How to think about 2026 if you're not where you wanted to be

A reflection on measuring the wrong things, choosing comfort over growth, and what to do differently in 2026

Hello, friends! Whether this lands in your inbox or you’re catching up on the site, thanks for reading. This one’s a bit of a year-end audit... what worked, what didn’t, and how to avoid repeating the same mistakes in 2026. (There are some planning questions at the end if you’d like to work through this yourself.) If you’ve been building something this year and it’s been slower or messier than expected, this one’s for you. I hope it helps spark a few questions worth asking, and if it does, I hope you’ll share it with someone else who might need the same reminder. x

As the year begins its initial phase of wrapping up, I’ve been sitting with this uncomfortable realization for the past few weeks. The kind that sneaks up on you when you’re looking back at the year and trying to figure out what actually happened. On paper, 2025 was good. I spent most of my time and energy building and experimenting on Substack. I technically joined the platform in 2024, but I didn’t start posting regularly until April of this year—when I decided to take this (and myself) seriously, and set a goal to become a full-time writer by 2026.

Between April and today, I’ve grown my Substack from 500 to 13,000 readers, with 250 being paid.¹ A surreal achievement, something I do not take for granted, and am very proud of. (Thank you for being here, seriously!) In that time, I spent countless hours researching and writing, I published over 100 essays and articles—two of which “went viral,”² and I rebranded from WILD BARE THOUGHTS to BAD GIRL MEDIA because I felt it was more aligned with my overall mission.³

By most visible metrics, it looks like I’m on track.

But when I look at the actual sustainability of what I’m building, something doesn’t add up. The subscriber growth is real and meaningful, but I optimized for the wrong number. I was watching subscribers go up and feeling good about it, but subscribers alone don’t determine whether this works as a living. Revenue does. And my revenue isn’t anywhere close to where it needs to be for this to actually sustain my life. At my current pace, I won’t hit financial sustainability until mid-2026, maybe later if I’m being realistic. I also wanted to bring on more writers and independent journalists for BAD GIRL MEDIA before the end of the year—to start building something bigger than just my own output—but I’m far from that goal, as well. Lastly, I committed to saying yes more this year, to networking and opportunities and visibility that makes me uncomfortable, but I can count on one hand the number of times I actually followed through.

So I’m growing, and I’m on a track, but I’m starting to realize it might not be the right track because I never actually defined where it was supposed to go. The problem isn’t that I didn’t make progress, the problem is that I set goals without defining what they actually meant in concrete terms, and now I’m at the end of the year trying to figure out what I was even aiming for in the first place.

This isn’t about complaining that things didn’t work out, it’s about recognizing a pattern I see everywhere, including in my own work this year. We set goals that sound good without defining what they actually mean, and then we’re surprised when we end up somewhere we didn’t intend to go. If you want to build something sustainable—whether that’s a writing practice, a business, a creative career, whatever—you need more than good intentions and visible progress. You need clarity on what you’re actually building toward and a realistic plan for how to get there.

That’s what I’m trying to figure out for 2026, and if you’re in a similar position of realizing you’re not quite where you hoped to be, maybe this will be useful for you too.

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The trough of sorrows.

If you’ve been building anything for more than a few months, you know about what Paul Graham⁴ calls the “Trough of Sorrows.”⁵ It’s that long, grinding middle period where the initial excitement has completely worn off and the results aren’t coming fast enough, and you start to wonder if what you’re doing is actually working or if you’re just fooling yourself. I find myself in the trough every few weeks, sometimes more often than that. When I’m in it, everything feels pointless. The work that felt energizing and meaningful last month suddenly feels like pushing a boulder uphill with no end in sight. I start questioning whether I’m cut out for this at all, whether I should just get a “normal” job, whether I’m wasting my time on something that will never pan out.

This is usually where people tell you to rest. To take a break, “listen to your body,”⁶ honor your need for downtime. And sure, rest is important. Burnout is real and I’m not trying to diminish that. But the part nobody wants to say out loud because it sounds too much like hustle culture bullshit is: resting when you should be working isn’t going to help you reach your goals. If there’s work that needs to be done, work that will genuinely take ten hours of focused effort, you can’t just rest and expect it to magically do itself. At some point, no matter how you feel about it, you have to sit down and put in those ten hours.

I think the distinction matters here because there’s this conflation happening where people act like any acknowledgment that hard work is necessary is somehow toxic. Not everyone wants to hustle or grind their life away, and that’s completely fine. But exceptional things don’t happen unless you’re putting in an exceptional amount of effort. You don’t stumble into the life you want. You build it, deliberately and often uncomfortably, even when it feels hard and even when you’d rather be doing literally anything else.

