Have you ever spent hours, days, or even months planning something, only to realize you haven’t started, or if you have, you haven’t done all that much? Maybe you have a dozen notebooks filled with ideas, A Word or Google doc of tasks, or a list of goals so long and detailed that it feels overwhelming to look at it. If you do, you’re not alone. Overthinking and overplanning often disguise themselves as productivity, but they’re actually just mental roadblocks. They create the illusion of progress while keeping us stuck in the same place. And yes, I am writing from experience. The real challenge isn’t coming up with ideas—it’s executing them. So, how do we get unstuck? How do we break free from analysis paralysis and take meaningful action?
One of the biggest traps of overthinking is wanting to do too many things. You might have ten different goals, all equally important in your mind. You may want to start a new business, write four books, lose 60 pounds or more no matter how old you are, travel, relocate to a warmer and sunnier climate, and learn a new language, all at the same time. But trying to do everything at once leads to decision fatigue, frustration, and ultimately, inaction. Instead of spreading yourself thin, prioritize. What’s the one thing that matters most right now? Not forever; just right now. Ask yourself: What will impact my life most if I start today? What is truly urgent, and what can wait? What excites me the most? Choose one primary focus, and let the rest sit on the back burner. Once you gain momentum, you can tackle other goals.
The problem with overplanning is that it makes things feel bigger than they are. A goal like “write a book” or “start a business” can feel massive and impossible. Instead of looking at the entire mountain, take the first step. Set a rule: Break every goal into the smallest possible action you can take today.
Momentum builds from small wins yet the hardest part is often just starting.
Planning is proper, but only if it leads to action. If you find yourself constantly refining your plan, researching endlessly, or waiting for the “perfect moment,” set a time limit. Decide: I will spend no more than [X] hours planning before taking action. Give yourself one week to research a project and then start. Allow 30 minutes to plan your day and then execute. Spend one hour outlining your book and then write the first page. The key is to make planning a tool, not a crutch.
One of the biggest reasons people get stuck in overthinking is the fear of failure. What if it doesn’t work? What if it’s not good enough? What if people judge me? Nothing will be perfect on the first try. No book is flawless in the first draft or even the fourth. No business launches without hiccups. No fitness journey is mistake-free. You’ll never start if you wait until you have all the answers. Take sloppy, imperfect action. Learn as you go. The faster you start, the quicker you can adjust and improve.
Most people set outcome-based goals, like: “I want to lose 50 pounds.” “I want to write a best-selling book.” “I want to make $120K this year.” However, outcome-based goals don’t tell you what to do today. Instead, set execution-based goals: Instead of “lose 60 pounds,” → “I will eat less, and exercise for 30 minutes daily.” Instead of “write a book, → “I will write 500 words every morning.” Instead of “make $120K, → “I will pitch three clients per week.” Execution-based goals give you control. You can’t control the outcome, but you can control your effort.
It’s easy to procrastinate when no one is watching; the antidote to this is to create accountability: Find an accountability partner who will check in with you. Announce your goal publicly– Social (media) pressure can be motivating, but remember not to overdo it. Use a habit tracker; seeing your progress visually can keep you going. When others expect you to follow through, you’re less likely to make excuses.
Overthinkers tend to say, “I’ll start tomorrow” or “next Monday will be better.” But waiting doesn’t make things easier. Yesterday was the best time to start, and now is the second-best time. When you catch yourself hesitating, ask: “What small action can I take in the next five minutes?” “If I had to start right now, what would I do first?” “What’s stopping me from taking action today?” More often than not, the answer is simple: nothing but fear or perfectionism. You don’t need the perfect plan; you just need to start and take it one day at a time. What’s one small step you can take right now?
John Berkovich Talks 