Self Help

All The Strategizing You’re Doing Is Sabotaging Your Success

Strategizing is severely overrated. When you’re strategizing, you are paving a path of the best intentions. When you are deep in strategizing mode, everything feels exciting and doable and filled with possibility. But actually starting and following through with your best laid plans is often a completely different story. Unfortunately, far too many dreams and good intentions never proceed beyond the initial strategy stage. And for ambitious people like you and I, that is simply not good enough.

Here are 3 insidious ways that all that strategizing you’re doing is actually sabotaging your success, and most importantly, what to do instead:

1. It keeps you on the wrong side of the starting line.

We’ve been conditioned to be perfectionists. And as perfectionists, we like to wait until we have an entire plan mapped out before we get started to ensure our efforts will succeed right out of the gate. This is why shopping around for a proven strategy for what we want to accomplish is so enticing. If someone has already figured out how to do the thing, then all we have to do is copy their strategy, and voila! Success.

I once heard Mel Robbins say that perfectionism is not really the pursuit to be perfect, but rather “the desire to be immune from criticism.” (Doesn’t that just hit you right between the eyeballs?) You’re not spending all this time in strategy mode just because you think it’s the smart thing to do. You are lingering here because it’s far more comfortable on this side of the starting line. It’s safer here. You can’t fail or get rejected or make a mistake before you cross the proverbial starting line. So the longer you avoid crossing that starting line, the longer you get to remain “immune from criticism.” If you want to achieve anything that matters to you, you have to get into implementation mode even before you have everything ready and “just so.” The truth is, it’s never going to be perfect. You just have to go for it.

2. It gives you a false sense of accomplishment.

Building out a fancy-pants strategy can give you a false sense of accomplishment. You can spend countless hours creating whimsical mind maps and spreadsheets filled with brilliant ideas and logical steps connected by arrows and timelines. You can spend loads of time talking through business models or process ideas with other strategy junkies, exploring endless possibilities. Or you can find yourself endlessly shopping for someone else’s step-by-step strategy for making things happen instead of actually making things happen. 

When it comes to goals, it’s all about taking action. At the end of the day, you can have the best laid plans in your hand, but if you haven’t taken any steps toward their execution, you’re still no closer. In fact, you’ve lost yet another day to strategizing when you could have been implementing all along.

3. It promises more than it can deliver.

By definition, choosing a strategy assumes that if you follow a series of steps, you are guaranteed a desired outcome. So if you can just find and adopt the right strategy (whatever that means) and then follow the outlined steps with fidelity, you should expect to get the same results. 

It totally makes sense that you want to find a solid strategy for your next big endeavor. Why reinvent the wheel when someone else out there has already made mistakes, course corrected, and lived to tell the tale? If you can get your hands on someone else’s recipe for success, shouldn’t you shorten your learning curve by benefiting from their lessons learned? 

Right? Yeah, not so much. Not in my experience, anyway.

Internet marketers everywhere are hip to the fact that we crave clever shortcuts to success. They craft carefully worded sales pages promising to share the secrets to their success path in a tight, eight module package of videos and workbooks. If you act now and just adhere to their roadmap, you too can be as rich and famous as they are by next Tuesday. 

I get it. That sounds really good on paper. I’ve bought plenty of that same infocrack myself, much of which is currently collecting cyber-dust on my desktop right now. But none of those prepackaged strategies can take into account our unique needs, strengths, and goals. All these programs tend to do is cost us more time, money, and confidence than we can afford.

For ambitious people who want to do great things in this world as soon as humanly possible, following someone else’s step-by-step is never going to cut it. Your success path is uniquely yours. So borrow some of those great ideas, sure, but ultimately, you’ve got to blaze your own path. 

“Strategy is a fancy word for coming up with a long-term plan and putting it into action.” – Ellie Pidot

So now what?

You know that the quicker you implement, the faster you will move the needle toward what you want to accomplish. Ultimately, what really matters is the final outcome, not a six-month process of coming up with a plan. But implementation only happens after you let go of the perfectionism of take that big, scary step off the starting line paint. So how on earth can you move past the safety of strategizing mode and starting making things happen?

Approach everything as an experiment

But what if instead of waiting until you feel “ready,” you went ahead and started doing the thing? What if instead of just planning, or waiting until everything is just so, or until the stars align in a way that’s convenient for you, you jumped into implementation mode? Instead of spending another day strategizing (or shopping for someone else’s prepackaged strategy), consider approaching your next big thing as an experiment. And be clear: I’m not talking about some super sophisticated A/B split testing sort of project; I suggest tackling your next big thing as you would a fourth grade science experiment. 

A strategy requires you to map out all the steps and predict all the possible challenges before you get started to achieve a specific end. But by contrast, our fourth grade experiment sets out to test an educated guess. Identify or predict what you think might happen (your hypothesis), even though you can’t be sure how things will actually go down. But now you can get started, try some things out, collect a little data, and see what happens. 

When you approach your goals as experiments, all that self-sabotaging perfectionism and procrastination is instantly squashed. You can start immediately – even before you have everything figured out – because you’ve given yourself permission to just start and trust that you’ll figure things out along the way. Each day in your experiment, you experience a much richer sense of accomplishment, because you’re learning whilst taking bold, imperfect action. You’ll stop looking to gurus to have all the answers and trust yourself to find your path, your way. And most importantly, you’ll get much farther, faster than you ever did strategizing.


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