What I’ve learned is that having really clear, actionable goals becomes especially important when you’re in the trough. When nothing feels inspiring, when you’re in a creative rut or stuck in some emotional funk, you need something concrete to grab onto. You need a task that doesn’t require motivation or inspiration to complete, just execution. This is why vague goals are so dangerous. “Become a full-time writer” sounds inspiring when you’re feeling good, but it’s completely useless when you’re in the trough because you have no idea what to actually do next. On the other hand, “publish two paid subscriber posts this week and send three pitch emails to larger publications” is boring as hell, but it’s actionable. It doesn’t care how you feel. It just needs to get done, and you know exactly what done looks like, and what steps you need to take to get there.

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What went wrong in 2025.

Looking back at 2025, I can see the mistakes more clearly now that I’m willing to be honest about them. The first and biggest one is that I set a goal without defining what it actually meant. “Full-time Substack writer by 2026” sounds great on paper. It sounds like a real goal. But what does that actually mean in practice? How much revenue do I need to sustain my life? How many paid subscribers does that translate to at my current pricing? What’s my conversion rate from free to paid, and is that rate even realistic to maintain? I didn’t answer any of those questions. I just set the goal and hoped it would work itself out somehow.

The second mistake, which connects directly to the first, is that I measured the wrong thing entirely. I was tracking subscriber growth because it’s visible and measurable and feels good to watch go up. There’s real value in having an audience who shows up to read what you’re writing, and I don’t want to diminish that. But I made the error of treating subscriber count as a proxy for sustainability when the actual metric that determines whether this works as a career is revenue. I could have ten thousand or fifty thousand subscribers, but if the conversion rate to paid is too low or the pricing doesn’t support the life I’m trying to build, then the subscriber number is just a vanity metric. It looks impressive but it doesn’t actually tell me if this is working.

I also chose comfort over discomfort in key moments throughout the year. There were opportunities where I could have pushed harder, reached out to bigger publications, pitched more aggressively, said yes to things that scared me, and I didn’t. I told myself I was being intentional with my time, that I was focusing on what mattered, but the truth is I was just avoiding discomfort. I was choosing the easier path because the harder one felt uncertain and uncomfortable, and now I’m paying for those choices with slower progress than I wanted.

And maybe the biggest tactical mistake was that I didn’t set any checkpoints along the way. I made this vague annual goal back in April and then just didn’t check in on whether I was actually on track until now, in November, when it’s almost too late to course-correct for the year. No quarterly reviews to see if I was hitting the benchmarks I should be hitting. No monthly audits to catch problems early when they’re still small and fixable. Just vibes and hoping for the best, which turns out is not a great strategy for building something that needs to be sustainable.

“Would you tell me, please, which way I ought to go from here?” asked Alice.

“That depends a good deal on where you want to go,” said the Cat.

From Alice’s Adventures in Wonderland by Lewis Carroll (1865)

How to think about 2026 differently.

So here’s what I’m trying to do differently as I think about 2026, and what I’d suggest if you’re in a similar position of realizing you’re not quite where you hoped to be. The first thing is to define success in actual concrete terms instead of vague aspirational language. Not “grow my business” or “become a full-time creator” but actual numbers that you can measure and track. How much money do you need to make? By when? Break it down monthly so you know what you’re actually aiming for. If you need sixty thousand dollars a year to go full-time on something, that’s five thousand dollars a month. How many paid subscribers at what price point gets you there? What’s your current conversion rate from free to paid? Do the actual math and make it real instead of just hoping it works out.

For me, this means getting brutally clear on my target monthly revenue and working backward from there to figure out what has to happen to make that number real. No more vague “I want to grow” energy. Instead, I need this specific number of paid subscribers at this specific price point by this specific date, and if I’m not on track for that, I need to know why and fix it.

The second thing is to identify the specific actions that actually move the needle instead of just saying you’ll “work harder” like that means anything. What are the three to five things that, if you did them consistently, would directly get you closer to your goal? Not busywork that makes you feel productive. Not things that are easy and comfortable but don’t actually matter. The things that genuinely impact revenue or reach or whatever metric you’ve decided actually matters for your goal.

For me, it’s probably something like publishing consistently without letting weeks slip by, improving my conversion rate by getting better at CTAs and paywall positioning, pitching to larger publications for visibility even though it makes me uncomfortable, and actually networking instead of avoiding it because people exhaust me. Those are the things that will move the number. Everything else is just noise.

The third thing, and this is the one I failed at completely this year, is to set actual checkpoints and then use them. Monthly is probably the minimum frequency that makes sense, but quarterly might be more realistic depending on what you’re building and how fast things move. But you have to stop at those checkpoints, look at the actual numbers, and ask yourself if you’re on track. If you’re not, you have to ask why not and what needs to change. And here’s the uncomfortable part that I’m trying to get better at: you have to be willing to actually change course if the answer is uncomfortable. The checkpoints are completely useless if you don’t actually act on what they tell you.

The fourth thing is to get honest with yourself about where you chose comfort over discomfort this year. This is the one that stings the most when you actually do it. Look back at 2025 and identify the specific moments where you could have pushed harder and didn’t. Where you chose the easier path because the harder one felt uncertain or uncomfortable or like it might not work. Where you avoided something because it required you to be vulnerable or visible or risk failure.

