The Challenges Of The Road Less Traveled

When Playing The Long Game


The Challenges Of The Road Less Traveled When Playing The Long Game. Picture of a road in a forest reaching a fork, and the right hand lane disappears off into the unknown.


'The road less traveled' is a phrase popularised by M.Scott Peck with the book of that title. 

The theme is about:

  • The journey to maturity and growth
  • The need to confront life's difficulties
  • How to move through the hard and often painful process of change toward a higher level of self-understanding

I am using the phrase in the very specific context of the long game which describes an approach to any area of life that sacrifices short term gains for long-term wins.

This is about having a long term goal and taking the necessary steps now to set yourself up for a long term success.

This is rough, tough journey but the rewards are huge.



    You have to be willing to look like an idiot in the short term to look like a genius in the long term.

    [Shane Parrish]


Playing the long game

The first step to the long game and the acceptance of delayed gratification is the most difficult and negative.

You have to be willing to suffer today in order to reap enormous rewards tomorrow.

The long game is so hard to play because it involves taking a series of very small steps, that people rarely see,  persistently and consistently over a long period of time to reach an enormous and visible outcome.

The first question you need to think about is when and where to play the long-term game.

A good choice to play the long game is with things that really matter to you and things that compound such as: knowledge, relationships, and finances.

The second question you have to seriously consider is:

"Are you prepared to pay the cost?"

To do this requires you to ask yourself some very hard questions and to consider the second-order consequences of your decisions -  and the key question you will be asking is: "...and then what?"

The immediate effect of this is that you will have to be prepared for the reality that you be less effective, less competent and less efficient in the short term, in order to be much more effective in the long term.

This can be hard and it means being prepared to make a lot of mistakes and errors and even on occasions being prepared to look stupid.

Playing the long game, and paying the price for delayed gratification,  is hard enough when you are traveling on a well defined route such as qualifying to be doctor, a lawyer or an academic.

Playing the long game is doubly difficult when you are traveling on a road less traveled that is not well defined, where the milestones and metrics are not known when you start out on this journey.

Examples of the road less traveled are starting a business or any other form of entrepreneurial activity. Other examples could be launching any form of creative or artistic endeavour.






Features of the Road Less Traveled

The well defined route is clearly sign posted and has clear markers, metrics and milestones.

You do the courses, pass  your exams and qualify. Then you repeat the whole exercise several times until you are professionally qualified. Then your career follows a largely prescribed and predetermined path. Sure its tough but your direction of travel is very clear and you have clear milestones to mark your progress and give you the feedback you need to keep you on track.

On the road less traveled the route is often not clearly defined and does not have clear metrics and milestones.

I started working in the fuel business about 8 years ago - bringing refineries and resellers of refined fuel products [such as Aviation Jet Fuel and industrial use Diesel] together with qualified proceedable buyers. This is a tough business with many fraudsters and time-wasters.

The guy who was mentoring me told me 2 things that have stuck with me:

Firstly he said: "Stephen there is no instruction manual in this job nothing you can read that will train you or tell you what to do or how to do it. The only way to learn is on the job."

Then he said:

"The one thing that differentiates me from most other people in this business is that I am prepared to fail more times."

To put all this into context, over the 4 years that I knew him and worked with him he handled over 1,000 buyer inquiries and secured 9 different contracts with 9 separate Russian refineries of an average value of c$1bn USD per 12 month contract. He personally earned many millions of dollars in commissions. This man walked the talk.

Using some of my experiences over the past 8 years in this job here are a number of key issues that typically you will face on the road less traveled to delayed gratification and some approaches that I have used for dealing with them.






Issues Faced On The Road Less Traveled

[1] Working Out The Route

  • How can you figure out some useful metrics to know how you are doing?
  • How do you keep going when the going is tough and you are not sure if you are wasting your time?
  • How do you determine the green shoots of progress/recovery from the false dawn of another failure?
  • How do you separate and differentiate yourself from the herd?
  • How do you cope with the necessary personal and business dependencies on other people?


[2] Maintaining Your Mental Health And Well-Being

  • How do you cope when everyone else thinks you’re mad or deluded?
  • How do you cope with recurring disappointments and let downs?
  • How do you sustain yourself over the long term when it takes 10 to 20 years to succeed?
  • How do you stay healthy, positive and sane?

 

[3] Dealing With Other People

  • How much do you tell other people about what you doing?
  • How do you cope with other people’s inability to understand what you are telling them?
  • How do you cope with other people’s recurring disappointment at your lack of progress?
  • How do you cope with other people’s negativity?
  • How do you cope when other people are doing well and you’re not?
  • How do you cope with the feeling of letting your family and those close to you down?







Working Out The Route On The Road Less Traveled


Working Out The Route - on the road less traveled.


