Business Planning is an Act of Boldness, Vision, and Flexibility
I feel compelled to write this article has heard the following expressed by some entrepreneurs recently:
- Change and Unpredictability: “What is the point of business planning if things change anyway?”
- Flexibility & Iteration / Experimentation: “Isn’t it better to stay flexible with no plan and work on a short term basis based on what we know? Isn’t constant iteration a better alternative?”
- Pessimism: “Isn’t it a sign of pessimism to plan ahead and plan for challenges that we have no idea will really occur?”
- Over Optimistic: “Isn’t is a sign of being over optimistic and arrogant to plan ahead – after all how do we know what will happen in the future?”
It almost seems that to plan is considered to be ‘too British Army World War 1’ like – over-organized, archaic, rigid, and worse – a sign of impotence and incompetence.
My intention here is to address these concerns and to present a viable alternative to how planning could be done by most businesses today – an alternative that interestingly fulfills the following:
- Increase your ability to respond to change and unpredictability
- Maintain a plan that is flexible and not mired in unnecessary rigidity or chaos
- Maintain a plan that can include iteration and experimentation
- Planning that works regardless of whether you are being optimistic or pessimistic
- To step outside of the limitations of psychological assessment into boldness ‘with concrete direction’
Change and Unpredictability
This is a simple one to handle – imagine being a ship captain with no starting course or destination. Imagine the level of confidence that passengers would have in you if you were to say “We will take it day to day… I know where we are at today and let’s see as the day goes where we need to go next based on how the currents move or sway us.”
Now replace the ship captain with yourself if you are a business owner and your passengers with your customers, employees, vendors, and investors. Imagine their level of confidence in your leadership and stewardship.
On the other hand, if you did have a starting plan or course with milestones, you would have the ability to update your team and passengers fairly quickly in the event a storm or other challenges arise.
You want to create what the final destination looks like especially in dire, stormy, emergency-prone situations. This gives a place to anchor your brain – our brains need that vision to help organize thinking, strategy, and (yes) flexibility.
Captain Sullenberger, the great captain of US Airways Flight 1549 which ditched in the Hudson River and saved lives – created a quick, hasty but necessary vision “We are going to be in the Hudson”.
I would have refined it a little to say “We are going to be ON the Hudson”, but I honor the good captain too much to nitpick.
In times that are unpredictable and ever-changing, the more the need to create a vision that enables courage and guts to work in directed intention.
But in addition, I say – in times that are not that trying, one needs a set of initial milestones to start the course – to forge ahead first. Upon hitting obstacles, one must not shirk, but respond to the circumstances (short term response) as well as respond to the fulfillment of the vision or final objective (long term response).
This long-term response is done in the form of revising your milestones if need be to attain the vision in a realistic manner. Most people fail to review and refine the milestones leaving chaos and unfounded optimism or pessimism about the future.
NOTE: I am not creating any guarantees about this process – I am merely being a proponent for the realistic maintenance of the vision and goals.
Flexibility / Iteration and experiments
If you did indeed have milestones in place, the flexibility is in realistically assessing these milestones periodically (preferably often) to see if they need to be changed.
The worse thing to do for your brain is to set up unrealistic milestones or expectations. We know from the research of Professor Wolfram Schultz of Cambridge University – that when you fail to meet (unrealistic) expectations, your dopamine levels go down.
The opposite experience occurs when you meet (realistic) expectations. Dopamine controls your feelings of motivation and confidence – so I argue that without realistic milestones in place, you are left at the effect of your biology. What is the point of that?
However, planning can adapt to the need to try different experiments and iterations from time to time – as long as the discipline of seeing if the results of these iterations and experiments keep you on track to your final destination and final objectives.
This is critical in assessing if you want to try a particular iteration or a particular experiment – it has to make sense and it has to have a ‘stop loss’ when the final objective is put into jeopardy.
Over Optimistic (Arrogance / Hubris) or Pessimistic
People fear the arrogance associated with creating a vision and then working feverishly towards it. They fear it because they think that they may be taken off course from original values and objectives.
But if you think about it, the whole point of business planning (done right) is to head towards and stay on track for the fulfillment of your values and objectives – what you feel is right and good for your company, family, and the world.
As long as you stay clear-minded and specific about your milestones and the final objectives, you should have less fear about this.
I assert that this fear is really the fear of having to be accountable and fully in charge / responsible for the planning and fulfillment – especially when you put your behind on the line by declaring a bold vision or set of objectives. This is an understandable fear but should not be a fear to stop you from doing everything in your power to ensure success.
The last paragraph may be the crux of the situation – when we become honest with ourselves. Business planning is not that easy – but it is necessary if you are truly a vision-oriented leader. Planning is here to stay.
Let’s do this! If you’re ready to get started contact me or follow me on LinkedIn.

Since 1991, I’ve been reflecting on, designing, and implementing methodologies and systems for bringing a transcendent, creative and innovative approach to critical aspects of entrepreneurship.