Why I Started Documenting My Own Adulting To Do List (And What I Hope It Does For Yours)

I want to start by telling you something that still feels a little embarrassing to say out loud…

I am a former contracts and trademark lawyer. I spent years in a law practice where part of my job was estate planning. I understand how to read fine print. I have genuinely read entire member guidelines, from top to bottom—for fun.

And my son was almost six years old before I had a will.

Not because I didn’t know it mattered. Not because I hadn’t thought about it. I knew every reason why we needed one. But every time I went to actually sit down and do it, I’d realize I first needed to figure out all the accounts my husband had, or get more life insurance in place, or figure out where in the budget we could add that premium. One thing led to five other things, and the overwhelm would win every time.

I’m telling you this because I think a lot of you have your own version of that story. And I want this to be a place where we don’t have to pretend otherwise.

How The Adulting Diaries Actually Started

Before Decide with Chelsea existed, I was running a YouTube channel to build awareness for a paid membership community. Every once in a while I’d throw in a video about something I personally used and loved — a little playlist I called “Chelsea Loves.” Nothing fancy. Just me talking about things my family actually uses.

One of those videos was a review of CrowdHealth, which is the alternative to traditional health insurance my family switched to after I had a medical billing nightmare that I still haven’t fully resolved. I got an MRI that I believed would be covered by the private insurance I was paying for. The doctor coded it incorrectly. It fell into a coverage gap. I couldn’t figure out how to fight it. I ended up on a payment plan that I am honestly still paying off. And I decided I was done handing $1,400 a month to an insurance company that was impossible to actually use.

So I researched alternatives.

Research To Find the Services and Resources That Are More Supportive For Me and My Family

I went deep — like, 13 tutorials and the entire Member Guide deep — until I understood exactly what CrowdHealth was, how it worked, who it was right for, and who it wasn’t. Then I made a video about it.

That video got dozens of comments and questions in the first week. And so many people started using my referral code to get a discount and try it out for themselves. I sent the video and my discount code to a few friends who had been asking what we do for insurance, and they came back saying it was the most helpful review they’d seen — that it actually helped them understand whether it was a good fit for them specifically.

“Thank you for taking the time to answer my question on a video. You were so thorough and it really helped me decide that this is a good fit for me.”

I sat with that for a while. Because what I kept noticing was that so many accounts exist to put a product on your radar—to go viral, to raise awareness about a brand. But then when you get to the actual question of “but will this solve my specific problem?”...you’re on your own.

Nobody answers that question. And that’s exactly where people get stuck in their own research. Not quite sure if it’s a good fit for them, so then they just leave that mental tab open and don’t check it off their list to completion.

Research For Your Adulting To Do List—Done For You

I started thinking about how many times in any given week someone in my life texts me asking what supplement I’m taking, which air filters we bought, how I’m structuring our budget. I am the person in my friend group that people reach out to.

I think it’s a combination of being autistic and being a lawyer, but I am probably the only person I personally know who actually reads the full member guide before signing up for something, or watches all the tutorial videos for a budgeting app before deciding to use it.

So my friends just trust me to have already done the research.

But I also realized: I didn’t want to create content about random things and just be an infomercial. I wanted to create content about things I personally needed accountability on. And for me, that’s the adulting stuff. The things that feel overwhelming, that I can easily put off indefinitely, and that no one in my life is going to celebrate when I finally do them.

The Part I (and most adults) Don't Usually Talk About: The Shame Piece

I am AuDHD (meaning I am an autistic adult who also has ADHD) and my neurodivergence has created a lot of shame for me around the adulting stuff specifically. There’s this feeling that everyone else has figured out how to be a responsible adult without it completely overwhelming them. I can hyperfixate and solve wildly complex problems for clients. I can build systems from scratch and make them simple to explain and pass off. But remembering to register my car on time? Having a monthly money meeting with my own budget? That feels like a Herculean effort sometimes.

The tasks that keep us financially secure and legally protected…they are not high-dopamine tasks. And many of them just go on “until the end of time” which can feel so de-motivating. Nobody celebrates when you make a payment on time, or finally get your estate plan done, or set up a high-yield savings account. There’s no confetti. There’s no notification. And for a brain that runs on novelty and reward, it is incredibly easy to put those things off endlessly while doing literally anything else.

And I think the shame compounds it. Because the longer you put something off, the worse you feel about not having done it, and the harder it becomes to start. It becomes this thing you just… live with, silently. Hoping no one asks.

HERE'S WHAT I WANT YOU TO KNOW:

Most people are more likely to talk about their sex lives than about how they’re investing their 401(k). Nobody taught us this stuff. Our education system doesn’t teach life skills or financial literacy.

