It’s Planning Season - Why Do I Feel So Lost? 

Has anyone else gone back to read their 2020 plans? 

If you’re like me, you did so with a dark sense of humor and a sense of foreboding that next year won’t be much different. 

That’s not to say I didn’t make progress toward my “big picture” or that I didn’t meet a single goal - dream - intention that I set for the year; moreover, it’s the fact that I abandoned my planner months ago and the idea of starting a fresh one feels…

pointless. 

This time last year, I was deep into planning season. I’d written my holiday bucket list and shared it; started packing for our company strategic planning weekend; outlined my year by month with dated launches, activities, and travel ideas. I wasn’t just planning, I was designing. 

Planning brings me joy, pleasure, and peace. I imagine the different areas of my life like Legos in one of those kits that are 3-in-1, but infinite. I can arrange what I have and who I am in any way and imagine the outcome. I watch a thousand movies in my mind while I plan. And, I live every single happy ending as it materializes on the page. 

Yet, after nearly a year of focusing solely on staying alive, protecting my career, and hunkering down, planning feels like a futile exercise. Why? 

Because I stopped. 

I stopped writing my daily list, other than for work. I stopped trying to read all the books in my reading list or do all the projects I set out to complete. Even with time and attention, I stopped listening to the plan. 

So, why plan at all if I’m just going to ignore my own directions? 

I bought my 2021 planner last night, the same one I bought last year and the most fitting “layout” in my six years of planning. I’m using the Target edition (i.e. less expensive) of the Day Designer. In the past, I’ve tried: 

  • Passion Planner - great structure but not enough “list” area, too focused on the visual time blocking with not enough space to process or take notes.

  • Ink + Volt - too small, rigid, and limited in all the areas where I want to work, yet I enjoyed the monthly prompts.

  • Bullet Journaling - simply put, I like lined pages.

I’m less an “end in mind” and more a “big picture first” kind of person, starting with the far-out ideals then zooming in on the day-to-day implementation. 

I also like specifics: planning for the holidays and for end-of-year gifting; seasonal shift lists and moodboards; specific “track” plans for the verticals in my life (career, finance, education, creative, home, health, hobby, personal development). These plans are fun to put together and truly enrich my quality of life. 

This part of me that feels like I shouldn’t plan for 2021 sounds so critical. She asks questions like, “What’s the point?” and “Why buy a planner you won’t use?” and even, “Who do you think you are to dream so big when the world is still in chaos?” 

And, worst of all, “What is there to dream of in all this? What is the point of looking forward if it’s likely to be swept away?” 

We have all lost so much, some more than others, and even on the precipice of a very big win (Biden/Harris 2020 thank GOD), it still feels like COVID and the national division in this country have cast an inescapable shadow over our future. 

There are plans I want to write: 

  • A holiday bucket list that spoils my friends and family and leaves me feeling refreshed and ready to take on a new year. 

  • A year ahead that sees me more healthy, happy, and progressive than the last. 

  • A complete vacation, one with places to stay that are not couches and no afternoons stealing away to the cafe to work. 

  • An educational journey that finally ends in a Bachelors in Business. 

  • Creative mini-sprints that see me back on my blog, nurturing a thriving garden (inside and out), collaborating with my friends, growing a business or two, exploring my passions, and participating in indie cinema projects around town. 

Even just spelling out the goal statements gives me butterflies. 

Now that I think about it, that’s enough for me. 

All this time I’ve been fretting about how I’ll get it all done. I’ve been holding myself to the standard that if I didn’t eat every single bite, I shouldn’t serve myself that huge slice of cake (with extra icing because it’s me). That if I didn’t use the planner every day or follow the carefully laid path or meet every goal, that all of it would be for naught. 

I was caught up in the outcome, when in fact, the journey is my favorite part. 

In fact, I love to plan. The plans don’t have to be mine — I spend a good portion of my work time planning: days, projects, launches, meetings; strategies, tactics, delegation. The moving of individual pieces into an arrangement that works sets me at ease and seems, when shared with others, to be helpful to others either directly or not. 

I think planning is often seen as a “best practice,” as part of a whole whether we like it or not. But, I enjoy planning as a standalone activity the way a choreographer designs a dance or the way an artist creates their artwork. 

The plan is the painting, the finished routine. 

All that’s left for me to do is dance. 


I’ve been building up a planning series you may find interesting or helpful in your own life design endeavors.

In the comments below, would you share with me your thoughts or reactions? Whether you’re a planner, a goal setter, a little disillusioned, or geared up for a new year?