The art of long-term planning

Ten insights into my process of strategizing for the year(s) ahead

Nov 29, 2023

Hello from yet another Amtrak train. I’m writing this Tuesday night as I head to New York to speak at a conference on elections and everything we should be worried about. You can be sure I’ll be pulling out my panic responsibly line (which, if you missed it, the merch store is now up and running!).

A huge hello to my new subscribers, and thank you to my existing ones who were so gracious to share my post earlier this week when I was just short of hitting 5,000 subscribers. I’ve now blown past that goal and am so grateful.

A quick heads up before I get into this week’s newsletter. About five minutes after I finished this Meta announced their plans around the 2024 elections. More to come on all of that because there is a lot buried in this fact sheet.

That brings me to today’s topic - planning. I did a poll on LinkedIn a few days ago to see what folks would be interested in from me. The first was a guide to next year’s elections, and the second was learning more about how I think about long-term planning.

I’m going to do these in reverse because the guide is going to take me a little bit to put together.

AI created image through Midjourney of a woman with chin-length blonde hair sitting at a desk and doing long-term planning while looking at calendars for the next few years.

While planning for me is a year-round thing, I like to take some days around December or January to get away from the day-to-day chaos, take stock of everything, and start brainstorming about what I want to do. This includes personal and work. I usually take a day or two in Summer as well to do a check-in and make any adjustments.

What follows is a bit of my process. It’s not the same every year, and you should really adapt things to what works for you. I’d love to hear in the comments any tips and tricks you have for doing stuff like this!

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Set aside dedicated time: I find that ideas come to me at all sorts of times, so I try to do this in chunks - for instance, I took three days here after Thanksgiving and have set aside time right before I go home for Christmas and that first week of January. But it’s key for me to go somewhere that’s not my home, is surrounded by nature, but has internet.
Have a process for collecting ideas: While dedicated time is important, ideas come to me at different times. This is why I don’t try to do it all in one retreat. I might be sitting down for a dedicated brainstorm, or I could be driving or out with friends. I keep a Google doc for jotting down ideas quickly. Sometimes, I email them to myself to be added to the doc. Regardless, ensure you have a way of writing things when they come to you, as you’ll forget otherwise.
Start with a retrospective. I don’t think enough people - me included - do enough to take stock of both what we’ve accomplished over the last year or years as well as how much the world has changed. Tomorrow - November 30 - is the one-year anniversary of OpenAI releasing ChatGPT. One year ago. So much has changed. In a few months, it will be four years since the pandemic started. It’s important to see where we’ve come from to celebrate our wins and identify themes. Sometimes, I go even further back in history to see what it can teach us. But set a time frame of how far you want to return and take stock of what you’ve accomplished and fell short of. Don’t focus just on what you fell short of. Take some actual time to celebrate what you’ve done. Once I’ve created that list, I like to open a bottle of champagne to drink while reading it.
Set your look-ahead mile markers. Next, you’ll want to think about the mile markers you want to use when looking ahead. If you are a person who likes templates, you can see the ones I would offer my team at Facebook when doing career planning. Some years, I’m really only looking one to two years ahead. In 2020, I looked to 2024 because I knew every five years, there would be a lot of elections - which led me to have a rough four-year plan of what I wanted to work on. Now that that year is almost here, I’m starting to think about not only what I want to accomplish next year but also what 2025 might look like as well as through 2030. Do what feels right to you - just know that the further out you go, the more likely it is you’ll need to pivot because the world changes.
Think about personal and professional. This is going to be another one of personal preference. I like doing these together as it’s all intermingled for me. Others might want to keep them totally separate. The important thing, though, is to have some of both.
Not all your goals need to be big, hairy, audacious goals. You’ll want a mix of the types of goals you set. One goal I had for myself this year personally was to have a better skincare routine. Next year, I’m thinking about trying to go for at least a short walk every day. I recently listened to Bill Simmons on the Smartless podcast, and he talked about how every year, he wanted to try to hit something new out of the park, like starting a podcast or another year being on live TV. I like to try to visit a new country I haven’t been to every year, and I’m thinking about doing a writing retreat either at
Kate Hill
’s place in France or I met Kristi Leonard on Threads this week, who has a beautiful place in the Blue Ridge mountains. (PS: If you haven’t read Main Character Energy by
Jamie Varon
yet I highly recommend it. Great reading for the holiday break.)
It’s ok if you don’t know what you want and/or you have a lot of ideas of what you might want. This is exactly where I find myself right now. I’ve got some potential options for the future of my consulting business. I love writing this newsletter and producing the podcast. I’m excited to try building passive revenue with stuff like the Panic Responsibly merch store. I’ve thought I might try building out a media company that focuses on elevating voices in tech and democracy worldwide. I haven’t closed the door on returning to a company someday, but I also really like my independence. I think this is ok. I joke that I’m playing Goldilocks to see what fits and what doesn’t. I don’t have to do everything simultaneously (though I sure try!). Where I’m at right now is the information-gathering phase. By doing the retrospective, I can think about what I’ve enjoyed versus what I haven’t and what new experiences I might want to get in the future. Today, I was just talking to my financial advisor, and down the road, I’d like to learn more about what it is like to pitch and work with investors (I’m sure some of you are screaming at me to avoid that at all costs). The fun part about brainstorming is that no idea is stupid, and it’s great to get it all down to sit on it for a while.
Determine how you best like to visualize/organize things. Ok, you’ve got all these ideas, retrospectives, etc. How do you organize it? As many of you know, I love a good wall with Post-its. I also love doing a good grid for everything from which coffee maker to buy to evaluating all my options against a set of criteria. I LOVE mind maps. Others prefer prose, some like good ol’ outlines. Whatever your favorite tools are, think about the best way for you to start organizing your thoughts. I like doing these on those big sheets of paper you can stick to the wall, so I see it daily.
Metrics are nice, but not the only thing. I love it when the universe sends me a message I didn’t know I needed. Yesterday, that came in the form of this post by
Amanda B. Hinton
about how she’s moved away from metrics to a “felt sense of satisfaction.” I like a mix of the two. Last year, I definitely thought that it would be nice if I could hit 5,000 subscribers by the end of the year (thanks again!). But I wasn’t overly obsessed by it. I track the money I bring in to make sure to pay my bills and live the life I want to, but I don’t have goals of how much more I want to bring in year after year. Heck, this year, I cut back on how much I was bringing in because I didn’t like how I was spending all my time in meetings. This year, I spent a lot more time on things I wasn’t paid for in hopes that it would bring business down the line. Am I totally happy? No. But do I feel pretty good about where I’m at? Yes.
Try not to stress too much about it. I know, I know. This is easier said than done. But for me, planning is an ongoing process. This summer, I spent a lot of time thinking about what the next 18 months might look like. I’m now considering the next few months and the next few years. I’m also prepared for the unexpected phone call or email with an opportunity I never considered. For me, it’s important to plan and be okay with pivoting and throwing it all out. In the end, it all usually works out for the best.

If you were hoping for an overly prescriptive answer, I’m sorry! But I really don’t think those work because we’re all so unique in how we like to do this work. I adjust and adapt all the time. But hopefully, this might be a little inspiration for you to start doing that retrospective and planning before we hit the new year. If you want, share yours in the comments so we can learn and celebrate with you!

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