Those moments are your leverage points for 2026. That’s where the growth is hiding. That’s where the distance between where you are now and where you want to be gets closed. If you keep choosing comfort, you keep getting the same results. If you want different results, you have to be willing to be uncomfortable more often.

And the last thing, which ties back to the trough of sorrows, is to build systems that work even when you’re in a funk. When you’re in a creative rut, when motivation has completely disappeared, when everything feels pointless and you’re questioning all your choices, you need a system that doesn’t care how you feel. A checklist or a routine or a set of non-negotiable tasks that get done whether you’re inspired or not. Because here’s the truth that nobody wants to hear: you’re going to end up in the trough again next year. Probably multiple times. And when you do, you need something to grab onto that isn’t dependent on feeling good or motivated or inspired.

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The work still has to get done.

I keep thinking about this tension between the cultural emphasis on rest and the reality that exceptional results require exceptional effort. Both things can be true at the same time, which makes it complicated to talk about without sounding like you’re either glorifying hustle culture or dismissing the very real problem of burnout. Rest is genuinely important. Burnout is genuinely real. I’m not trying to diminish either of those things. But also,

if you want something that most people don’t have, you have to be willing to do things most people won’t do. That’s just how it works.

The work doesn’t do itself. The ten hours don’t magically happen because you took a nap and listened to your body. At some point, whether you feel like it or not, you have to sit down and do the thing. The goal isn’t to hustle yourself into the ground or to work every waking hour until you collapse. The goal is to get so clear on what you’re building and why it matters to you that you’re willing to do the work even when it’s not fun. Even when it’s boring. Even when you’d rather be doing literally anything else. That clarity is what separates people who hope things work out from people who make sure they do.

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Questions to ask yourself about 2026

If you’re sitting here at the end(ish) of 2025 realizing you’re not quite where you wanted to be, here are some questions that might help you get clearer on what actually needs to change. Take your time with them. Write out the answers somewhere you can actually see them instead of just thinking about them in your head. Get specific about the numbers and the actions and the uncomfortable truths, because vague answers won’t help you any more than vague goals did.

• What goal did you set this year without defining what it actually meant in concrete terms? What does that goal look like when you translate it into measurable numbers and specific outcomes?

• What metric were you optimizing for that didn’t actually move the needle toward what you want? What should you be measuring instead?

• Where did you choose comfort over discomfort this year? What opportunities did you avoid because they felt hard or uncertain or like they might expose you to failure?

• If you’re being completely honest with yourself, what’s the actual amount of focused work in hours that your goal requires? Have you been putting in that time consistently, or have you been avoiding it while telling yourself you’re being strategic?

• What are the three to five specific actions that, if you did them consistently throughout 2026, would directly move you toward your goal instead of just making you feel busy?

• What checkpoints will you actually set for yourself to track whether you’re on course? Monthly reviews? Quarterly audits? And more importantly, what will you actually do if you’re off track at those checkpoints instead of just noticing and continuing anyway?

• What system can you build that works even when you’re in a creative rut or emotional funk, something that doesn’t require motivation or inspiration, just execution?

Take some time with these questions. Sit with them. Get specific about what you actually want and what you’re actually willing to do to get it. Because 2026 is coming whether you’re ready or not, and vague goals won’t get you any closer to where you want to be than they did this year. (I’m talking to myself here, more than anyone else.)

The good news, if there is any, is that you still have time to get clear. You still have time to define what you actually want and build a real plan to get there instead of just hoping it works out. You just have to be willing to do the uncomfortable work of being honest with yourself about where you are and what needs to change. And then you have to be willing to actually do the work, even when it’s not fun, even when you’re in the trough, or even when you’d rather be resting.

That’s what I’m trying to figure out how to do better in 2026. Maybe you are too. And if you are, I hope this helps you get unstuck, get clear on what you’re aiming for, or even just to simply start thinking about thinking about what to do next. You have the power to create the life you want. I hope we all find ways to harness that power—and by the way… we don’t have to wait until 2026. We can start today! :)

PS: If you enjoyed this post, I recommend “Building a mind that can’t be fucked with” or “THE GUIDE TO: self-sovereignty” next.

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1. I shared my 9 hard-earned lessons from building on Substack here.

2. Taste is the new intelligence was originally published in April 2025, but started to pop off at the end of May/beginning of June & The quiet thrill of not being for everyone was published in mid-July and pretty much went unseen until it picked up steam mid-October. There’s a lesson in here, too—don’t assume things flopped. The shelf life for posts on Substack is lonnnng, and you never know when people will stumble on your work. Just, keep, going.

3. I wrote a little note about the rebrand here.

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5. Graham’s original graph shows it as “Trough of Sorrow” (singular), but I’ve seen it written both ways (and I personally prefer the pluralized version). Either way, you’re miserable.

6. My body mostly tells me to eat snacks and avoid uncomfortable conversations, so this advice has limited utility.