You’re stuck in a tough spot. You see AI rapidly changing the tech world. You know that to get your next big job—especially if you want to be a VP or a C-suite leader—you need new skills. You need to know how to lead with AI.
But right now? You’re buried in work. You have endless meetings, emails, and daily fires to put out. You have big goals to pivot into AI leadership, but you have zero free time. You feel like you have to choose: do a good job today or prepare for your future.
Getting Left Behind
The problem isn’t just that you might miss out on the fun; it’s that you might get left behind. While you’re busy managing old workflows, other people are learning how to use AI to do things faster and better.
If you wait for your company to give you a formal “AI Training Class,” you’ll be waiting too long. But trying to learn AI late at night or on weekends is a recipe for burnout. You can’t keep living a double life—employee by day, student by night. It’s exhausting, and quite honestly, it doesn’t work.
The Strategic Side Project
The answer is to stop separating “work” from “learning.” You don’t need to quit your job to learn AI. You don’t need to give up your weekends. You need a Strategic AI Side Project.
This isn’t about making a fun app or game. It’s about finding a problem at your current job and building an AI tool to fix it. When you make your learning help your company, it isn’t a distraction anymore. It’s “Research and Development.” You get paid to learn, and you build a real example for your resume that proves you can solve business problems with AI.
How to Make It Work
To do this right, focus on 3 simple ideas:
1. Alignment Is Key: Your project needs to help you and your boss. If you work in finance but you build an AI art generator, your boss will think you’re wasting time.
- The Strategy: Pick a boring, slow, or expensive problem your team faces every day.
- The Result: Your boss sees you as proactive. They see the project as both work and “professional development”. You get to learn AI skills during work hours because you’re solving a work problem.
2. Task vs. Strategy (Thinking Like a Boss): A big mistake people make is using AI just to do more work.
- The Shift: Don’t use AI just to write code faster. Use it to get the boring tasks off your plate.
- The Goal: If you spend 10 hours a week writing summaries or fixing data, build an AI agent to do it for you.
- The Payoff: This frees up your brain. While the AI handles the “grunt work,” you can focus on big-picture strategy. This is how you demonstrate you’re ready for the next level—by showing you can manage resources to get things done, rather than just working harder.
3. The “Shadow” Portfolio: Write down what you do. The code you write to fix that report isn’t just a script; it’s proof of your skills.
- The Tactic: Keep a simple log. Write down the problem, how you used AI to fix it, and the result (like “Saved the team 15 hours a week”). This is what you’ll talk about in your next performance review or job interview.
Start Your Stealth Project
Stop treating AI like a school subject. Pick one annoying thing in your week—a report, a messy spreadsheet, a recurring email—and fix it with AI.
Tell your manager: “I’m testing a new AI tool that could do this task automatically and save us time. I’m going to spend a few hours setting it up.”
Now, you aren’t distracted. You’re innovating. You’re building your next job, right in the middle of your current one.
Advice for Tech Leaders
If you manage engineers or product managers who are playing with AI, don’t stop them.
- Give Permission: Let them know it’s okay to use a little work time to experiment, as long as it helps the business.
- Share the Wins: If someone automates a boring task, let them show the team. It’ll boost morale.
- Change Your View: Don’t look at this as “lost time.” Look at it as training for your team that improves internal processes.
Notes From Drew
If you want to actually do this, here is your homework:
- The Time Audit: Write down what you do and find a boring task that happens all the time. This is your target.
- The “Good Enough” Tool: Don’t try to build perfect software. Use a simple tool like ChatGPT, Claude, or Gemini to fix that one specific task.
- The Reveal: Once it works, show your boss the result, not the code. Say, “Here’s that analysis you wanted. I built a tool to create this automatically from now on.”
- The Resume Update: Add this to your resume or LinkedIn. eg, “Built internal AI tools to cut reporting time 40%”.
Build the skill. Automate the chore. Get the promotion.