# How can you figure out some useful metrics to know how you are doing on the road less traveled?


# How do you keep going when the going is tough and you are not sure if you are wasting your time on the road less traveled?

  • This very much depends on the stage you are at.
  • If you are relatively new to your enterprise or endeavour, the usual advice is press on. However, if you realise very early on that you made a serious error of judgement getting into this, then in this instance it is a very good idea to bail out quickly before you do yourself [and the other parties involved] serious harm.
  • If you have been doing this for sometime and you are experiencing yet another major set back or let down then it is a sensible thing to undertake a quick review of your situation. Ultimately it all boils down to opportunity cost.
  • A decision to quit based on how you feel in the present moment is most probably the wrong decision.
  • The best approach to knowing when to quit is to have a predetermined set of "quitting criteria" which sets out certain key limits and boundaries beyond which you are not prepared to go.
  • This involves some important thinking skills and I recommend that you refer to and read the linked article Knowing When To Quit.
  • Over the long haul it is a good and sensible thing to periodically revisit your decision on "when to quit" as this will ensure that you remain focused and it will enable you to renew your commitment to the long game.


# How do you determine the green shoots of progress/recovery from the false dawn of another failure?

  • Short answer is you can't.
  • You will never know until you get there.
  • In the early weeks, months and years of your endeavour you will find that you quite understandably and naturally develop a strong attachment to a successful result.
  • As the years go by and you have several spins around the emotional and psychological roller-coaster you learn to manage your emotions and weaken your attachment to results. You have to, otherwise it will destroy you.
  • Learning how to embrace failure and uncertainty are necessary skills - not just for survival but  - because they are an intrinsic part of the process of getting to your ultimate major success.
  • You need to develop the quality of antifragility - that is, the quality of something that gets better, or thrives, in the presence of disorder.


# How do you separate and differentiate yourself from the herd?


# How do you cope with the necessary personal and business dependencies on other people on the road less traveled?

  • Short answer - with difficulty!
  • Personal dependencies on partners/spouses can be difficult - especially if the other person does not understand or fully support what you are doing
  • This can be manageable if you are not in anyway dependent on their financial support, but frankly if you are receiving any degree of financial support from a partner it is essential that they buy-in to what you are doing, and are 100% supportive.
  • In my experience it is worth investing the time and effort to ensure that your partner is kept broadly aware of what you are doing. Think of this in terms of expectation management.
  • Business dependencies on other people need to be grounded in good communications, good relationships, and controlling your emotions and not burning contacts.
  • You really cannot truly know someone’s strengths and weaknesses until you have been in action with them for a long time i.e. 12 months+
  • Knowledge is subordinate to results.
  • Identify early warning signals of “talk-walk” gap.
  • Look for early signs of those who “punch above their weight”.
  • Be wary of people who are distrusting and overly protective of disclosure – they are often hiding something and/or untrustworthy.
  • Ambition in a business partner is a good thing but identify early warning signals of people who: “don’t know what they don’t know, and don’t know that they don’t know”.


        




Maintaining Your Mental Health And Well-Being On The Road Less Traveled


When you're following your own path - how do you cope when everyone else thinks you’re mad or deluded?



# How do you cope when everyone else thinks you’re mad or deluded?

  • It's very hard is the honest answer and it is part of the price I have learned to pay for doing something different and what I believe will be extraordinary when it is complete. So I have learned not to be dissuaded by what other people think.
  • I learnt fairly early on in my journey on the road less traveled that almost everyone I knew outside of my immediate family and a very few close friends would never understand what I am doing both in terms of the actual business itself but also the long game aspect of it.
  • I very rarely talk about what I do except to those very close to me. I basically lead a double life. There is the face I present to the outside world with a scaled down, simplified and modified version of what I really do, and then there is the face I present to those who operate in my business world.
  • I do have a few "friends" who have basically told me I am crazy and who have either challenged me and/or laughed and sneered at me. It's amazing how badly people can behave. I have just learned to shrug them off and carry on. Its their problem not mine.

# How do you cope with recurring disappointments and let downs?

  • Short answer - you get used to it and learn to live with it.
  • As stated in earlier answers I have learned to embrace failure and uncertainty.
  • I also think you need to develop the qualities of antifragility as I said in that article: "...it allows us to deal with the unknown, to do things without understanding them - and do them well..."

# How do you sustain yourself over the long term when it takes 10 to 20 years to succeed?

  • I just keep on keeping on knowing that I am playing a long game. I monitor the metrics so I know where I am and how I am doing. I just keep my head down and carry on one step at a time, one day at a time.
  • I understand and apply many of the principles outlined in this website on mental models and productive thinking
  • I also have a deep seated belief and confidence in myself, my life purpose and what I am doing.
  • This is who I am. This is what I do. How could it possibly be any other way?

