Planning to Fail: Lessons Learned About College & Career Readiness

Author: Cindy Deschenes
April 4, 2018

Planning to fail in life is something most, if not all of us, never plan for. We don’t plan to fail, we plan to succeed— but life doesn’t follow our plans. Life throws curve balls at us from the time we are born. Life isn’t fair. As a woman who grew up on the land (by “land”, I mean I grew up on family traditional hunting territory which is off the reserve/reservation) with traditional teachings from her family and community, my life had a way of teaching me powerful and important life lessons through my circumstances and my failures which helped me succeed in post-secondary and in life.

My story of post-secondary success begins with some perspective and failures.

I was an unruly, disruptive, and rebellious high school student that came from not just illiterate parents, but a community of people that had never been to college or university (aka “the school of hard knocks”).* Transitioning to a new life at post-secondary was a path I would have to walk on my own.

But, how does one transition from being an unruly, disruptive, and rebellious high school student into a successful post-secondary graduate? How does one persevere through repeated advice that they are just not college material? How does one finally graduate from school when one failed at post-secondary more than once (I was kicked out of university six times— this number is higher if you count my college years)? Simply asked, how does one find success in post-secondary when you’re not planning to fail?

Might it be resilience? Might it be resourcefulness? Is it all about one’s paradigm? Or maybe it’s just sheer will, some luck, and lots of moxie! The answer is one we all know: there is no simple solution or crystal ball to provide the answer. As a therapist by trade, I’m inclined to offer several ideas though. But, regardless of what I think, I prefer you draw your own conclusions.

Planning to Fail: From Failure to Success the Hard Way

planning to fail
Planning to fail

I think we all understand, it’s a combination of things which helps one to find success when seeking to prepare for college, careers, or for life’s calling. But, if you’re anything like me and enjoy learning things the hard way, by all means, these are a few of my tried and true approaches to failure:

10 Contrary Teachings of Things to Try When Failing

  1. Don’t plan to fail. Have no plan and never make a list of things to address BEFORE even thinking of postsecondary – just wing it and see what happens.
  2. Have no support. Be too afraid to ask for help.
  3. Be unwilling to try new things. Be sure to avoid looking into things like banking needs, transportation/travel, and housing/accommodations.
  4. Never ever manage yourself. Your emotions, your personal life, your budget or future – if you happen to get into school, don’t make time to study and don’t apply for scholarships in advance.
  5. Procrastinate with everything.
  6. Do what everyone else wants you to do. Never mind about self.
  7. Break commitments to yourself, friends and family.
  8. Have no vision. Give no energy to school, application deadlines, classes or the location.
  9. Ignore your voice and the song in your heart. Learn to settle. Smash down that inner voice that dares to speak your heart’s desire. Entertain negative messages about failure.
  10. Internalize negative messages and believe them wholeheartedly. From the earliest negative messages, you have been fed – from not being smart or good enough to being undeserving. Believe it all, consume it daily and live by it.

If you do live by these top 10 Contrary Teaching Tips, you will find trouble, sorrow, and tragedy. Trust me— I have lived this list before. In many ways, item seven (break commitments to yourself, friends and family) was the most profound and devastating in my life during post-secondary. It was through my inabilities to walk with, and work with, the medicine of integrity and keeping commitments that I experienced two major losses in my life that significantly altered the direction in which I was heading.

The first was the loss of my grandmother. While in my early days of attempting to go to university, like many university freshmen, I became caught up in my social life and good times. On the eve of my grandmother’s passing, I chose a night of socializing and good times with my peers over visiting my grandmother in the hospital. She passed in the early morning hours while I slept off my Friday night fun. I never did honor her final request to go see her. The hurt I caused myself was indescribable and it has never fully healed.

The next loss was my first marriage. I stubbornly refused to do any more than necessary, to save the relationship, simply out of the egotistical need to be right. Instead of being willing to understand the other, we both adamantly stood our ground. As a result, due to ego, a wonderful relationship that did have potential to last a lifetime fell to ruins.

When Contrary Medicine Teaches About the Power of Tragedy

Like me, if you happen to get tired of failing or get tired of not planning to fail, then you may find yourself deeply questioning your purpose in life. This is the time to learn how to let go, listen, and take responsibility for your own life. Perhaps you are tired of seeing someone else constantly stumbling and failing: a child (your child), a student, a friend— but here’s the newsflash we all hear over and over— we cannot help anyone else unless they want help themselves. If we wish to help others in life, we do so by being a model. By planning to fail, we can be that model that others can look to.

One day shortly after leaving my marriage, I had a moment of existential crisis and sat outside my sister’s house contemplating what to do. The prevailing thought that came to mind was education. However, after a heart to heart with my teenaged son, I found the courage to begin following my heart and seeking my voice. With renewed inspiration, like a young eagle taking its first flight, I took the terrifying plunge to explore new directions in my life and headed west.

In short, I was taking responsibility for my future and becoming more willing to be in charge of my choices. While incredibly difficult, I left my tiny community, my personal support group, and network, to move thousands of miles away to pursue my educational goals. I wavered between fear and courage all the way to my new home in the west.

Nevertheless, I had been proactive prior to heading west and had been seeing a counselor to help me sort through a number of things that no longer served my purpose. I reached out to, and accepted help from, a professor friend of mine that helped me take these next steps. Planning to fail was no longer scary, but a welcome shift in thought.

