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Is Your Systematic Nature Preventing Your Success?

The pitfalls of over-planning and how to avert them.

Kate Jones
May 19, 2017 · 11 min read
Image Credit: Unsplash

We all know the drill when it comes to achieving great things: Create a captivating vision, build a rock-solid plan, and execute with vigor.

This timeworn wisdom is perpetuated throughout educational establishments, strategic management literature, and corporate businesses the world over.

The detail-oriented among us are praised and rewarded for our superior ability to produce comprehensive plans. And we worship these handsome, labyrinthine documents, perpetuating the belief that the plan is paramount.

So why do we so often fail to achieve our biggest goals?

Problems arise when we over-plan — when we narrow our field of vision to such an extent that we trap ourselves into a corner. Blinkered by our plan, the smallest of obstacles overwhelms our mission. We fail to spot the opportunities to pivot and progress.

In business, Agile and Lean methodologies beat back this flaw of traditional waterfall techniques. Even then, teams can find themselves stuck. This is especially true of conventional corporate business where transformational change can become trapped in a bureaucratic web.

For example, in the 2015 Annual State of Agile Report, two of the top 5 causes of Agile failure were related to company culture. When push comes to shove, the red tape still often wins out and the contemporary processes are manipulated back to the old ways: importance given to the plan rather than the actual outcome.

When the job of planning becomes regarded as an end in itself — instead of simply a prescription for future action — we lose all sense of perspective.

Planning and ‘The Thing.’

We can make this same mistake in life.

Typically, we set out on a path to achieve ‘The Thing’ — for example, a particular job role we aspire to or a small business we intend to launch.

In an attempt to accomplish ‘The Thing,’ we label it, create a vision, and set SMART goals. We put in place a milestone plan — to achieve the ‘Big Thing,’ we must achieve several ‘Small Things’ at periodic intervals.

At some point along the way, one of the ‘Small Things’ proves elusive. This “Small Thing” becomes a monumental boulder unceremoniously dumped into our path, and we fail to find a way around it.

This type of scenario is a symptom of over-planning and over-niching. It comes from creating roadmaps that are so specific and rigid that the likelihood of us bringing the trip to fruition is almost zero.

Finding an effective way to sidestep the pitfalls of over-planning first requires that we understand the problem itself.

And that starts with imagination.

The problem with imagination.

Whether we realize it or not, we are all experts at imagining.

When we think about what we might have for dinner, or what we need to do at work tomorrow, we are imagining — projecting an image of the future based on our current knowledge.

Forward planning relies on this skill—an ability to predict our future state in an accurate, objective, and timely manner.

But life doesn’t occur in a linear fashion. And despite what we might like to think, our species is pretty terrible at unbiased forecasting.

In particular, evidence shows that our expectations of the future typically far exceed the eventual outcome.

In one example cited by neuroscientist Tali Sharot in this 2012 Ted Talk, 0 percent of married people predicted that they would divorce. This confidence flies in the face of the fact that, in the Western world, approximately 4 in 10 marriages end in a split.

We have the same bias about our selves: Studies show that we believe that we are more likely than our peers to succeed. And that most of us think we are more attractive, more personable, and more interesting than average.

What we are talking about here is optimism bias. And the problem with this notion is that — statistically — we are setting ourselves up for failure.

However, it’s not all bad news. Indeed, modest optimism allows us many distinct advantages. As Harvard Lecturer Shawn Achor discusses in his book The Happiness Advantage, there is evidence to show that optimism, in fact, increases our likelihood of success. Studies show that optimists tend to set more goals, put more effort into achieving them, stay engaged in the face of challenges, and overcome obstacles more easily.

The problem comes when optimism causes us to grossly overestimate our current abilities.

From a planning perspective, when we are in a dysfunctional state of optimism, the chances are that reality will not be able to match up to expectation for long.

This is especially true when we’ve woven those threads of over-optimism in an intricate, acutely-detailed vision of our intended future. And that’s easy to do when we are full of anticipation.

The problem with anticipation.

“Plans are nothing. Planning is everything.” — General Dwight D. Eisenhower

Evidence suggest that we enjoy the process of planning more than the actual execution of our goals.

One study from the Applied Research Quality Life Journal (2010) showed that participants’ levels of reported happiness were higher in the days and weeks leading up to a vacation compared with levels reported both during and after the vacation.

In other words, the time we spend planning and thinking about an event can make us happier than the actual event itself.

This is particularly true when we are planning something that we expect to be a joyful experience — such as achieving our greatest ambition.

The joy that we get from planning our success can be good for us and our sense of well-being. But it can be a disadvantage in our ability to plan effectively.

The feeling of joy and comfort that we receive from planning often hides a deeper emotion — one based in the fear of failure. The planning itself gives us a misleading — yet deeply desired — sense of control.

In his book Stumbling On Happiness, Harvard Professor Dan Gilbert points out that we find it gratifying to exercise control — and not only because of the service this proffers our future self. We experience immense enjoyment during the process of exercising control.

The more we plan, the more we feel in control. The more we feel in control, the less anxiety we experience.

The longer we can get away with staying in planning mode, the longer we can extend this comforting feeling of control and avoid the inevitable onslaught of the unknown.

In this post, Dr Tim Pychyl explains how even the most rational types of delay (including planning) can manifest as procrastination — in other words, planning becomes and activity of avoiding the facing of an aversive task right now.

To compound this, when we use planning as an avoidance technique, we are also mapping out our future unreality in the most graphic of detail. We are setting ourselves up for certain failure.

Problems arise when we mistake our feeling of control with the supposition that we are actually in control. And these problems escalate when we over-plan.

