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Every day we are faced with decisions, and to feel in control of our day or of our life, we try our best to plan our way around the unpredictability of being entrepreneurs. We try and make sense of ourselves and what needs to be done by adopting productive habits, making lifestyle changes, using guidelines or plans to make this possible.


But when I say that you were better of hoping than planning it isn’t about the minutia of everyday scheduling or fitness plans – you can’t hope for a better body, well you can, it’s just likely you won’t get it.


I am talking about your bigger picture, your plan for yourself, and where you see yourself in your future. And I think that planning, at this level, simply doesn’t serve us in the way we think it will.


Here’s why you are better off hoping than planning:


The Future Isn’t Real

There is a narrative that we accept, which is that it is possible for us to determine and control the future.


We want that to be true, that we are able to predict ten, twenty years in the future with relative certainty, because the alternative is uncomfortable. The flip side of not having control about our future means that we have to accept that tomorrow is unpredictable, that change happens, and that nothing is guaranteed.


It implies that our sense of security, a lot of the time is built upon a foundation of presumptions and assumptions. In may cases success will be defined by your skill becoming better at predicting a future that you accept as unpredictable. It is educated guess-making.


If the future isn’t real, and if in your heart of hearts you really know that it’s true, why do we put so much time and energy into planning?


When we hope we accept that it can go either way. That the outcome is not only determined by our capacity alone, but a mixture of forces that are out of our control.


When we hope we focus on optimism rather than pessimism. Click To Tweet


Because surely if you need to control something, plan it out, have that one plan be irrefutably the likely outcome – there is a part of you that is fighting against the possibility that it will fail. Our long term plans is based on the pessimism that everything will fall apart unless we have that plan.


What would change if we were more optimistic and held onto our hopes and accepted the fears inherent in what we want for ourselves? That both are fact, and that we create short term plans to keep the steer the ship. What is the cost of deluding ourselves that we can determine the world 5 years from now?


Postponing Happiness

I speak to so many entrepreneurs who say these words:

“I can’t wait do that when I (fill in blank).”


We postpone our happiness. A lot of time we don’t feel worthy of it. Click To Tweet


Like our overachieving mindset sets up the belief that we somehow much earn our happiness. And a lot of it is tied to how money (or the lack thereof, by our standards) prohibits us from enjoying what we love.


The problem with this is that when you are in a pattern of postponing your happiness, there could likely be a part of you that sees the sacrifice as fuel for your sense of progress. That without saying “when I (fill in blank) then I will” you worry that your immediate happiness will breed contentment and stall what ever progress you have made – leaving you complacent and vulnerable to failure creeping up on you while you are busy enjoying yourself.


It is that vigilance that convinces us that we are in control. As if the bank balance of our ‘entrepreneurial karma,’ where if we sacrifice now, for long enough, will guarantee success – because that feels fair right?


John Lennon said: “Life is what happens while you are busy making other plans.” Click To Tweet


When you shift from a need to control the future, postponing your happiness, and accepting the unpredictability of your future as a natural part of your life, you are able to become more present and invest time into what you love to do.


When you let go of the expectation that your plans will one day bring you happiness, and take the less resolute stance of hoping everything works out you set yourself free to enjoy the life you have today.


Odds are you might be happier, more grateful, and more creative, which in turn will spill over into what it is that you are working on.


Your Sense of Failure

Even with so much writing out there about how failure is a natural part of learning and innovation we are still deeply risk averse and for many failure is a taboo topic to talk about openly. And mostly, we keep ourselves in the dark about failure’s values, as well as the likelihood that it will happen.


Ah, yes. Failure. The F-Word of the new millennium. Click To Tweet


The sense of security that our plans give us is in direct relation to the level of fear we have that we will fail. We over-prepare to stave off any possible likelihood that things are unpredictable and that things might not go the way we need them to. That fear that paralyzes us, stalls us, is often managed by creating five year plans, projections, and the like.


You might have had a failure that truly changed the way in which you live, or affected you in ways that you are still living with today. Our actions do have repercussions. But very often, all that happened is that things didn’t work out the way we planned.


The way we hoped it would go doesn’t have the same amount of pressure. Also, when you hope for something you very often have many different solutions that work towards the thing you are hoping for. There is no final destination, no let down, no failure, because you were simply hoping.


Hoping and planning give us the same direction, but hoping only gives us half the regret. Hoping, in fact, leaves room for the unpredictable, it also allows you to make decisions that otherwise would’ve been impossible if everything you are doing rests on the foundations of a solid plan.


So if failure is the big fear, surely the way to go about it isn’t to pretend you are a fortune teller than can set a course for the next five years and know that it will work. The likelihood of your prediction being incorrect is high and your plan over that period only makes it most difficult to spot the changes happening around you that are getting in the way of your success.


When you are hoping you remain open. Every day is a new day, every season is a new season, and you can think short term to solve immediate problems in the best way. If you solve immediate problems, or preempt them (because you are able to be agile when you are hoping) and aim to create sustainable solutions – what do you need a five or ten year plan for?

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