What Will I Do Next?

Many paths, few answers.

Photo by Victor on Unsplash

I’ve been thinking about the lyrics from the song “Road” by Lane 8.

It goes…

I’ve been staring at a road,

Too scared to follow up.

Even as the sunset descends on me,

I stay unmoved to change the view,

Of where it leads.

It captures the feeling of unknowing that I’ve been experiencing. You know there are answers down the road, but you’re afraid to take the wrong turn and so you stay still, feet planted. Until you get some motion to change the view, you’ll never know what lies ahead.

I’ve spent the last four months on sabbatical, standing still on the question of what I wanted to do when I returned. Which made it suuuuper fun when I went to CMX Summit last week and everyone asked me the same question, “So what are you going to do next?” (CMX was awesome btw, I’ll write about that soon).

This question also came in from reader Joe Gelman last week:. 

“How do you see Community playing into the next phase of your career? Is it a new community services-focused company, leveraging community for your potential product, taking lessons from previously managing & growing communities? Something new? A combination of everything?”

Reminder: I’m answering a reader question in every newsletter, so send me your questions about community, life, business, how in the world the Giants are 2-0, or anything else you think I might be able to help with. Just hit reply.

My usual answer to this question is “I have no f'‘ing clue”. I have a lot of paths in front of me, but I don’t know which is the right one, and I’m hesitant to commit to any of them just yet, just like in the song.

There are a few things I do know:

1. What I don’t want (which I wrote about in my last newsletter)

2. I love writing, so I’m starting with this as a means to “get motion”, move a little further down the road, and change the view

3. I’d like to try making it as an independent creator

I’ve been an independent creator before, but quickly leaned into growing something big, and started hiring and growing CMX. For now, I’d like to stay solo, and just partner with people I respect on fun, finite projects.

In today’s newsletter, I thought I’d share some of the paths that are bubbling around in my head with you all. Maybe you’ll see something that seems obvious, and tell me “dude… just do that!”. Please do. Maybe it’ll inspire you to start something similar. Great! Steal my ideas. Maybe we’ll work on something together. If nothing else, it’s just helpful to get my thoughts down into words, and sharing them with you all is more fun than keeping them to myself.

So let’s do it…here are some of the paths I’m thinking about:

📰 This Newsletter

I’m starting with this newsletter and I already have questions I’ve been asking myself about its future.

A lot of newsletter creators I really respect, like Lenny Rachitsky, Casey Newton, Rosie Sherry, and Dru Riley, offer a paid version of their newsletter. I’m not sure I want to charge for this newsletter though. At CMX we tried launching a paid community alongside our free communities and I found it really difficult to know where to focus attention. If I had an idea for a post, should I share it in the free community or the paid? For this newsletter, I don’t want to have to decide if a piece should go behind a paywall or not.

I also don’t want to feel like I *have* to write here. I’m enjoying being able to write at my own pace. I like how my friend Nadia Asparouhova uses her newsletter, as more of a personal, creative outlet.

Charging for a pro membership also seems like one of the less efficient paths to generating income. I’ll share some of the high-level numbers I put together at the end of this newsletter. When compared to other channels, paid memberships are inefficient drivers of revenue unless you have a really large audience. They’re also a ton of work. Lenny, for example, offers a private community, a massive resource hub, pro-only articles… it’s a lot.

So for now, I plan on just keeping this newsletter free and building up an audience that can drive income in other channels.

🧠 Consulting

I’ve been doing consulting on and off for most of my career. It’s a great way to bring in money in the short run, but in the words of Naval Ravikant, “You are not going to get rich renting out your time.”

I do enjoy getting to work with a lot of different companies on their community challenges. Just this week I spoke with a company building communities around microschools, and a healthcare company building community around psychadelics. I love working on novel community use cases.

But if I do too much consulting it exhausts me. So I charge a premium and keep it capped at 3-5 clients.

If you’re curious, the way I structure my consulting is really simple:

I do two calls per month with the person or team, and offer unlimited asynchronous support over email where I can provide feedback on strategy documents, job descriptions, copy, articles, or anything else they need.

Sometimes my role looks more like a coach where I’m supporting an individual community professional with their work, career, internal politics, mental health, and anything else they need. Sometimes it’s working with a founder or team to launch a community and hire their first community lead. It’s whatever they need, as long as I have experience with it.

I’m doing consulting now, but it’ll just be a piece of the puzzle, not my main thing.