When reality bites.

When the inevitable occurs and reality fails to live up to our carefully constructed plan, it leaves us bewildered.

The shock of being wrong puts us off-balance. That all-important sense of control is swept out from under us, and we find it almost impossible to see a way forward.

This predictably leads to one of the following reactions:

None of these reactions are helpful to our progress. But they’re quite understandable — when we are faced with an immovable, colossal boulder that threatens to unhinge everything that we’ve worked towards, it’s no wonder we crack.

But what if there was a way to see beyond the rock?

Widening our field of vision.

With the traditional approach to planning — especially if we fall victim to over-planning and over-niching — our vision is fixed and resolute. When a boulder lands in our path, the margin to skirt around it looks extremely narrow.

We need a method to widen our field of vision without losing touch with our destination (‘The Thing’).

In order to achieve this, we need a more flexible approach—a framework for success.

This starts with an analysis of the true intent behind ‘The Thing.’ We must discover what lies at the core of our ambition to arrive at our desired destination.

We humans like to label things. Ourselves (“my name is…..”), our purpose (“I am a…..”), and just about anything else we can get a hold of. So when we decide to achieve something, the first thing we do is label it (vision statement) and make it SMART (goals to achieve the vision).

In fact, we are actively encouraged to do this by using planning systems.

Take my situation as an example. When I was building my coaching business, my vision statement (label) could have looked something like this:

To become a successful freelance coach.

My definition of success with that could have simply been: a) number of clients recruited, b) retention rate, c) hourly rate achieved.

But those don’t really describe what I was after. I wanted to avoid the pitfalls of affixing a rigid label to my desired destination, so I used a different framework.

I took a look under the hood to understand what was driving my desire to become a freelance coach. I achieved this by looking through two lenses.

The first was to understand my innermost values. What do I advocate? How do I choose to behave?

I discovered that I fundamentally stand for the values of empathy, betterment, and depth. I find this exercise from Mind Tools a helpful aid for identifying core values like this.

Secondly, I pinpointed the needs that drive my happiness. What experiences do I need to encounter on a daily basis? What is the work that lights me up?

Using Tony Robbin’s Human Needs Theory, I recognized that my strongest needs are those of variety and contribution. More specifically, I found that the foundational needs which bring me happiness are freedom to work to my own schedule and work that’s focused on personal development.

By bringing together my core values and my foundational needs — and framing them as a decision-making tool — I built my personal success framework:

I will consider all opportunities that align with my values (empathy, betterment, depth) and meet my personal needs (freedom to work to my own schedule, work that’s focused on personal development).

By modifying the initial label into a wider statement of intent, I increased my field of vision. I made it so I’m capable of pivoting or detouring when boulders are placed in my path or (maybe more importantly) when alternative opportunities are presented to me.

By avoiding the temptation to over-imagine, over-plan, and over-niche, I’ve given myself the chance to succeed more broadly and more frequently.

How this works in reality.

I’ve used this exercise with many clients in the past and the results repeatedly astound me.

A recent example was a client who bounced from large multinational to large multinational, clawing his way up the ladder. His ambition was to become Head of Sales for a UK division.

He sacrificed a lot along the way, including time away from his family.

But he reached a boulder — a certain layer in the management structure — and could not find a way to push through. Interview after interview came and went, but found rejection waiting at the end of the process each and every time.

This bothered him immensely, until one day I asked him why he wanted to become Head of Sales.

The questioned flummoxed him. “Well, it’s obvious. Because it’s the only path — the route to success.”

But why? Why was this the path for him? “Because I’m a great salesperson and a great leader.”

And why else? “Because I like helping people to succeed.”

And why else? “Because I’ll make more money.”

And why is that important? “I don’t know really… it’s what I’ve always believed.”

We dug a bit deeper and discovered his needs were significance and certainty. And his values included social equality, nurturance, and education.

I probed further: “Why is becoming Head of Sales the only path to achieving this? In fact, how well does it align with your values?”

That was the lightbulb moment.

Over time he realized that he’d been chasing the wrong dream. And even worse, it was an incredibly narrow dream — one that he was subconsciously sabotaging because it didn’t fit with his values.

Fast forward a year, and he’s part way through a counseling degree, working in a role that excites him, and he’s feeling happier than ever.

He widened his field of vision, discovered new opportunities and pivoted.

What you are reading right now is another very apt example of this more flexible approach to success.

If I had stuck to a rigid vision where coaching was my only available path, I would not be sitting here writing this article.

I would have missed out on an opportunity to work on a project where empathy, connection, and betterment are the core themes, and my needs of working to my own schedule and focusing on personal development are met.

Too much of a good thing.

With this approach comes flexibility and latitude, which is a good thing. But unless we frame this approach with a clear, unshakeable set of values and needs, we can lose focus.

If our framework is too loose, we have no way to analyze opportunities and take decisive action, which can be just as bad as over-planning.

The key is to find the sweet spot between flexibility and rigidity. You develop this over time with practice and consciousness.

Open yourself up to a world of relevant opportunity.

We’ve learned that planning in itself is no bad thing. The exercise of planning — the imagining, the hoping, the dreaming — is not only useful but beneficial to our wellbeing.

Problems arise when we abuse our ability to plan — when the plan itself becomes the outcome, rather than our real ambition for increased happiness and success.

Don’t be fooled into over-niching ‘The Thing’ and over-planning. Instead, consider each and every opportunity that aligns to your needs and values — even if they’re not part of your plan.

And remember to step back from the plan for that wider view.

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

Kate Jones

Written by

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

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