We are all largely starting from scratch unless our families specifically gave us that foundation. The shame you feel about not having it figured out? That’s not a character flaw. That’s an entirely predictable outcome of a system that never equipped us for this.

What I Actually Do, And Why It Matters To You

I am multi-passionate and a maximalist when it comes to trying to help people. I run 3 businesses. I consult on systems and operations for expert and service-based businesses. I’m launching a trademark law practice in 2026. I run Decide with Chelsea. I homeschool my son part-time. I manage all the communications for his outdoor school, his sports teams, our family’s supplement subscriptions, all of our doctors and appointments. My husband has a demanding job with long days, and we both have variable income, which means the financial management falls entirely to me—and it’s more complicated than it would be with a predictable paycheck.

Some days it just feels like too much to stay on top of. When we sign my son up for something new and they tell me I need yet another app to manage the schedule, I genuinely want to cry.

I tell you all of that not to complain about how busy I am, but because this is the context in which I am doing this work.

I am not a financial guru living a streamlined, optimized life who has arrived at the promised land and is handing down wisdom from above. I am not selling you a course, a planner, or a tracker.

I am a person who is actively, imperfectly, month by month trying to get my family’s adulting ducks in a row. And I’ve been doing it since 2024; tackling one or two bigger projects a month. Some months it carries over to the next. That’s okay. The progress is adding up.

The Origin Stories Behind the (products / services / programs) I Recommend

Here’s what I want you to understand about every product or service I talk about on this platform: there is an actual story behind why I use it. These aren’t things I agreed to promote and then researched. These are things that solved a real problem for my family, often after something went wrong first. And once I loved it, I figured out if there was an affiliate program, or a way to get a discount for people I recommend it to.

The MRI I just told you about? That’s why we use CrowdHealth.

The mold situation — where we unknowingly lived in a home with mold levels 1,000 times higher than is safe, lost about 80% of our belongings including most of our important paper documents during remediation, and spent years replacing social security cards and passports and trying to rebuild a system that would actually work-that’s why I want to complete a NokBox organizer. Losing irreplaceable documents in a crisis, and knowing that if we’d had a grab-and-go system it wouldn’t have happened, changes how you think about being prepared.

The estate plan I kept putting off despite having done estate planning as a lawyer? That’s why we used Trust & Will. I needed something where I could do it myself to save money, but trust that it was done correctly. And we actually did it. My son is six. It’s done. I can stop carrying that one.

Monarch Money came from working with a money coach who finally set up a budget dashboard that made sense to my brain (after two prior coaches who wanted me to use spreadsheets that hurt my head). I started using the budget to run little side quests for myself: what levers can I pull to decrease our monthly expenses? Can I get a better mortgage rate? Can I lower our insurance costs?

It turned adulting into something I could actually engage with instead of avoid.

What To Expect From My Adulting Diaries

The Adulting Diaries is where I document what I’m working on. The things I’m researching, the decisions I’m making, the ones I’ve been avoiding, the ones I finally crossed off the list. It’s accountability. It’s the body doubling that actually helps my brain engage with tasks that aren’t exciting but matter enormously.

But it’s also for you. Because I know that a lot of people have a running list of things they know they should do: set up life insurance, look into estate planning, get a better handle on their budget, understand their health coverage optionsand that list just keeps growing while life keeps demanding their attention.

I don’t want to just put another sticky note on your metaphorical fridge. I want to send you the link, explain why something may or may not be a good fit for your specific situation, and give you a discount code in case you decide to move forward. I want to answer the lingering specific question that’s been holding you back. And I want to create a place where checking something off that list (even the unsexy, unglamorous stuff) is worth celebrating.

ADULTING WINS WE CELEBRATE HERE:

• Finally logging into your 401(k) for the first time

• Getting your NokBox folders set up

• Making a decision about health coverage for your family

• Getting your estate plan done

• Opening a high-yield savings account

• Having the money conversation you’ve been avoiding

Welcome To The Adulting Diaries. Let's Go Check Some Things Off Your List Too...

You are not behind. You are not dumb. These systems were not designed to be navigated by regular people without expensive professional help. The fact that you’re researching, that you have tabs open, that you’re trying — that counts. A lot. You just need someone to help you cross the finish line.

That’s what I’m here for.

Not as an expert, not as a guru, not as an influencer trying to sling affiliate links. As the friend who already has 30 browser tabs open, has read the member guidelines, and will give you an honest breakdown — including who something isn’t right for — so you can make your own informed decision and get on with your life.

Some blog posts contain affiliate links or discount codes - when you use those links or codes, I will make a little money for referring you, paid directly from the company. It never costs you more to use my link, and I only recommend products, services and software I research, use and trust myself.

Your support is appreciated, as it helps to fund me creating more free educational content like this.