🤝 Talent Collective / Job Matchmaking / Recruiting

One thing I think I’m going to do is launch a job matchmaking service where I can connect companies who are hiring with great candidates and great candidates with high-quality jobs. 

I’ll vet the jobs and candidates. Companies would pay for access to candidates. 

I get a ton of inbound from companies hiring and candidates looking already. So I just need to put together a system to connect them at scale. I have a demo with a tool called Pallet next week that might make this real easy for me.

I think it’s something that will be really valuable for this audience and be a solid revenue driver.

I’ve experimented with traditional recruiting services before. I partnered with a friend of mine from childhood who worked at one of the largest tech recruiters in NYC. We were able to land a couple candidates in senior community roles, and recruiting definitely pays well (usually 10-15% of total annual comp). It was *really* time-consuming though, even with my friend doing a lot of the heavy lifting. It also felt like it clashed with how I naturally work. I love to make introductions, and I didn’t like having to hold back until a company signed a recruiting contract. 

I might try it again, but the first swing wasn’t a good fit for me.

🎤 Speaking and Workshops

I love speaking at events. I feel really comfortable and get amped up by being on stage. It’s a rush, and a powerful way to teach and connect with people.

I’ve never made speaking a big priority. I’ve just taken speaking gigs as they come. Since publishing my book they’ve come fairly frequently. Not enough to make a living but I could see it working if I focused on it.

 There’s a path I could see where I go all in on speaking, create a really slick keynote talk, and market it to conferences. I have friends who have been really successful and have made a lot of money doing this. If I could do it without overcommitting myself to traveling too much (don’t want to be away from my family too much), I think this path could be a lot of fun.

Like consulting, I don’t see this being my primary thing, but it could be a piece of the puzzle.

🧑‍🏫 A Course

I’ve always loved teaching. Over the last 8 years running CMX, I’ve taught dozens of workshops and have launched multiple online courses. The CMX Community MBA is still running and has trained many hundreds of community professionals in the business of community. I know this channel pretty well.

One thing I haven’t done before is a cohort-based-course (or “CBC” for short). I went through Maven’s first cohort on how to build a CBC and learned a ton about what it takes to make them successful. My fear is the time commitment for running a CBC regularly. But there are ways to offset the time commitment, like prerecording the content and only doing live sessions for Q&A once/week. Or bringing in teacher assistants to help with supporting students day-to-day.

Another consideration is how many courses there are out there now on community building. There are 10x more than when I first started building courses, and many of them are really good. I don’t want to overlap with what I already built at CMX, or with what others have already built. So I’m thinking about what unique angles exist that would bring something useful and exciting to the space. 

Two course ideas that have popped into my head recently: 

The Community Incubator: a course for forming a community hypothesis, testing it, and finding community-market fit, that you’d go through with a group of peers. Greg Isenberg’s Community College is sort of like this for building community products (starts Oct 3 if you’re interested). 

The Community Accelerator: a course for communities that have launched and have initial community-market fit, and are now looking to scale, implement better operations for growth, and take their community to the next level. They’d work together over something like 2-3 months, critiquing each other’s work, sharing what they’re learning, and supporting each other. 

Good ideas? Bad ideas? 

💸 A Fund

I’ve had a number of recent conversations with people who said that I should start a fund to invest in community software and community-centric businesses. I get a decent amount of deal flow from startups building in this space organically, and if I started building a fund, it’s likely we’d be able to see a lot of deals in the community space before anyone else.

I love startups. I’ve never worked at a big company before. Bevy was the biggest company I worked at with about 200 people (I joined through the acquisition when it was around 20). I’ve advised hundreds of startups over the years. Being able to support founders with more than just advice would be incredible. 

My fears here are many. I don’t know much about investing. The idea of being responsible for other peoples’ money scares me. And funds seem like really big operational lifts, which isn’t my strong suit. I would need a partner who loved the operational side of things to make this work. 

I’m also very aware that the world does not necessarily need another white, male, fund manager. There’s something that feels a bit cringe about adding to that plot line. On the other hand I’ve learned a great deal about doing DEI work over the years, and would bring those values with me, ensuring that money is reaching underestimated founders. Investors like Arlan Hamilton and Lolita Taub have set an incredible example that I’d love to follow.

I don’t think I’d pursue this path unless the perfect partner showed up, or I got to do it under the wing of an established fund.

