From Thinking to Doing- How to Take Action

For a long time, I mistakenly believed that success required a detailed plan—a step-by-step roadmap to guide me from where I was to where I wanted to be. Whether it was learning a skill or chasing a goal, I felt certain that preparation was essential.

What I didn’t realize was that my need for a perfect plan was holding me back.

Without getting too much into the psychology of why I was that way, I suspect it’s related to a previous lack of confidence.

If this resonates with you or you’ve ever been stifled from action by the overwhelming desire to create the perfect plan, this blog post is for you.

Looking back, it wasn’t an improved confidence that made me pivot; it was necessity. After my divorce, I faced a reality that required me to rebuild my life and career. I couldn’t afford to wait for the “perfect moment” or the “perfect plan.” So, I stopped overthinking and started doing.

That simple shift changed everything.

The Trap of Over-Planning

For years, I believed that planning was my safety net. I thought having a clear, detailed strategy would protect me from failure. But in reality, planning became a form of procrastination. If I stayed in the planning phase, I could avoid the discomfort of trying and failing. It was a way of convincing myself that I wasn’t failing—I just hadn’t started yet.

When I began thinking about rebuilding my career, I fell into this same trap. I read every book I could find about different professions, combed through online resources, and researched endlessly. I had an inkling that writing might be a good fit for me, having had some success with business writing in the past. But I kept thinking I needed more knowledge, more preparation, and more time.

It wasn’t until I remembered a lesson I had seen my ex demonstrate that I finally took the leap. He often entered fields he knew nothing about and figured it out along the way. The audacity! I needed some of that in my own life. 😊

While I may have differed with him in many ways, I couldn’t deny that this ability to learn on the go was one of his strengths. And I realized there was no reason I couldn’t do the same.

The Power of Jumping In

One day, I decided to call myself a writer—no more waiting, no more second-guessing. From that moment, I focused on finding freelance work and building my portfolio. I worked on my own projects, refined my skills, and adjusted as I learned what worked and what didn’t.

The first few months were messy and full of uncertainty. But they were also filled with growth. I landed my first client, then a second. Repeat clients started coming back to me, which was not only satisfying but also a huge confidence boost. It felt amazing to know that people trusted my abilities enough to hire me again.

This was one of the first times I committed to “building the parachute after the jump,” and it taught me a valuable lesson: action breeds clarity and confidence. By starting before I felt ready, I learned far more than I ever could have from reading or planning alone.

When Planning Becomes Stalling

Now, I recognize that over-planning is often a signal that I’m stalling. That’s not to say planning isn’t useful (it absolutely is) but I’ve learned to keep it brief and focused. For me, the best approach is to set habits or goals once a quarter and then dive in.

I’ve applied this mindset not just to my work but also to other areas of my life. For example, when it comes to improving my health, I used to obsess over crafting the perfect 12-week plan. Now, I focus on building one habit at a time and occasionally take on short bursts of effort to see measurable progress.

Even this blog is a reflection of my shift from planning to doing. For a long time, I held back from sharing my thoughts and experiences online, thinking I needed to perfect every post before hitting publish. But I realized that finished is better than perfect. Every day I don’t share a post is another day someone who might benefit from my perspective has to wait.

Learning by Doing

If you’re hesitant to start something new, take inspiration from children. Babies don’t wait to master the theory of walking before taking their first steps—they just keep trying until they figure it out. And while adults have the advantage of learning from others, the principle remains the same. Progress comes from action.

When you pair ‘doing’ with a willingness to learn, you set yourself up for faster, more effective growth. Whether you’re pursuing a career, a personal goal, or a passion project, don’t let the fear of imperfection hold you back.

A Challenge for the Perfectionists

If you identify as a perfectionist or a perpetual planner, I’d like to challenge you.

Think about an area in your life where you could jump in without overthinking. It might feel uncomfortable at first, but it’s not as scary as you think.

Learning to handle the unexpected is a skill in itself, and it’s one that builds confidence in every area of life. The next time you find yourself stuck in the planning phase, remind yourself: the fastest way to learn is by doing.

Take the leap. Start before you’re ready. You might surprise yourself with what you’re capable of achieving.