The 6 ways to avoid over-optimistic planning and actually achieving your goals

There are numerous reasons why we don’t accomplish our goals.

In this piece, I’m not talking about lack of luck or money. Or the lack of thé brilliant plan or insight.

Bad planning can be a cause of misery in itself. It can cause a vicious cycle.

Bad planning leads to working too much, leading to bad self-care, leading to bad work, and thus working more just to stay afloat.

And, bad planning can drain your morale and thus hinder your progress.

Here are the 6 things that are most important to get right and often forgotten.

See it as an addition to last week’s Year Planning Canvas.

Perhaps I should write a small book about goal setting and planning or a manual for yearly reviews.

Onto better planning!

You overestimate what you can do in a year. But underestimate what you can do in a decade.”

1. Put the goal inside your circle of influence

We often put goals on things we would like to attain. Naturally.

But attaining these comes as an effect of doing work.

Making a plan is simply your best idea of what needs to happen to reach your goal.

The goal then needs to be translated to work you directly have influence over.

A bit mechanistically, but I often call this translating output to input.

2. Know what progress looks like

To stay motivated you need to know whether or not you’re making progress.

Doubt can creep in when you’re unclear what to do, or what now to do.

When translating your end goal to work that you need to do, make sure you’re very specific as to what that work exactly is.

This is hard to do well. If it was clear what you needed to do, there’s a good chance you’d have done it already.

But if you don’t, you’ll aim all over the place and doubt whether or not you should be doing it.

So, pick your best idea as to what the work is and commit to that!

Or, it can be that you haven’t divvied up the goal into smaller steps.

Translate a big year-goal into smaller goals for each sprint.

It’s easier to stay motivated if you have a (sub)goal within reach.

3. Build in previous commitments in your planning

We entrepreneurs are naturally optimistic in our ability to get things done.

When brainstorming it’s good to think in possibilities.

“If I cramp down, I can finish it in a week.”

But when you say that, you envision a completely empty week, right?

And, when you're planning, you need to add back in all the previous commitments, existing work, and areas of responsibility in your life.

Because these will require your attention and take time.

Your planning needs to include them.

4. Include the obstacles life throws your way

Another closely related one is being overly optimistic about what will go wrong or what life will throw your way.

You never expect getting ill, the death of a relative, or an important partner going out of business. But these things will happen.

Plan in the slack to be able to withstand these things.

5. Plan in touchpoints

The Pomodoro technique schedules your breaks and thus makes it clear the other time is not “break time”.

You should do the same with “doubt time”.

Your plan to achieve your goal is merely your best theory. It’s natural to doubt it before you’ve seen it working.

But, plan in touchpoints in the year. For example, at the beginning of every sprint period.

These are the moments you get to check whether or not you’re making progress and you get to revisit the plan.

The rest of the time, you don’t!

This helps heaps against procrastination.

You can note down observations, new ideas, and doubts. But you will continue with the plan.

(NB: At such a touch point you can also define “revisit events”: things that can happen that allow you to change course.)

By having this touch point date planned, your brain gets to relax.

And by not doubting, you’re free to do the work.

6. Put it in the calendar

Your urgent work will always get done.

But your goals are often forward-looking. There’s no one to make these urgent but you.

And your future self is a shitty negotiator.

Put important work in the calendar. Let the urgent work fill in around it.

Even better, do the important work first thing in the morning.

Imagine a few weeks of every day doing one important thing! The progress you’ll make!

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Of course, there is much more to entrepreneurship than planning. But planning well will get you farther.