# How do you stay healthy, positive and sane?

  • I take care of my mind and body in all the usual ways. I exercise moderately and daily.
  • I practise mindfulness and what I call the balanced toolkit approach to life.
  • I take great pleasure in the simple joys of life.





Dealing With Other People On The Road Less Traveled


Dealing With Other People On The Less Traveled Road.


# How much do you tell other people about what you doing?

  • Short answer -  very little!
  • I keep it on the "need to know" basis and generally, the less they know the better.

# How do you cope with other people’s inability to understand what you are telling them about what you are doing?

  • I have learned not to tell them. I just don't talk about my business.
  • If asked in social settings I have several simple answers that are grounded in the truth but sufficiently boring to encourage people to change the subject.

# How do you cope with other people’s recurring disappointment and negativity at your lack of progress?

  • Most other people don't know what I do and I don't talk about it so this doesn't arise very often.
  • With those few non-family members who do know, I just tell them how it is, or sometimes I just avoid them.

# How do you cope when other people are doing well and you’re not?

  • This can be hard but I just focus on what I am doing.
  • Comparisons are largely meaningless.
  • Nobody truly knows the inside track on someone else's life.
  • I also know that I am playing the long game and the rewards are enormous and deservedly so.

# How do you cope with the feeling of letting your family and those close to you down?

  • In my darker moments this has been crushing.
  • Personally I have been blessed with a very supportive family.
  • I don't dwell on negative feelings and I always return to the task in hand and keep on keeping on.
  • The long game is a tough game but ultimately an enormously rewarding game.






The Road Less Traveled - Further Resources

Here are a number of touch points with other key articles on this site:




Next Article:

How To Benefit From The Unseen Margins - 5 Key Tips For Success


Return:

to: Mental Models

Or to: Walking The Talk

Contact me



English Chinese (Traditional) Russian French German Italian Spanish Vietnamese



LATEST ARTICLES

  1. The Transformative Power Of Acceptance

    Experience The Power Of Acceptance. This website contains about 500,000 words. You could read every single word and it wouldn't make any real difference to you. You might become better informed, but t…

    Read More

  2. Inversion - The Power Of Opposite Thinking

    How To Avoid The Unwanted Outcome. The power of opposite thinking, also known as inversion, lies in its ability to stimulate creativity, enhance problem-solving, and provide a fresh perspective on cha…

    Read More

  3. Are You Aligned With Reality? Or Do You See What You Believe?

    We tend to see that which aligns with what we believe, and to act upon that rather than acting on reality. Being aligned with reality starts with a clear and accurate understanding of the world. It me…

    Read More

  4. The Law Of Response and Outcome

    A New Approach To A New Life At time of writing we are entering a new year which is traditionally a time of making resolutions to change our behaviour and improve the quality of our lives. And yet pow…

    Read More

  5. Clear Thinking - Turning Ordinary Moments Into Extraordinary Results

    There are two ways to handle the world - try to predict, or try to prepare. "Clear Thinking" by Shane Parrish, published in Oct 2023, is a laudable testament to the art of cogent thinking, and will be…

    Read More

  6. Self Dialogue - Working With Your Many Selves

    Self Dialogue Is About Working With ALL Levels Of Your Mind. The key to effective self dialogue is to have tools, techniques and resources that work with all levels of your mind. This simple self-faci…

    Read More

  7. The Balanced Brain - The Ultimate Route To Personal Transformation

    How To Experience The Benefits Of A Balanced Brain. Underpinning all of the belief systems and practices that offer routes to personal change, transformation and spiritual growth is the balanced brain…

    Read More

  8. How To Make Better Decisions - By Avoiding The Narrative Trap

    To Understand The Truth We Have To See The Whole Picture. One of the best ways to make better decisions is to have a deeper understanding of the many things that might stop that happening. To understa…

    Read More

  9. The Greatest Love - The Most Important Relationship You Will Ever Have

    Yet Most Will Never Know It Everyone of us has a place, in our hearts there's a space, that is home to the greatest love of all. This love transcends everything we think we know about the world of for…

    Read More

  10. Everything Is Connected And Why You Don't Feel It

    ...And Why It Matters As human beings we are skating on very thin ice with our sense of self and certainty about "how things are" and what we like to think of as reality:

    - What if everything we think…

    Read More

  11. Who Is In Charge Of Your Brain?

    How Not To Be Stupid. Who is in charge of your brain? This is not a silly questions. It matters because the outcomes that you experience in your life are determined by how you respond to the events th…

