Sometimes the interviewer asks a question that is very common. I hate this question, and you probably do too. Five years ago, if you had asked me where I would be today, I might have said something like “Running a cozy coffee shop” or “VP of Sales at a tech unicorn.”
The truth is? Life doesn’t care much about your Google Calendar. Businesses combine, industries die (RIP to half the jobs we thought were safe in 2020), and you change.
But here’s the catch: Not being able to see the future doesn’t mean you shouldn’t plan for it. If you don’t have a plan, you are like a leaf blowing in the wind. You move from job to job, taking the one that pays $5,000 more, until you wake up at 40 and realize you’ve been climbing a ladder that was leaning against the wrong wall.
A real 5-Year Plan isn’t a list of things you want. It’s a plan for war. It means knowing that the battlefield will change, but also knowing exactly which hill you want to take.
This is how to make a career plan that will work in the crazy world of 2026.
1. Anti-Vision
A lot of people start with positive visualization. “I want an office in the corner. I want a Tesla. I want to be in charge of a group.”
The problem is that we are very bad at figuring out what will make us happy. But we are very good at knowing what makes us unhappy.
So, begin with the Anti-Vision. Write down everything you don’t want your life to be like in five years on a piece of paper.
- I don’t want to drive for two hours every day.
- I don’t want to work on the weekends.
- I don’t want to work for a micromanager.
- I don’t want to be poor.
This is the guardrail for you. If someone offers you a job that pays a lot of money and requires a two-hour commute, you should say no. Why? It goes against the Anti-Vision. It’s more important to know what to say “No” to than what to say “Yes” to.
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2. Stop Chasing Titles, Start Stacking Skills
A title is a sign of pride. A skill is fairness. You are setting yourself up for failure if your five-year goal is to “Become a Senior Director.” Someone else has to promote you to get that title. It all depends on how things are done at work.
Plan for a Skill Stack instead. The idea came from Scott Adams, who is the creator of Dilbert. You don’t have to be the best coder in the world to be good at something else. You only need to be in the top 25% of two or three things that aren’t related to each other.
- Example Strategy:
- Year 1-2: Get in the top 25% of people who can do data analysis (the technical base).
- In years 3 and 4, you should be in the top 25% of people who can speak in public and communicate well.
- Year 5: Put them together.
You are now more than just a “Data Analyst.” You are the “Guy who can explain complicated data to the CEO without putting him to sleep.” That guy makes twice as much as the pure analyst. Plan the next five years of your life based on what you will learn, not what you will be called.
3. “2 + 2 + 1” Framework
Five years is too long to make detailed plans. The technology changes too quickly. Make it a flexible framework: 1 year of risk, 2 years of depth, and 2 years of breadth.
- Years 1–2 (Depth): This is the hard work phase. Choose a niche. Go deep. Get the certificates. Put in the long hours. Be the person that everyone goes to for that thing. You are laying the groundwork.
- Years 3–4 (Breadth): Look up. Start taking care of people. Learn how the other departments do their jobs. Change from “doing the thing” to “understanding the business of the thing.”
- Year 5 (Risk): This is your year to swing. Because you spent 4 years building skills and connections, you now have a safety net. This is the year you start your own business, ask for a huge raise, or switch fields completely. You can afford to take a chance because you have four years of solid equity.
4. Network Like a Farmer, Not a Hunter
People network like hunters do. They need a job, so they go out and look for people to connect with. They send LinkedIn messages that are spammy. They ask for help right away. This is disgusting and it doesn’t work.
You have to farm. Set aside one hour a week in your five-year plan for “Watering the crops.”
- Send an email to an old boss saying “I’m thinking of you.”
- Congratulate a coworker on their new job without asking for anything in return.
- Put something useful on LinkedIn.
If you do this for five years, you’ll have a huge orchard of relationships ready to pick. You won’t have to look for jobs when you turn five and want to make a big change. You will get offers after making three phone calls.
5. Freedom Fund Financial Strategy
If you live paycheck to paycheck, you can’t have a bold career. You will never take the risks you need to grow if you are afraid of losing your job. You will stay in the safe, toxic lane because you need the money.
A financial plan must be part of your career plan. You should try to save up enough money in the next five years to start a “F* You” Fund.** This is cash that can cover living costs for 6 to 12 months.
When you have this money in the bank, you have a lot more power in negotiations.
- Your boss treats you like dirt? You can leave.
- The job offer is too low? You have the right to say no.
- Want to take a break from work? You can do it.
Having money gives you the freedom to make career choices based on growth instead of fear.
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6. Annual
This is the tough part. Every December, sit down with your plan and be ready to throw it away.
You might have wanted to be a graphic designer, but AI image generators have made it almost impossible to get a job at that level. Just because you wrote down a plan doesn’t mean you have to stick to it. The “Sunk Cost Fallacy” is what that means.
If the market changes, move right away.
- “Okay, design without any other elements is dead. I’m changing my approach to “AI Design Operations” or “Brand Strategy.”
The goal is not to follow the map exactly; the goal is to get to the end (a happy, wealthy life). Look for another way if the bridge is closed.
People who make 5-year plans often make the mistake of thinking too much. They spend months worrying about the best way to go.
Final Thoughts
Doing something gives you information. In one month of actually working, you’ll learn more about your career than you will in a year of planning. Make a rough copy. Choose a way. Get going. You can always steer a car that is moving, but you can’t steer one that is parked.
FAQs
Q: My field changes every six months (AI, Tech). Is a plan for five years really useless?
A: Yes, it’s useless if your goal is to be a React Developer by 2030. By then, AI might be able to write React code. That won’t change if your goal is “I want to be a leader in Technical Product Strategy.” Think about the role you want to play and the problem you want to solve, not the tool you use right now. The tools change, but the problems (making money and saving time) stay the same.
Q: The “Anti-Vision” sounds sad. Shouldn’t I make good things happen?
A: Positive thinking is good, but it can be hard to understand. “I want to be rich” is a weak goal. A clear rule is “I won’t work for a boss who calls me on weekends.” Pain is a stronger reason to do something than pleasure. When you say what you hate, you make a clear line that keeps you from taking the wrong job just because it pays well.
Q: I’m 45. Is it too late to make a plan for the next five years?
A: Figure it out. You will probably work until you are 65 or 70. You have 20 to 25 years left. That’s four or five different “5-Year Plans.” You haven’t finished yet; you’re only halfway there. You are actually in a better place because you already know what you don’t like (see the Anti-Vision).
Q: How can I “stack skills” if I don’t have time to study after work?
You don’t study after work; you learn while you work. Sign up for the project that scares you. Offer to run the weekly meeting if you need to learn how to speak in front of a group. If you need to learn about data, ask the data team if you can follow them around for an hour. Learn and get paid. You will get tired of learning if you only do it in your free time.
Q: What if I set up a “Freedom Fund” and then an emergency wipes it out?
A: The fund did what it was supposed to do. It kept you from going broke. You begin again. It stinks, but it’s better than the other option. The fund’s goal isn’t just to sit there forever; it’s to help you say “No” to bad bosses without worrying about money. Having even one month’s worth of expenses saved can change how you act in a negotiation.
