Accomplishing big goals without over-planning

As a hyperactive planner, I really love making New Years resolutions. I’ve been making big goals since I was a teenager at home during winter break (and spring break, and summer break) — long lists of things I was going to accomplish, groundbreaking habits I was going to form. Of course, I rarely actually did any of them.

2015 was the first year I wrote lengthy, complex goals for myself that were grander than before. I accomplished more than I expected, but for the most part, I didn’t follow the plan. In this post, I want to deconstruct what I learned from a year of overzealous planning, and propose a different method for setting big goals.

Side note: during my previous long saga of goal failure, I was always at once too optimistic and too harsh with myself. All throughout college, I think I was weighed down by a feeling of inadequacy — not all that uncommon at my school, I imagine — and my self-value was predicated on accomplishing things, being better, being more, my language full of “should’s” and “need to’s.” Eventually, I realized that the rigid brand of self-improvement mentality I had was paralyzing, and ironically, to get anything done, I had to grow past that. But that is a whole other story.

Method: Deconstructing my life into parts

I followed a method similar to what Chris Guillebeau does: I divided up my life into 11 different areas. I reflected on each life area – what went well and what I wanted to work on – then I set actionable, bulleted goals and scheduled monthly check-ins.

Something that made a HUGE difference for me… I started using a Leuchtturm 1917 notebook to write yearly, monthly, and weekly reviews. It was an expensive notebook – the kind you’re almost afraid to write in. But that was the point. It made conducting reviews with myself feel almost sacred and ritualized. Or maybe it was mostly the tactile experience – the pleasure I got from the feeling of my black fountain pen touching the smooth cream archival paper. And drinking a cup of hot chai tea. Mmm…

Conducting a review of 2014

I started by going month by month and writing highlights, main things that happened, or that I felt. I scrolled through my photos to help jog my memory. Then, I listed my biggest challenges and what I was grateful for. I made a list of all my lessons learned from this year. I wrapped up the review section by writing one page about my year. There, I clarified my hope for 2015: to feel like I had embodied myself. To get grounded in myself.

Making goals for 11 areas of my life

I broke my life, like a pie, into as many pieces as I could think of: Self-growth, Home, Finances, Writing, Creative Projects, Learning, Professional, Tango, New York City, Travels, Family, Relationship with J, Friends. I tried to be comprehensive. For each section, I reflected on the previous year – things that went well and major challenges. I analyzed those challenges and thought about systems that could address them. Then I made my goals for 2015 and finished with specific, actionable to-dos.

Here’s an example of what one section looked like. Creative Projects:

Creative Projects: My big goal was that I wanted to create beautiful work that I was proud of, and had an impact on people.

My sub-goals were:
1) Decide on a creative project by conducting monthly planning of project “chunks.” Assign myself specific weekly steps. Allow myself commitments of 1 month, 2 months, or 3 months per project, with a quota of 4–8 hours/week.
2) Keep on-going project notebooks with articulated vision, repository of ideas, and inspiring content
3) Do review at the end of each project chunk.
4) Fill time quota from projects. January, for example: Blog / 2 hrs. Storyfund writing and publishing stories / 3 hrs.

Results: Nothing went according to plan

So… that didn’t really work. None of that planning actually happened. Instead, I achieved my big goal for the area (create beautiful work with impact) in ways I would’ve never guessed: I decided to take an evening class at School of Visual Arts. I took on a freelance client. Then I decided to quit my job and start my own creative business. I far exceeded my goals for Creative Projects, and my original resolutions had become irrelevant. A similar thing happened with my goals for 7 other areas.

But in one key area — self-growth — my goals were predominantly focused on forming habits. I followed that plan, and quickly it formed the foundation for pursuing goals in all other areas of my life. In the words of Tiago Forte, whose habit formation course I took on Skillshare, starting with just one habit is the spark in a gas-filled oven. For me, habits changed everything this year.

Conclusion: What I’ve learned about accomplishing big goals

Don’t get too granular too fast. I over-planned, so I ditched (most) of the plan! I tried too hard to be comprehensive and specific. My bulleted action items became irrelevant over time and across changing contexts; in other words, I was bad at predicting my future self. I was trying to impose a system or a structure onto parts of my life that resisted structure, or weren’t clearly defined enough to have one.

Use momentum, not to-do lists. Despite basically ignoring my plan, I accomplished a good 70% of my goals. None of what I did mapped onto my original action items, but it comes from the same momentum; momentum I’ve always had but never knew how to use. I’ve come to realize that when your life is driven by momentum, your urge to do feels effortless and energetic — like swinging on a swing set. It is the opposite of crossing items off a long to-do list, failing, and feeling very guilty.

When possible, translate goals into routines and habits: My biggest accomplishment this year is probably building a morning routine that has served as my essential nourishment for my life, and is the core foundation for everything that I do. Along with momentum, habits are far more powerful than to-do lists or goals, because once they’re set, you don’t expend any mental energy on them. It declutters your mind, scaffolds your day, and gives you the energy to focus on what matters.

Focus on intentions behind the goal. It doesn’t matter that I met nearly none of my specific goals. More important is that I’ve met my intention to get grounded in myself. Having a guiding word or intention for the year helps you pare your life down to what’s essential. It captures the essence of your goal – your driving force behind the goal, and how you want to feel as a result of this goal. And even if specifics change, the intention stays the same.

Make the goal simple and focused. I think I’m pretty bad at simplicity. I love overcomplicating things. The One Thing is a book that shaped my understanding of goals more than anything else I’ve read this year. Instead of trying to micromanage all aspects of my life, I just needed to keep it simple. Focus on less, on one thing, and the rest will fall into place. Focus comes from truly understanding what I want, and why I want it. Mainly: how does it help me reach my intentions?

My resolutions for 2016

I’m exhilarated thinking about 2016. I have two guiding intentions / words. (Hopefully two isn’t too much.)

Flow and Gentle Growth.

By flow I’m referring to using the magic of momentum, and trusting in the process, rather than rigidly obsessing over the outcome.

By gentle growth, I mean: always finding new ways to grow and improve – in business, art, life, relationships – but doing so with an attitude of ease and flexibility.

My mother always used to tell me: be less like a rock, and more like water. You think you are strong, but really, the water will wear you down.

This year, instead of breaking my life down into 11 areas with 3-5 things per area, I just have 3 goals, or intentions, if you will.

Build a business that feeds my soul and is financially sustainable.
Cultivate my quality of mind through mindfulness.
Direct and optimize my energy, attention, and effort.

Hopefully, my brain can focus on 3 things easier than it can on 40. Once upon a time, I believed in the NO PAIN OR NO GAIN mantra. This time around, I’ll remind myself: accomplishing goals doesn’t have to be painful or strenuous. Not anymore. It can feel natural, too. It can feel inspired.