I spent the last two weeks of August redesigning my website. It’s been a humbling, eye-opening experience that has taught me a lot about getting things done with limited resources.
I’ve created and maintained websites for other organizations in the past, but on-staff tech support was always a phone call away in case I ran into trouble. (Tip: don’t install any updates at 4:50 PM on a Friday afternoon.)
Now that I have my own business, the process has changed quite a bit.
You’re probably wondering,Why not outsource the work to a professional?
Two reasons:
First, I enjoy working on websites. It’s fun to puzzle through the technology, and I find it immensely satisfying to create something concrete and functional.
Second, I need a dynamic website that I can update easily. I want to understand how things work so that I can make changes on my own timeline.
At the same time, the rise of AI has shifted the calculus from a simple DIY-vs.-outsource choice to a three-way decision: DIY, outsource, or leverage AI. For example, my WordPress theme of choice (Divi) now bundles AI into its offerings and claims to be able to design complete websites in minutes.
In my consulting work, I find that many groups that were hesitant to spend money on an external consultant now embrace AI for nearly every task. Yet as many recent studies have revealed, unreflexively outsourcing one’s thinking to AI can lead to rapid deskilling and a loss of critical decision-making skills.
For my website redesign, I needed a way to decide when to do things myself, when to leverage AI, and when to bring in human expertise.
Four questions to guide any project
So how did I decide what to tackle myself and what to hand off? To navigate this new terrain, I distilled my thinking into four guiding questions:
1. Is this task central to the organizational mission?
If yes, do it yourself or invest the time in learning how. Otherwise, consider leveraging external help and/or AI.
Since I will continue to revise and update my website, I consulted with a product manager friend to learn some general principles and get feedback on work in progress. Yet because web design is not among my core services, I let AI do the heavy lifting on the purely technical and design-related tasks, from coding to color selection.
2. Do you have the time to do it right now?
If time is scarce, be ready to pay for a solution, whether an external consultant or premium tool. If time is available, do it yourself
I was fortunate to have a window in late August to rebuild my website, but I needed to finish all work by early September. I therefore sought solutions that would save time on skills I had no interest in developing myself: for example, if I was unhappy with the appearance of a web page, I ran screenshots through AI, which helped troubleshoot and provide new code.
3.Will mastering the skill create future value?
If there is high future value, invest in training or coaching. If low future value, treat it as a one-off purchase, outsource, or hand off to AI
I invested just enough time into the website creation that I would be able to coach other clients through the process. But I didn’t put time into any advanced training. If I couldn’t find a solution to a one-off problem within five minutes, I leveraged both human and AI-based technical support.
4. Is spending money on the services worth the cost?
If the answer is yes, move forward with the purchase. If no, pursue a free or lower-cost alternative.
(Stay tuned for my next newsletter, where I’ll dive deeper into evaluating the cost‑benefit of premium tools and services versus free alternatives.)
In my case, I found that I was spending too much time manually adjusting design elements, and I wasn’t always happy with the results. I finally decided to purchase a child theme to my WordPress site—a modest expense that paid for itself in saved hours.
Final thoughts
Whenever you face a new project, run through these four questions. The answers will help you invest your time, talent, and budget where they’ll create the greatest impact. In the end, you’ll have a clear sense of when it’s worth doing something yourself, when you need to leverage human support, and when you can let AI do the heavy lifting.