Do Differently

Quick Summary: Carefully and regularly review errors and traps you and others have made to avoid them.


All of us have regrets about some of the things that we have done or failed to do in the past.  They occur in our personal as well as our professional lives.  The very nature of being an entrepreneur or CEO of a startup means that there will be many uncharted waters that need to be traversed.  Learning from your past mistakes and those of others is key to survival.

We have all heard the proverb that “hindsight is 20/20” and the quote: “Those who do not learn from history are doomed to repeat it.” (George Santayana).  Additionally, all of us have said: “If I could have done it differently, I would have…”.  And finally, “I wish I had known that…”.  For entrepreneurs, it would not be surprising if these statements are weekly occurrences.  I know because it has happened to me and still happens – far too often.  In preparing this article, I quickly reviewed my email contact lists and LinkedIn contacts.  I identified 170 entrepreneurs or startup companies that I have worked with over the past several years.  Through September 2018, I have been involved with 62 different entrepreneurs or startups to one degree or another.  I thought back to my discussions with each of these entities and developed the list below.  Each of the 54 statements reflects what “they should have done” for their business or idea.  The “they should” could be “I should” or “We should”.  It doesn’t matter if the issue was personal or group-based.  In the end, the entrepreneur or CEO is responsible whether it was their error or that of their collective staffs. 

When I work with companies, I often say, “I want to help you make new mistakes and not repeat the many mistakes that I have made or seen over my career.”  Many think I am kidding; I am not.  Of the list of 54 items below, I have made at least twenty-one of them!  To protect my ego, I won’t identify which were mine and which were others.  In only a few cases were the items listed singular events involving one company.  Unfortunately, I believe this is a fairly common list.

Think of each item in this list as a road hazard sign, warning of what may be ahead.  Only the issue and not the solution is provided. Most of the items are discussed in other articles in this collection.  Searching the website by article title or keyword should lead to the appropriates articles.  The list is divided into eight sections.  Many of the items could have been listed in other sections, so it is best to review all the items.   As one sentence summaries, some of the items may not be clear.

Perhaps the best use of this list is to review it weekly and candidly review the past week’s activities to determine if any of the items apply and, if so, what quick corrective action can and should be taken.   Unfortunately, as time goes on, I am afraid that I will be adding to the list based on what I do and what I see others doing!



  1. Should have focused more on revenue and less on operations.
  2. Should not have been so concerned about profitable revenue first.
  3. Should have spent more time developing a recurring revenue model.
  4. Should have spent more timing realistically forecasting sales and revenue.
  5. Should have weighed revenue opportunity against cost before proceeding.
  6. Should have paid more attention to terms, collections, and cash management.


  1. Should have listened more carefully to prospects to help understand their needs.
  2. Should have focused on a narrower segment first.
  3. Should have captured sales impediments to better understand sales hurdles.
  4. Should have been more flexible with initial pricing to get customer traction.
  5. Should have taken more time to understand why competitors do what they do.
  6. Should have tried to better understand why some markets/applications have gone unaddressed.
  7. Should have hired local guides that knew other markets better than we did.
  8. Should have spent more time understanding the differential advantage that we offer.
  9. Should have spent more time simplifying our message.


  1. Should have said no to prospects that we knew were not equipped to support our product.
  2. Should have realized that customers do not have the same sense of urgency to change their existing methods/systems to implement our offering.
  3. Should have said no to prospects that we knew we did not fit.
  4. Should have spent more time understanding what it would take for customers to implement our product in their environments.
  5. Should have spent more time figuring out our long-term distribution strategy.
  6. Should have been done a better job of qualifying customers and understanding their revenue potential.
  7. Should have spent less time on proposals and detailed client work without a commitment.
  8. Should have had much simpler, easier to understand pricing.


  1. Should have spent more time planning our roadmap, its requirements and timing.
  2. Should have considered implementing simpler systems to save money and first understand what we would need in the long-term.
  3. Should have thought through how to scale the business earlier.


  1. Should have gotten our MVP out faster to obtain independent customer feedback.
  2. Should have better understood how long it would take to get to cash flow breakeven.
  3. Should have delayed pursuing national (out of area) opportunities because of their extra time and expenses.
  4. Should have taken time early on to better understand international product and business requirements.


  1. Should have more carefully differentiated between what we “could” do and what we “should” do.
  2. Should have followed my "gut instinct" instead of waiting.
  3. Should have been more careful in selecting partners.
  4. Should have spent more time figuring out what we could outsource instead of doing tasks internally.
  5. Should have made tough decisions faster.
  6. Should have developed and stuck to requirements documents to prevent creeping features and delays.


  1. Should not have hired my best friend or relative.
  2. Should have held people more accountable.
  3. Should have realized how much time and diversions raising money would take.
  4. Should have trusted less and verified more (sales forecasts and development plans)
  5. Should have made tough decisions about employees earlier.
  6. Should have spent more time understanding what our true core competence was instead of relying on being first to market.
  7. Should have kept our business focused on our core competence instead of being diverted.
  8. Should have developed key business metrics.
  9. Should have started some standardized processes earlier.
  10. Should have developed shared goals for everyone.
  11. Should have been more frugal.
  12. Should have realized that as an individual consultant, my business could not scale.
  13. Should have planned better for continued ongoing support for custom solutions.


  1. Should have worked harder to develop and maintain better work-life balance.
  2. Should have thanked people more often and acknowledged their efforts.
  3. Should have been more patient with others and the business.
  4. Should have listened far more and talked far less.
  5. Should not have shown my anger.
  6. Should have taken the time to respond and not react.
  7. Should have delegated more often.
  8. Should have reviewed a list like this on a regular basis!


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