Why Personal Planning Tools Cost What They Do (And What I Learned Building One)
Published
Jul 29, 2025
Topic
Thoughts
So last month I'm sitting with my friend, and she's basically having a breakdown about her goals again.
Smart woman, knows exactly what she wants - learn Spanish, get back in shape, maybe start that side business she's been talking about for two years. But every single plan falls apart around week 3. Every time.
She pulls out her phone and shows me this graveyard of apps. Habitica ($7/month), some AI coach thing ($29/month), even tried actual human coaching at $25 a week for like three months. Nothing stuck.
And I'm listening to her, right? And something just... clicked for me.
All these tools treat goal-setting like everyone's brain works the same way. Like there's some magic formula that works for all humans. Which is obviously bullshit if you think about it for like five seconds.
The thing nobody talks about
Here's what I realized building my own planning tool: most personal development apps aren't really trying to help you succeed. I mean, they think they are, but their business model is completely backwards.
Think about it. A habit app that charges $7/month needs you to stay subscribed. Whether you actually achieve your goals or not doesn't really matter to their bottom line. Actually, if you achieve everything in month one and cancel... that's bad for them financially.
They need thousands of people paying monthly just to keep the lights on. Servers, customer support, developers, marketing to get new users when people inevitably quit.
It's this weird incentive mismatch where success for you might mean failure for them.
My ADHD brain ruins everything (as usual)
Okay so here's where this gets personal for me. I have ADHD, which means my brain basically laughs at traditional planning advice.
"Just break it into smaller steps!" Cool, my executive function is broken, so that doesn't help.
"Use a calendar!" Great, I'll forget to check the calendar.
"Build consistent habits!" Sure, let me just ignore the fact that my energy and focus change wildly from day to day.
Most planning tools are built by neurotypical people who assume everyone's brain works like theirs. Which is... not how neurodiversity works, obviously.
But here's the thing - when I actually find tools that work with my ADHD instead of against it, I can accomplish insane amounts of stuff. Like, scary productive. The problem was never my ability to achieve goals. The problem was that nobody was building tools for how my brain actually operates.
So I built something different (probably overcomplicated it)
After watching Sarah struggle, and remembering my own graveyard of failed planning attempts, I started building my own system.
Not a platform. Not a subscription service. Just... a thing that generates really good plans and then gets out of your way.
The process is kind of wild:
Claude analyzes your situation - like really analyzes it, considering your constraints, your brain type, your energy patterns
Perplexity researches current info relevant to your specific goal (not generic advice)
The system synthesizes all of this into a personalized 90-day plan
DeepSeek formats it so it actually makes sense for how you process information
Then it sends you this comprehensive guide and basically goes to sleep until you need another one.
I think the key insight was: you don't need constant engagement. You need really smart planning that fits your actual life.
Why people actually fail at goals (spoiler: it's not willpower)
Building this taught me that goal failure usually isn't about motivation or discipline. Most people fail because the plan itself is fundamentally incompatible with their reality.
Like, your plan assumes you have two hours of free time every day, but you've got kids and a demanding job. Or it requires consistent energy levels, but you're dealing with depression or chronic illness. Or it's structured for someone who loves routines, but you get bored and need variety to stay engaged.
The plan fights against how you actually live instead of working with it.
I've watched people call themselves "lazy" or "undisciplined" when really they just had a plan designed for someone else's life.
The technical rabbit hole I went down
Okay this is probably only interesting if you're into the technical side, but building something that actually adapts to individual thinking patterns was... complex.
Most personal development tools are basically databases of generic advice. "Here's what works for most people, maybe it'll work for you too."
But I needed something that could:
Actually understand individual cognitive styles
Pull current, relevant information (not just rehash old advice)
Combine personal factors with general principles intelligently
Present information in whatever format works best for that specific person
Which is why I ended up using multiple AI models instead of trying to make one do everything. Claude is incredible at understanding nuanced human situations. Perplexity finds current, specific info. DeepSeek structures complex plans without making your brain hurt.
Each one does what it's best at, then hands off. Probably overkill, but it works.
What I learned about pricing (accidentally)
When I finished building this thing, I had no idea how to price it.
Looking at the market:
Basic habit tracking: $7/month
AI coaching: $29/month
Human coaching: $25/week (that's $1,300 a year!)
Course platforms: $360/year
But here's the thing - my system generates way more sophisticated plans than any of these. Like, the kind of analysis you'd expect from a really good human coach, but it factors in way more variables than a human could track.
So should I charge coach prices? Seems excessive.
Then I realized: most people don't actually need a new life plan every month. Maybe every quarter when things change. Maybe twice a year when you hit a major transition.
Why would you pay monthly for something you use occasionally?
So I priced it at $49 per plan. One time. You get this incredibly detailed, personalized strategy, then you go execute it without worrying about subscription fees.
Makes more sense to me, anyway.
Testing it in the wild
I've had maybe 40-50 people use this now, and some patterns emerged that surprised me.
The people with ADHD had this almost relief response. Like finally, something that gets how their brain works instead of fighting it.
But even neurotypical people responded well to having their actual constraints acknowledged. One guy said it was the first time a planning tool asked about his commute time and factored that into his schedule.
Sarah (remember Sarah?) used it for her Spanish learning goal. The system figured out she's an auditory learner with limited morning bandwidth, so it built a plan around podcast-style lessons during her commute. She's actually sticking with it this time.
Another person wanted to transition careers. Instead of generic "network more" advice, it analyzed her current skills, researched her target industry, and created this step-by-step approach that fit around her current job demands.
The difference seems to be that it starts from where you actually are, not where some idealized version of you should be.
What I actually think about goal achievement now
Building this changed how I think about personal development tools entirely.
Most expensive doesn't mean most effective. Most popular doesn't mean most useful for you specifically.
The best tool is the one that helps you achieve what you're actually trying to achieve, considering how your brain actually works and what your life actually looks like.
I think people already know what they want to accomplish most of the time. They just need a plan that fits their reality instead of some fantasy version of perfect conditions.
Maybe we're doing software wrong
This whole experience made me think we might be approaching personal development software backwards.
The subscription model works great for things like email or cloud storage - services you use constantly. But for planning? You might get better results from something that delivers really high-quality output occasionally rather than mediocre engagement daily.
Like, what if instead of trying to capture your attention every day, software just solved your problem really well and then got out of your way?
I think the technology exists now to build tools that genuinely understand individual needs. The question is whether we'll use it to actually help people or just optimize for more engagement and subscription revenue.
For personal development stuff, seems like an obvious choice to me.
But maybe I'm biased because I'm tired of subscription fatigue and tools that treat my ADHD brain like it's broken instead of just different.
Either way, building this taught me that there's definitely room for software that works with people instead of trying to change them into ideal users.
Which feels like it should be obvious, but apparently it's not.