Mapping Out My Next Chapter

A look at how I’m thinking about the next five years

Four years ago, at the Ritz Carlton bar in Washington, DC, I sat down after meeting with a mentor of mine to start mapping out what I might want the next five years of my career to look like. It’s when I first realized how big of an election year this year would be. It’s how I eventually decided to take the leap to leave Facebook and start Anchor Change. I covered that process in this post.

In the weeks leading up to the holidays and as we slowly work our way into the new year, I’ve been reading a lot of great newsletters and posts by people about how they like to do their planning. I wrote one myself with the ten steps I take when approaching this.

Last week was slower for me as I ramped down some work and geared up to start at Duco. I found myself staring at my original mind map that I shared on Sunday and realized I had done many things I set out to do. I mean, hell, if I can brag for a hot second the New York Times cites my and Ana’s research into the number of elections happening this year. Not bad for only three years into building the company.

So, I’m doing the process again. I’m updating it to think about the next five years - which would take us through the 2028 elections and just before the next big wave in 2029 (though not as big as this year). I thought that I would share some of how I’m thinking about my goals, both professionally and personally.

I’m also starting to plan out the content calendar for the newsletter and the podcast for 2024. One subject I want to tackle is looking at common narratives around how technology companies approach elections and content moderation in general, what those narratives get right, and what they might be missing.

I’m also starting to think about different formats I might explore, such as videos, short audio clips, chats, and more. To start experimenting with those, I am going to do a chat on Thursday at 10 am Eastern, where I’ll solicit ideas of the narratives people would like me to explore in my next newsletter.

I’ve also been doing a lot of calls lately with folks wondering how I structured my consulting business. Would you be interested in a post about my lessons in becoming a tech consultant and building my personal brand? Vote below.

Please support the curation and analysis I’m doing with this newsletter. As a paid subscriber, you make it possible for me to bring you in-depth analyses of the most pressing issues in tech and politics.

What the hell do I want to do in the next five years? Who do I want to be? What life do I want to have? How do I want to feel?

Those are just some of the questions that have been rattling around in my brain for the last month. 

I talked on Sunday briefly about how much Glennon Doyle’s book Untamed helped me in 2020. I picked up the companion journal and started flipping through it late last week. I’ve been journaling and/or thinking about some of the questions posed in it, such as:

1. How much of my time is spent feeding my soul versus playing my various roles?

2. What do I want more than anything in the world?

3. What feelings are most difficult for me to feel or express?

4. What boundaries do I need to set?

5. When you are still and listen to your intuition/knowing, what does it say?

I’ve been going through the book again and realized something - I’m thinking about the answers to her questions and reacting to her stories differently than I did four years ago. I’m not the same person I was then - I’ve definitely grown. 

For one, I trust my gut - or, as Doyle and

Elizabeth Gilbert

call it my knowing - way more than I did four years ago. Much of this is thanks to the help of Rebecca Auman and some of my digging into spiritual practices. I also tried writing myself a letter from Love for the first time - this is Gilbert’s Substack - and it was a beautiful experience. I’ve been following her newsletter since it started, but there was something about doing all this reflecting and feeling that compelled me to do my own finally.

PS: It’s worth listening to Gilbert’s interview on Doyle’s podcast, We Can Do Hard Things. I enjoyed it.

When writing that letter I thought a lot about the piece I did in 2022 about Reclaiming the Fairy Tale, which were thoughts about being a single woman in her 40s. I’ve learned so much since then, but I still struggle with many things I mentioned there.

This is all to say that journaling and writing are a huge part of my process. 

Three other things have been helpful:

1. Sticking with mind mapping as my tool to organize my thoughts. I don’t think in linear outlines and this is so much easier for me to get things out of my head and onto paper.

2. I can’t remember who said this for me to give proper credit, but one of the things I read in December was about how someone likes to list ten things they want to do in the next five years. I came up with five really easily, but the last five have been HARD. It’s also been really challenging for me to think about non-career goals to include, but I’m forcing myself to do so.

3. Rebecca suggested pulling a tarot card for each “arm” better to understand each theme's energy/opportunities/challenges. I did that and also pulled an animal spirit card for each. I love what I got for each of them.

Here’s my mind map as it stands now. You’ll see I’m sticking with my four main pillars: mentor, voice, build, and personal. 

1. I’m going to add edge walker to the trailblazer label. Rebecca called me this in the description of the podcast we did together, and I love how it describes what I try to do.

2. I think I will expand the mentor pillar to be mentor/convene, as I’m really excited to continue doing the dinners and happy hours I started last year. 

3. You can see by the voice pillar that I still have A LOT I want to say, including finally getting my TV show/book series Tired of the Grind out to the world.

4. The build arm is probably my most pie-in-the-sky thinking. I won’t necessarily do all of these, but they are more things I’m interested in. The media company idea is me trying to think how I can help amplify more voices from the trust and safety field.

5. I built the personal arm a lot more than I did in 2020. In 2020, I had one goal: spending more time with my friends and family. This time, I have more goals for where to live and travel. I also want to continue to deepen my spirituality practice and start a regular walking routine. 

If you are interested, here are the card pulls for each. The middle ones are for the mind map overall, and then the rest correspond with each arm of the mind map.

For those unfamiliar with tarot or Kim Krans’ animal spirit deck, here’s briefly what I took away from each of these.

• First, having pentacles down my plan's center, the core, tells me I will be successful. I must make it happen, but it’s a nice sign.

• Trailblazer (Ace of Pentacles, Golden Egg) - I’m starting a new chapter and need to lead from my intuition/what I really want.

• Themes (Nine of Pentacles, Nightingale) - These focus areas are my happy place and where my voice can have the most impact.

• Home (Eight of Pentacles, Bat) - I’m mastering my craft and am transitioning where I do it from (aka the new job!).

• Mentor/Convene (Death, Octopus) - I need to change how I do this and set boundaries.

• Voice (Ace of Wands, Dragon) - I should be creative and stay true to myself in what I say.

• Build (Hermit, Whale) - I need to look inside more and dive deeper to understand better what I should build that will have the impact I want.

• Personal (The Fool, Cobra) - I’m at the start of a new journey for myself personally, and I should listen to my inner teacher and other guides to help me.

I’ve still got some work to do on this. For me, this is not a process to be rushed but rather thought through over the course of weeks. I find sharing it with people and discussing it helps me through that.

I also wanted to share where I’m at in case it does help some of you who might be going through similar exercises. Writing it down also helps me to continue to think through it. I’m debating if I do a vision board as well. I think I might.

I would be curious to hear about others’ processes and tools they use for this kind of planning. Please share in the comments because I know what works for everyone is very personalized, and we can all learn from one another.

Please support the curation and analysis I’m doing with this newsletter. As a paid subscriber, you make it possible for me to bring you in-depth analyses of the most pressing issues in tech and politics.