Where goals fall short: a guide to wholehearted planning

Do you have something you absolutely love and hate about yourself?

I can think of a few things, but the one that creates a lot of dissonance for me is my tendency and ability to plan. It’s a blessing and a curse.

On the positive side, I can be relied upon to be as prepared as possible in any given situation. From packing for a family vacation, to coaching a client, or giving a keynote talk, you can bet your bottom dollar I will have done everything in my power to make sure it goes as well as possible.

Planning helps you to  make the best use of your resources of time, energy, money, and focus and create the best possible outcomes.

But the darker side of my planning can lead to being overly committed to a plan and trying to control people and situations to ensure things go according to the said plan. And you know, nothing good ever comes from that (just ask my husband and kids when I’m on a roll). No one likes being bossed around and told what to do.

Illustrator, Lisa Congdon refers to this tendency as “future tripping”, worrying about what could happen instead of being in the moment.

So, it would seem I have a bit of a conundrum on my hands: I like the comfort and sense of control that planning affords me, but I don’t want to miss the spontaneity of a moment or connection with a human I care about because I’m planning for the next one.

If 2020/2021 has taught me anything, it’s to embrace paradox i.e. the ability to hold competing thoughts or feelings at the same time and thrive anyway. Planning is a perfect example of how we can embrace paradox and THRIVE in our life and business.

If you’re interested in digging into this idea more, here are 3 actionable ways that planning can support you in life and business while you stay present to the people, experiences, and opportunities that lead to unexpected joy.

1) Reframe your relationship to goals and outcomes

Here’s the thing about traditional goals – they are something you don’t currently have, are linear, and exist in the future where you supposedly become “better” versions of yourself. Is it any wonder they often feel so restrictive and downright mean? What if we looked at goals the way fashion designer, Bethany Yellowtail does?  In Grace Bonney’s In the Company of Women, Bethany says:

“I don’t see success as a linear rise to money or fame, but rather as a full circle that leads me back home with the things I set out to accomplish.”

Option to investigate further: If Bethany’s approach appeals to you as much as it does to me, I invite you to consider the following question:  What accomplishment(s) would make me feel empowered, and proud, and that I’m living life on my own terms?

2) Get out of your head

I couldn’t help but chuckle at one of my favorite Instagram accounts @verybritishproblems because we’ve ALL been there!


When we ruminate about things we feel we should plan for but have done nothing about, the “problem” takes on greater proportions – from a bad night’s sleep all the way to catastrophizing about the state of the world and its imminent demise (or is that just me, LOL?). The answer: take action, seek answers and/or guidance, and you’ll likely realize it’s not nearly as bad or hard as you imagined.

For example, before we embarked on a full-gut kitchen renovation (still in progress, check out my Instagram stories for pics!), I was literally losing sleep over how we’d manage without a kitchen for 3 months. In these scenarios, all I saw was stress, mess, and bad food (which to be fair, isn’t far off the mark), but what is different is how I feel about it. The game changer? Googling “how to survive a kitchen renovation” after one such worry-filled night. A couple of blog posts later, I had a plan of how to set up a temporary kitchen and list of what I’d need and what I wouldn’t. Plan in hand, it’s been far easier than I could have ever imagined.

Option to investigate further: What problem(s) could you put within the context of a google question and take action on?

 3) Embrace the Stockdale Paradox

In the book, Good to Great, Jim Collins shares the story of Jim Stockdale, the highest-ranking United States military officer in the “Hanoi Hilton” prisoner-of-war camp in the Vietnam War. Stockdale shared how he survived torture and eight-year imprisonment:

“You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.”

When asked who didn’t make it out, he responded, “That’s easy, the optimists.” You see the folks who didn’t confront the brutal facts simply couldn’t survive the hardship.

I have tried and tested this method and it works. When I was making the decision about whether to close one of my businesses 8+ years ago, my husband poured me a glass of wine and said, “Let’s look at the brutal facts.” And we did. What would happen if I kept both businesses? What would happen if I closed one? Which one would I close? How would I get the remaining business up to speed to meet our income goals, etc? It was enormously helpful and not at all brutal. It freed me up to make the best possible decision and create a plan for it to succeed.

Option to investigate further:  What brutal facts are you avoiding? What are the questions you could ask that would elicit clear answers? Who could help you do this? (It’s easier with support!)

 If you’re a planner who’s looking to bring more humanity and less rigidity to the process or you’re not a planner but want to be more proactive and effective in your business and life, I invite you to join me on Dec. 20th at 1 p.m. for a FREE virtual workshop.  I will be hosting a Creative Mornings Field Trip called Create a Plan to Make 2022 Your Best Year Yet.  This one is going to be interactive and super fun, so bring paper, markers, and an open mind.

Are you ready to map out a flexible, human-centered, vision for 2022? Come join us. I can’t wait to see you there!

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