🔧 Tinker on Products

Like any good entrepreneur, I’m infatuated with the idea of building and selling aggressively simple products that make passive income with minimal overhead. Some call these “micro-SaaS”. 

There are tons of little operational things that community pros have to do on a regular basis that can probably be productized. 

Some bad ideas with bad names I’ve come up with recently (feel free to steal):

• Vibes: A tool that automatically sent out surveys to your members and analyzes the data to give you an ongoing community health score based on qualitative feedback.

• The Daily Do: A subscription where every day you get one idea for a content/engagement idea to try in your community.

• Buddy System: A tool that matches up new members with a buddy who’s an experienced community member who opts in to support new members through their onboarding.

• Party Favors: A marketplace for experiences you can add to your events to make them more fun and memorable.

• WeReal: BeReal but for communities to share updates about what they’re doing right now, so you get a glimpse into other members lives.

Nothing has excited me enough to actually work on yet. 

🎧 The Podcast

I hosted the Masters of Community podcast for about a year and a half. It did well, nothing crazy but it grew steadily every month since we started it:

I enjoyed most of the conversations but it took a ton of time to put together. It was also really difficult to know what the impact was. I’d get occasional nice messages from people who said they loved it and some good reviews, but otherwise podcasts are sort of a black hole when it comes to getting feedback.

I don’t really know if it ever found podcast-market-fit.

I’m thinking about bringing it back just because I enjoy doing it, and it shouldn’t be too hard to get sponsors to fund it. But I’m trying very hard not to just fill up my workdays right now, and stay really focused on things that will bring in healthy income. 

If I’m being honest I also got a little bored of interviewing community pros at companies. It started feeling redundant. The conversations where I got the most energy were with authors, or people who started really weird and unique communities. I think it would be fun to do a show where I find interesting, obscure, and fast-growing communities and interview the founders about how they started. 

The podcast keeps coming up in my mind which means it’s probably something I’m going to pick up again. Some people think I should. I just don’t want to rush into it. If I do it, I’d want to go bigger this time around.

🔑 A Private Network for Community Executives

There are more community pros reaching Director, VP, and CCO levels now. There are very few places where they can have real conversations about the hard stuff they deal with. There’s always the risk of their employees or peers seeing it. It’s something I wish I had when I was VP at Bevy, but never had the time or energy to build it. To be honest I still don’t. 

I promised myself I wouldn’t start another community, damn it. 

–

That’s just some of the stuff I’ve been thinking about doing. Nothing is that groundbreaking, or really all that different from what I was doing before sabbatical while at CMX. 

I’m trying to find a better balance at this stage in my life where I work to live, and not live to work. If I can do what I enjoy and am good at, work a few days a week, bring in steady income, and have more time to spend with my family and myself, that’s winning. Steve Schlafman’s newsletter recently shared a quote from our mutual friend Jonathan Basker who said, “For a long time I thought I wasn’t ambitious until I realized my ambition is to live a good life.” I like that. 

I can’t turn off my ambition… I’m wired to try to accomplish. But if I look at life as the thing I’m trying to accomplish, maybe I can channel that energy in a healthy way.

Something else might come along and catch my imagination, convince me to go back to starting or building a company. It’s happened several times in the past. But it would have to really knock my socks off. And I haven’t been wearing socks lately, so that’s going to be tough. 

I promised to share some of the numbers for each path. Whatever I do, I want to know how likely it is that I can be financially independent doing it. So I mapped out what reasonable monthly and annual income might look like for some of these paths, as well as how many hours per month I’d likely have to spend on it, and here’s what I came up with:

Note: Something I’d like to do in this newsletter is be really transparent about money and numbers as I’m navigating this space. If you have any questions, just let me know.

These numbers are primarily for the first year. I have to map out what they would look like in years 2, 3, etc. Some channels are more efficient in the short run, but hard to scale over the long run, like consulting. Whereas things like newsletter subscription businesses or on-demand courses can scale up since it doesn’t take more time to support more customers. 

I’d love to hear from all of you. I’m putting this out there in part to get it out of my head and in front of all of you so you can tell me what resonates. Maybe there’s something obvious you can all see that I can’t. Tell me!

I’d also especially love to hear from you if you’ve figured out how to be a financially independent creator. What lessons do you have to bestow upon me?

Hit reply or drop a comment and let me know what resonated from this post, or what your experience has been.

See you soon!

-David