Planning to Fail: Let go, Learn to Listen, and Take Responsibility

Get to know thy self

Get to know thy self. Listen to what the heart is calling for and become willing to explore possibilities. I learned the medicines required here were humility, a good dose of courage and openness. Through connecting with people, places, and things, I learned to pay attention. I learned what I liked, didn’t like and more importantly, to pay attention as much as possible to the life lessons that helped me develop personally. From the challenge of dealing with an irate authoritarian boss to the soul-satisfying sense one gets when volunteering, I made it a personal challenge to myself to learn about me in as many ways as possible through as many opportunities as I could handle. Most importantly, I made sure I had fun while doing them, even when disheartened from the disappointments life sometimes brings.

Understand personal and professional needs

Understand personal and professional needs. We each need to seek help to understand these aspects of self. While I was always open to mental health counseling, I truly overlooked the importance of self-care and mental wellness until my marriage ended in a soul and heart-wrenching manner. I learned I had to become willing to face, head on, the shadows and creatures that lurked in my own closet. Through spiritual, daily renewal and professional help, I came to learn how to break through the ties that had me bound to failure. This was not an easy journey, but highly rewarding for sure!

Find the song in your heart

Find the song in your heart – tap into vision and values before choosing a direction. While I did not have parents to guide me on my path for education, it was through talks with my friends, who were committed to their studies, and scholars I met along the way that I began to slowly connect with the song in my heart. Through a combination of my connection to my own Higher Power, taking time to think about my own lifelong desires, and meeting incredible people like Dr. Martin Brokenleg, the Coveys, the late Narcisse Blood, Dr. David Suzuki, the Dalai Lama, I learned to take time to connect with the song in my heart each time someone inspired me.

Let the magic happen

Let the magic happen. This allows for faith in yourself to flourish. Once I learned how to get out of my own way (by clearing out the attic so to speak), I was able to learn how to detect and connect with my life’s purpose. This was exhilarating because, for the first time in my life, I was truly giving myself permission to connect with my heart’s desires, dreams, and goals. I developed my own personal mission and vision. I learned how to make the right choice of being proactive.

Trust the process

Trust the process. Be willing to take healthy risks and be willing to trust the process. Growth is slow. Change is slow. Everything (with time and effort) will work out.

I dared to commit to a postsecondary institution and to follow this path ever since. This time around, however, I carefully took the time to find out what I was getting into. I began to ask questions beyond my goals that included everything from, “who can I go to for help with this?” to “what will I do to ensure I succeed?” I also asked myself additional hard questions like, “What will I do if I don’t get accepted into my school of choice?” The best thing I did overall was set aside my personal fears of people finding out I was “not smart enough” and learned how to seek out, then accept help whenever I needed. From times of grief and sorrow, to further harrowing curve balls life occasionally threw at me, I became an old hand at asking for help from people within my circle, to learning to ask for help from my Higher Power. These experiences of paying attention and taking personal responsibility have created all kinds of magic in my life and most importantly faith in myself.

I find it amazing as we begin to live by some of these seemingly simple things, life somehow becomes easier. As our paradigm shifts, so too, do the choices we make. We see the world differently, we behave differently, and consequently, we see different results.

I am now at a place in my life where I am choosing to be proactive. I choose my own weather no matter the path I may walk or journey I am making the choice. While it is not an easy journey some of the time, it is easily a remarkable journey all of the time. But, I will say, for every challenge and obstacle I’ve overcome, I have much to be grateful for. Wishing you all remarkable journeys!

* In Canada, there is a difference between university and college.


FranklinCovey consultant
Cindy Deschenes, Leader in Me Consultant

K8ey (pronounced kw/eh) and hello to you!

From Eastern Canada, and bearing the western name “Cindy Deschenes”, Cindy’s true given name in her language (Algonquin) translates to “She who sees with clarity, wisdom, or knowledge in both worlds”.  Cindy has a lifetime of experiences in working with Indigenous communities in the areas of mental health, education, and community. As a registered social worker, Cindy is both a Laugh Leader and Mental Health Therapist while also holding a position with FranklinCovey as Education Consultant.

Having developed educational and leadership training resources throughout Canada and abroad, Cindy is currently working toward earning a Ph.D. through the University of Saskatchewan’s College of Medicine. Her research aims to explore the connection between leadership development, The 7 Habits of Highly Effective People®, and The Leader In Me (TLIM) and its effects on individual mental health.

Cindy says this about herself, “While I sometimes wonder about my “clarity, wisdom and knowledge”, I always know that at any given moment, I’m resilient and resourceful. I’m a lifelong learner who has survived an impressive array of mishaps and tragedies including multiple child losses, holding a 6 time record of being kicked out of University, surviving over 14 car accidents, having been on fire 3 times in my life, having lived in the alleyways of Edmonton, Alberta, Canada with a 12-year old son, a repeat run-away dog and ex-husband-returned-to-friendship-man to having survived a direct face plant into mud while attempting to learn to paraglide (the list goes on).

While some may be taken aback that I could throw this out there so casually, I will add, that my life has also gifted me with extraordinary moments of beauty that include having self-delivered my son (doctor guided of course), having met the love of my life, meeting my grandchildren for the first time, having achieved a lifelong goal of living in Convent (yes, with Nun’s), having worked in an orphanage, having experienced the magic of living abroad for more than three months, having achieved the goal of earning an MSW to now working on earning my PhD. Whether it’s the utter shame and vulnerability that comes with having to publicly perform in a 1st year acting class or the joy of learning how to become a Laughter Leader, clearly I love adventure and more clearly a challenge.”

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