    Read More

  12. How To Be A Winner On A Very Large Scale

    The Incredible Benefits Of Selective Attention. This is not a typical article about how to be a winner. We are not going to talk about goal setting, the importance of habits, the power of focus and al…

    Read More

  13. The Metagame Approach To Life

    How To Achieve Your Biggest Objectives. The metagame approach to life is all about winning and achieving your biggest objectives by: - Understanding the bigger picture
    - Being better by doing things d…

    Read More

  14. Shantideva - The Way Of The Bodhisattva

    Walking The Path Of Compassion. Shantideva the 8th century Indian Buddhist sage is famous for his treatise "The Way of the Bodhisattva" delivered as an extended teaching to the monks of Nalanda monast…

    Read More

  15. Reframing History - Deconstruction And Discussion Not Destruction

    History is always about context, not imposing our own moral values on the past. For those of us fortunate enough to live within western democracies, we are living in an age where a vociferous and into…

    Read More

  16. Tao Te Ching - Connecting To Your True Source Of Power.

    How To Be Lived By The Tao. The Tao Te Ching is one of those books that many people read, few understand, and even fewer put into practice. The only way to know the Tao is to experience it, and it is…

    Read More

  17. How Things Really Are - The Inbuilt Design Flaws

    Chaos, Disorder And Decay Is The Natural Order Of Things. Nobody has the perfect life. We all struggle and strive to attain health, wealth and personal happiness. Yet these three big areas: our health…

    Read More

  18. Intuition Or Anxiety - Are There Angels Or Devils Crawling Here?

    How To Tell The Difference Between Intuition and Anxiety. How do you know whether the voice of your intuition is real or just the product of your inner anxiety? Several months ago I was having a drink…

    Read More

  19. What Is Truth - How To Tell A Partial Truth From The Whole Truth?

    How the truth and nothing but the truth is often not the whole truth. My great aunty Flo broke her arm and died. It is true that she broke her arm in 1923. It is also true that she died in 1949. But t…

    Read More

  20. Duality And Life Beyond Your Thinking Mind

    Duality and life beyond your thinking mind focuses on the limitations of time, foreground and background, duality and "stuckness". The first aspect of duality and life beyond your thinking mind focuse…

    Read More

  21. The Conscious Mind Is Limited - Be Aware And Be Prepared

    Being aware is the first stage of being prepared. The conscious mind is limited in so many ways. There are some who would argue that there is no such thing as conscious thought and that it is represen…

    Read More

  22. Your Inner Map Of Reality - Here's Why You Think The Way You Do

    The big picture of how your inner map of reality creates your feelings, thoughts, and behaviours. Your inner map of reality is based on the filters of your own ethnic, national, social, family and rel…

    Read More

  23. The Failure Of Cancel Culture - Suppression Not Engagement

    Why we need to wear our beliefs lightly and develop negative capability. Throughout history people have campaigned to fight beliefs, ideologies, and injustices that they perceived to be oppressive, di…

    Read More

  24. 4 Big Reasons Why We Get Stuck In Our Attempts At Personal Change

    Most People Spend Their Entire Life Imprisoned Within The Confines Of Their Own Thoughts. This first of the 4 big reasons why we get stuck is, in my view, the most important. The "self-help industry…

    Read More

  25. How Do I Change And Why Is It So Hard?

    We Would Rather Die Than Change, And We Usually Do In my experience, the vast majority of people who say they want to change don’t change. Most people reading this won’t change because they don’t real…

    Read More

  26. The Illusion Of A Separate Self - Windows 11 With Self Awareness!

    Beyond the content of your mind you are so much more than you think you are. When we talk of "myself" this is the conventional way of referring to our self image which is in fact the ego's constructio…

    Read More

  27. Finite And Infinite Games - Dazed, Confused & Ultimately Transcendent

    This is not an instruction manual, it is a wake up call! Over this past week I have read Professor James Carse's highly regarded "Finite And Infinite Games - A Vision Of Life As Play And Possibility"

    Read More

  28. The Gap And The Gain - How Your Brain Sabotages Your Happiness

    How Your Lizard Brain Sabotages Your Happiness We are hardwired to measure our progress in any and all areas of life where we have goals and aspirations. We can't not do it. But what we measure and ho…

    Read More

  29. How To Wake Up - 4 Simple Practices To Help You Wake Up Now

    So What Exactly Does It Mean to Wake Up - What Is "Enlightenment"? There is nothing magical, mystical or mysterious about waking up we’re actually having glimpses of enlightenment all the time. Enligh…

    Read More

  30. Situational Communication - Different Strokes For Different Folks

    Situational communication is about taking account of 3 often ignored factors about the other person. You are a situational communicator when you recognise that effective communication is not an event…

    Read More



Get new posts by email:









Zen-Tools.Net





Support This Site