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From Despair To Hope: How To Become An Optimistic Pessimist

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Last week we opened an odd can of worms asking if you would rather live in hope or die in despair. As with all of these articles, the point is to provoke your thinking about the choices you are making day-to-day, about how you are responding to whatever shows up in your life. When faced with challenges, should you take an optimistic view of what's happening or is the pessimistic view going to serve you better?

These are not simple questions and both the questions and answers reside on multiple levels of awareness and consciousness. Minimum levels of awareness and consciousness include what's happening physically, mentally, emotionally and spiritually. Many of these "levels" appear to be in conflict with one another; for example, if you are struggling to make ends meet, to keep a roof over your head and food on the table, how could you possibly be living in peace and gratitude?

The true optimist is not the one who puts lipstick on a pig and calls it beautiful. Having lost a job, a home or a relationship is not pretty and claiming that its wonderful is not being optimistic, it's being in denial. The true optimist is the one who recognizes the current reality for what it is, imagines a better future, and then has the strength, courage and willingness to dig in, make choices and do the work necessary to bring about that desired outcome.

While many would agree that the optimistic view is more healthy, there is a potential downside as well. Many who would describe themselves as optimistic tend to overlook conditions that are in the way, conditions that if ignored could actually lessen the likelihood of a good outcome.

The pessimist on the other hand will see the impediment or roadblock and label it as such. That's actually a pretty good skill to have but only insofar as you use the awareness to guide your choices toward a better outcome. The pessimist can also use the awareness of what's in the way as a reason not to move forward -- "See, I told you this was going to be difficult, it's just too hard, etc."

If we could cross pollinate the optimist and the pessimist, we might get a working hybrid, one that the true optimist already embodies either consciously or unconsciously. The pessimistic aspect will allow you to perceive the issues, challenges and roadblocks for what they are, without trying to put lipstick on them. For example, there's just no way to imagine something like paralysis as a good thing, and yet my friend W Mitchell whom I have cited numerous times in the past, is a living example of how to move forward in your life regardless of circumstances.

Stage Your Own Jailbreak

Mitchell, as he prefers to be called, exemplifies the ability to merge the benefit of realistic assessment, which many pessimists have, with the courage and willingness to move forward embodied in true optimists. He put it this way when talking to a group of juvenile offenders, kids locked up in prisons due to serious, often violent crimes:

This wheelchair was once a prison for me. However, in time, it became a vehicle and has taken me to audiences throughout the world ... to over 30 countries. Are mental wheelchairs holding you back in your own prison? I want to help you stage a jail break.

I know that the pessimists amongst you will even assail what Mitchell has been able to do, dismissing his remarkable ability to overcome the tragedies that befell him as something that only superheroes possess. The unfortunate thing about this dismissive attitude is that you get to be right! If you dismiss the willingness to imagine a better future then there is no way you will take even small steps toward that better future you won't allow yourself to imagine.

No one goes from zero to hero, or if they do, then they are rare birds indeed. However, if you find yourself in difficult circumstances, you still have choices you can make. Not all choices produce perfect outcomes, but they can be what I call directionally correct. Until you start imagining an improved circumstance, you will surely not make any progress. Even if you can't yet see the next step, you can still choose your attitude, even if it's as simple as "This sucks, but there must be a way out and I'm going to do what I can to find it."

So, use your natural pessimism, if that's what you have, as a way to recognize the reality of what's present, just as Mitchell had to accept that paralysis was going to be with him for the rest of his life. But from there, employ your optimistic side to imagine a way through and embrace whatever choices you do have. Quoting Mitchell again:

It's time to face facts: Everything is changing and it's NOT going back to the way it was! Now is the time to ... accept the new reality and move forward with PURPOSE, CONFIDENCE and GRATITUDE. ... Before I was paralyzed there were 10,000 things I could do. Now there are 9,000. I can either dwell on the 1,000 I've lost or focus on the 9,000 I have left.

So what about you? Are you going to allow your pessimistic side to win the day, denying your ability to move forward, or will you embrace the reality of what's going on and choose to move forward anyway. Embracing reality doesn't mean you have to like the conditions, just that you need to accept the reality and choose to do what you can to move forward.

What issues are you facing in life, ranging from health to difficult relationships to having lost your job, your home or your savings? If you have been more in despair than hope, what positive steps could you take if you were to imagine a more optimistic or hopeful outcome -- not some giant leap to perfection, just a small step or two that would help you move forward?

I'd love to hear from you so please do leave a comment here or drop me an email at Russell (at)

If you want more information on how you can apply this kind of reframing to your own life, how you can take a few simple steps that may wind up transforming your own life, please download a free chapter from my new book, Workarounds That Work. You'll be glad you did.

You can buy Workarounds That Work here.

Russell Bishop is an educational psychologist, author, executive coach and management consultant based in Santa Barbara, Calif. You can learn more about my work by visiting my website at You can contact me by e-mail at Russell (at)

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