• Ariana Friedlander

Imaginative play & planning

"Now let's pretend you made me a bathing suit with purple flowers." My daughter instructs me as I play with her.

At different points, I think I get what she's doing and interject my own idea only to be corrected, "No, let's pretend..." she redirects me each time, which feels a bit frustrating.

But for a brief moment, I recall being a kid - my imagination was a place of safety and comfort that I often sought solace in. My daughter is no different, during the pandemic her imagination has been a place where she has complete control despite her world being turned upside-down.

I think how wonderful it is for her to be able to create an entire world in which she plays in the blink of an eye.

As I continue to let her dictate the terms of our play I see another side that I relate to painfully.

In the land of our imaginations, everything always works out exactly the way we want. And if we stay only in that place, we become detached from reality. Now, that might seem obvious but stay with me a moment.

Imagination and visioning are close cousins. And anyone that willingly steps into uncharted territory does so with an idea in mind and a belief that their vision will become real. It is essential for leaders and entrepreneurs to actively imagine their future.

The problem occurs when we mistake imagining how we will turn that vision into reality as a bygone conclusion. Reality offers a tension that propels ideas forward or stops them dead in their tracks depending on our ability to dance with it.

In the early days of my business, I imagined what I wanted to create, then I thought through a precise plan for how I'd make it happen. That was the exciting and easy part. Sometimes I would make it quite a way into execution, believing my idea was going according to plan before everything crashed and burned - an outcome that could have been avoided had I reality checked my expectations and iterated.

A few years ago my daughter came up with an elaborate plan that would allow her to play with the characters from her favorite TV show. It involved cutting a hole into our TV so they could come into our house or she could go into their world. As she described this plan to me before bedtime one night (it really was rather elaborate) she beamed with excitement and pride.

I didn't have the heart to tell her it wasn't going to work. She woke up the next morning looking for something to cut a hole into our TV with. She was rather distraught when I informed her we were not going to execute her plan and why.

A well-thought-out, elaborate plan is no guarantee of success and yet we can't completely wing it. We can't stay in the land of fairies, unicorns and Santa Clause forever. Make-believe is great, but there are no boundaries there, heck, there's not even gravity unless you want there to be.

Real-life has boundaries. As a misfit, I like to push on boundaries that don't make sense, such as "we've always done it this way." Or, "it's business, not personal." Or, "it can't be done because we tried it before and it didn't work." Those are self-imposed limits and breaking them is essential if you want to innovate and create positive change in the world.

But there are other boundaries I must adhere to in order to succeed. For example, fitting what I offer to a market need or killing an idea that has no market ASAP because hugs don't pay my mortgage.

At some point, we must reality test our ideas if we truly want them to come to fruition. We must introduce our plan to the world as a guess, like placing a formed yet still supple piece of molding clay down and letting others inform the final shape it takes.

Peter Drucker says in The Five Most Important Questions You Will Ever Ask About Your Organization, "Planning is not an event. It is a continuous process of strengthening what works and abandoning what does not, of making risk-taking decisions with the greatest knowledge of their potential effect, of setting objectives, appraising performance and results through systematic feedback and making ongoing adjustments as conditions change."

A lot of leaders fail at ensuring that planning is a continuous process. They invest in a retreat, create an extensive plan that they have designed, printed, bound, and widely distributed, then everyone goes about their business. The plan ends up being an expensive dust collector.

So how does one turn planning into a continuous process? It's important to give yourself the time and space to reflect on where you've been, envision the future, and identify steps for getting there. But what you craft must become a living and breathing document. In order for that to happen, you need to incorporate long-term plans into daily, weekly and monthly practices for managing your productivity.


There are lots of resources that enable you to link vision with goals and tasks. The trick is finding the one you will actually use to continually close the feedback loop that allows for adjusting as conditions change (which they inevitably will, thanks 2020 for making that abundantly clear).

My go-to tool for ensuring my plans stay alive is my journals. Clients have agreed that learning these journaling techniques has led to their success both personally and professionally.

Ben West, gave an unprovoked ringing endorsement for the planning techniques I teach at a Journal Jam earlier this year, "I was just gonna say how strenuously I endorse this...because of how instrumental it has been to my personal success and the success of my enterprise."

There isn't one right tool for planning, there's the best one for you. Now that we are halfway through this year, it's important to take a step back and evaluate how your plans are measuring up. Are you still trying to cut a hole in your TV (proverbially speaking of course)? Have you forsaken your goals for 2021 because of the tyranny of the urgent? Or are you confidently on track, turning your goals for 2021 into reality?

Join us for a special Journal Jam this Thursday where we will do a Midyear Review. You’ll walk away with greater clarity and tangible actions to turn your goals into reality and make 2021 everything 2020 was not. More information and registration is available online here.

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