of success are as what are the mistakes that lead to failure.



Author: Mentorphile

Mentor, coach, and advisor to entrepreneurs, small businesses, and non-profit organizations. General manager with significant experience in both for-profit and non-profit organizations. Focus on media and information. On founding team of four venture-backed companies. Currently Chairman of Popsleuth, Inc., maker of the Endorfyn app for keeping fans updated on new stuff from their favorite artists.

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