How Over Planning May Actually Destroy Your Successful Career
Leave room for serendipity. Steve Jobs and I have something in common.

The career experts all trumpet the value of having a plan. Have a yearly plan, a 5-year plan, and a 10-year plan. Know where you’re going, so you know how to get there.
Yet look at any successful person, and you’ll find a history littered with happy accidents and failed plans.
Steve Jobs bought Pixar for their Pixar Image Computer (PIC), an early graphics computer built for the Lucasfilm Computer Division. Despite the superiority of the graphics processing, they sold very few units. But the animated movies the company turned out using the PIC made Jobs a billionaire after Pixar went public. And working with Pixar changed his management style, so when he came back to Apple, he was able to transform the company into the success it is now.
If he had been rigidly committed to a plan, he would have struggled to make his NeXT computer profitable. He would have been so focused on that, he wouldn’t have considered what the computer designers were doing for Lucasfilm. He’d have ended up a footnote to the history of computer design.
Serendipity can upgrade your plans
The new-age idea of manifestation made popular by The Secret has a kernel of truth to it, as most things do. It’s impossible for us to comprehend all of the billions of random actions that can create opportunities leading to our goals. We can’t plan for them. We can, however, make sure to capitalize on them when they occur.
For example, I had a successful 22-year career with IBM. But it came about as a result of two serendipitous accidents.
Two serendipitous opportunities
The first happened while I was still in school. I’d had a co-op job with IBM Owego (NY) during my junior year of college. Somehow, two years later, I got a summer job offer from IBM Endicott (about 13 miles down the road from Owego), for a job I never applied for.
I loved the job, and I loved the people I worked with. But I planned on going back to school to finish my PhD at the end of the summer. Instead, one of the other departments in my organization had an external hire chit that was about to expire. The head of the organization asked if any managers had someone they could hire in under a week, and my manager raised her hand.
Serendipity versus planning
I could have refused the offer of a summer job. It hadn’t been part of my plan. I hadn’t even known that they were looking for someone for that position.
I could have refused the offer of a full-time job. I had a full fellowship waiting for me. I had a plan to complete my PhD, then go into research.
But when serendipity put these opportunities in my path, I grabbed them. Just like Steve Jobs didn’t stay focused on his plan for the NeXT computer when the opportunity to buy the PIC came along. And then he took advantage of the success of Toy Story for Pixar’s Initial Public Offering.
You can’t plan for serendipity. But you can take advantage of it when it comes.
Key takeaway: If a serendipitous opportunity comes along, be willing to change your plan to take advantage of it.
Serendipity can derail your plans
My story and Steve Jobs’ both proved the advantages that can come from scrapping a plan and grabbing hold of a serendipitous opportunity instead. But many people scrap perfectly good plans to chase opportunities that never go anywhere. They don’t get what they were originally after, but they don’t get what the opportunity promised, either.
Testing for Shiny Object Syndrome
A lot of times, these people fall prey to the Shiny Object Syndrome. They never stick with anything long enough for it to be successful, because they are always on to the next shining promise. You can ask yourself these three questions to make sure you’re chasing a real opportunity, not a shiny object.
Another question to ask yourself is if the new opportunity supports your end goal or not. For example, if your goal is to sell computers, buying a computer company that manufactures the best graphic processing computers currently available could be a route to accomplishing that. Creating a movie wasn’t something that supported Steve Jobs’ end goal. The only reason he didn’t get rid of the Pixar animation studios side of things was because his business was desperate for cash, and they signed a deal to animate movies for Disney.
You can circle back around to opportunities
He didn’t get involved in the movie, but when it was clear they had something special on their hands, he took advantage of it. He’s the one who tied Pixar’s IPO to the release of Toy Story. He allowed a couple of weeks of buzz in the industry before giving people an opportunity to buy into this phenomenon. Because a successful IPO did tie into his end goals.
Key takeaway: Only follow a new opportunity if it supports your goals, not replaces them.
Conclusion
Don’t try to over plan your life. You can’t control everything, and insisting on a particular way that your life must roll out will only make it harder for you to achieve your goals.
Instead, leave room for serendipity. These chance encounters, experiences, and interactions can jump your life forward. They can also change your goals, or prevent you from ever reaching your goals, if you grab every opportunity indiscriminately.
Test potential opportunities to see if they support your goals. If so, take full advantage of them.
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