Reskilling After AI: A 2026 Reality
If I had to start over in 2026, what would I do?
I never wanted to write about this, but AI is taking. Ignoring this fact will only make it worse.
This is why we’re not going to focus on why AI causes job loss and instead focus on what we’re going to do about it. Being jobless is hard, but 2026 can be the year everything changes for you (for the better) and reskilling might just be the answer. If it’s not the whole answer, it’s definitely going to help.
Before we talk about specific steps, let’s talk about the current job environment (as of November 2025.) As it stands, the economy feels uncertain and AI is rewriting what it means to work. To deal with this uncertainty, you need to show how you can kick ass (or you know, show value, but “kick ass” sounds better) in this new environment. To do that, you’re going to do following five things:
Step 0: Decide What You Want to Be When You Grow Up (At Least For Now)
Before you go down the path of reskilling, pause. If you’re like me, pausing is going to feel realll weird, but do it anyway. With the loss of your job, you now get to ask yourself what you really want to do. If you were a dentist before, do you still want to be a dentist now? Would you rather be a chef or a mechanic or an entrepreneur?
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There’s not a wrong path (well, maybe career criminal) as long as you take care of your family and meet your basic needs. With that said, this article is focused on office work. If you want to be an entrepreneur, there are lots of resources here for that. If you want to go into trades or become a mechanic, etc., I have all the respect for you in the world, but I suggest you look up trade skills and job retraining programs. I wish you luck, but I also don’t want to lead you astray.
Work On Your Personal Brand
Now that you know what you want to do, work on your personal brand. This is the age where a single viral tweet can cross the globe and come back again in less than a second. You want the world to know that you are looking for work and that you are completely capable of kicking ass.
For a lot of people, this may sound like a death sentence and I get that. You don’t have to become an Internet thought leader, but become part of the conversation around your chosen field. Reply to experts on social media. Ask questions. Attend free virtual conferences, etc. When you go to do an interview, you want your interviewers to know who you are.
2. Understand AI
If you don’t feel comfortable asking ChatGPT for help writing an email, answering a question, analyzing data, creating a graph, etc. start getting comfortable now. Don’t pay for any fancy courses unless you can’t help it. Instead, watch a lot of YouTube and read a lot of blogs then do what they do. Right now, your general AI skills will be a competitive advantage. Soon, they will be table stakes.
Once you have a good feel for AI, go research how it can help your chosen industry. See what advances are being made with AI. Be able to recreate them if possible or be able to talk about them confidently in an interview.
3. Be Better Than the Robots
Now, this is where the rubber meets the road. At this point, you should know about AI and what it’s doing for your industry. Now, you have to figure out how to be better than the AI. The problem is that, as it stands, even the most basic AI is better than many entry-level workers.
That’s why you need to decide how you’re going to do better than an AI. There are lots of ways to do this including going deep on a specific topic (and hopefully getting hands on experience on that topic) or showing that you are a very broad generalist in your field. This may take longer than you want, but being good at the job you’re about to get is never a bad idea.
4. Create the Proof
Finally, no matter what you decided to do in Step 3, you’re going to need proof that you’re better than the AI. In programming, that means putting a prompt library together (to show you can vibe code) and a GitHub repo together (to show you don’t need to.) If you want to be a marketer, create marketing collateral. If you want to work in an office, create masterful spreadsheets and presentations and show how quick and easy it is.
It’s not going to be easy, but ultimately, reskilling in 2026 is about making sure your skills are modern and that you can stand out. In this new market, that means having advantages over other applicants and the AI. If you can do that, you can get hired in 2026.
With this advice, what’s your biggest worry about reskilling in 2026?
