This is the Golden Age of the Subscription.

They are on my mind. A lot.

Everywhere we turn, a service is asking for our credit card so it can charge us $20 a month for the rest of our lives for some amazing thing only it provides.

While I wrote before about deciding to not pay for a service I love, sometimes a subscription is worth every penny spent. That’s how I think about the $20 I spend each month on Claude Pro.

But is that a wise use of my money?

You bet your bippie it is.

Remaining Relevant

Here’s a sneak peek at the things Claude and I have done together over the last four weeks.

I used Claude to finish building my own private dictation app to use on my MacBook. And I am planning a vacation, complete with companion website, for a milestone birthday celebration.

I could go on, but that laundry list wouldn’t capture the crux of why I pay Anthropic, the foundation lab responsible for Claude. It’s not about what I have done with it. Instead, the key for me is what the subscription makes possible.

Mark Schaefer said it well in a recent episode of “Grit & Gravitas,” the Anne Deeter Gallaher and Anne Carnathan podcast:

“AI, it’s like putting on a new set of armor…. It can make you more of yourself at your best.”

Because AI is changing our world, and because the pace of the change we’re experiencing today will inevitably accelerate, and because the only way to learn about that change is to experience it firsthand, Claude is my investment today to continue being relevant in the future.

Table Stakes

If you are using AI today, congratulations. It’s a critical first step.

But if you aren’t paying for AI, I urge you to select one of the frontier models – ChatGPT, Claude, or Gemini – and start a subscription today.

Why?

To really understand this technology, and to be prepared for what is ahead, you need to be a regular AI user. And not just for recipes or making images or simple search, although those things can be fun.

You need to push yourself by pushing your model of choice as far as it will go. Press it to do things you’re not quite sure it can handle.

I didn’t know if Claude could combine 77 documents into a single document in chronological order with dates in different formats across the set of files. It did that this weekend, and I believe it could have done much more.

For you, the subscription will open a couple of locked doors.

First, you’ll have higher usage limits and early access to the best new models. By paying for Claude, I get access to each new model as soon as it is released and, by being wise about the model I select, can do significant work far longer than I could on the free plan.

Also, and likely most important, since you are paying for the service, you will be more compelled to spend time with it and to identify more ways it can help you. By spending 20 to 30 minutes with your AI, you will become more proficient faster.

Or, building on Mark’s analogy, your armor will be stronger and shinier.

A Guide to Decide

If you already use one specific AI tool, there’s no reason to not invest there. It already knows something about you, and you’ve likely already tweaked its privacy settings.

If you don’t have one go-to model, here is a prompt, generated by Claude, you can copy into an AI chat to help guide your decision:

I want your help choosing which AI subscription is right for me. Don’t just
list features — interview me first, one question at a time, so your final
recommendation actually fits my situation. Wait for my answer before asking
the next question. I may or may not be working right now — don’t assume
either way.

Ask me about:

1. Who I am and what fills most of my time these days — this might be a
   job, a business I run, a transition I’m in, retirement, caregiving,
   volunteering, or some mix of these. Don’t assume I’m employed.
2. Where I am in this life or career stage right now, and where I see
   myself in the next 1-2 years. (Climbing in a field, pivoting, building
   something of my own, winding down toward retirement, settling into
   retirement, or staying active and engaged on my own terms.)
3. What I already use AI for today, if anything — even informally.
4. What I expect to need or want AI for in the next 12-18 months. Push me
   to be specific, and don’t limit the menu to work tasks. Depending on my
   answer to #1, this could include any of: writing or research, coding,
   data analysis, image or video creation, customer-facing work, managing
   a team’s AI use, planning travel, managing health information and
   appointments, staying connected with family, pursuing a hobby or
   creative project, or learning something new for its own sake.
5. How I like to work with new tools — do I want something that works well
   out of the box, or am I willing to spend time customizing and learning
   a more powerful but complex tool?
6. Anything that matters to my decision: budget, whether an employer is
   already paying for something, data privacy concerns, tools a team or
   company already standardizes on, or how comfortable I am generally with
   new technology.

Once you have my answers, give me:

• A clear primary recommendation with your reasoning
• One honest alternative, and the specific situation where I should pick
  that one instead
• 2-3 concrete first tasks I should try in week one, based on what I told
  you I actually need
• A note on what might change in 12-18 months that could affect this
  choice, so I know what to revisit later

Be direct. If my stated needs don’t match what I think I want, tell me so
before you give the recommendation.

Already paying and not sure if you are getting the full value of your subscription dollar? Let’s talk.

Book a free 15-minute call with me to discuss where you are with AI, where you want to get to, and how I can help.

No credit card required. Honest.