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Improve Results By Second Guessing Yourself

Mar 20, 2025

What if second guessing yourself was the secret to success?

I did a quick search on second guessing, and I wasn’t surprised by the results:

 I’ve always been told not to second guess myself, to trust my gut or trust my instincts, and to quit thinking so much.

Second guessing has a bad reputation, but maybe it’s not so bad after all, but only if you’re second guessing the right things.

Second guessing the wrong things can keep you stuck for years, never really taking action.

Second guessing the right things can challenge your assumptions and allow you to accomplish things you weren’t previously able to.

What a pickleball serve taught me about second guessing

The other night I was playing pickleball with my wife.

We were just hitting the ball around while our kids ran around otherwise empty courts.

Being 30+ weeks pregnant, she hadn’t been playing anytime recently, and it had been some time since we even hit the ball around.

I had recently been playing more often, but I was struggling badly with the consistency of my serve.

I just couldn’t get it to feel right, and it was honestly about 50/50 if I could just get it in play, and that was on a good day.

I wasn’t trying some fancy serve, I was just trying to be more consistent.

It was definitely the weakest part of my game.

I served a few to my wife, feeling bad that I was making her move a little more than she probably wanted to being that pregnant.

It wasn’t on purpose, I just couldn’t get my accuracy down.

Getting frustrated with myself, I told her to serve a few and let me do all the running.

Well first off, to no surprise of mine, her serves were great even after barely playing for years.

She’s naturally a great athlete.

Whether she was actually curious, or just entertaining me to make me feel good after a few perfect serves, she asked, ‘wait am I supposed to bounce the ball first or hit it out of the air?’

I told her most people don’t bounce it, and it was more effective to hit a volley serve right out of her hand instead of dropping it.

I assumed this to be true, because 90% of the people I played against - and certainly the better players I played against - almost exclusively used a volley serve, and not a drop serve.

Wanting to show her why it was less effective, I decided to hit one back as a drop serve.

I hit a great serve that landed right in the middle of her side.

‘Let me try that again’ I said, thinking it might have been a fluke.

Another great serve. And another. And another.

The kids were getting antsy, so it was time to head back, but out of the 10-15 serves I hit - I probably only missed one.

My results were instantly 40-50% improved.

What assumptions, beliefs, or stories do you have that are holding you back from a significant breakthrough?

I would have taken a 10% improvement, but one simple change led to massive improvements.

Thinking back on it, I wondered why I hadn’t tried serving like that any sooner. Here were a few things that came to mind:

  • I equated the drop serve to the underhand volleyball serve. If you know what I’m talking about, you know that’s a sign of weakness for men (pride, worry about what other people would think).
  • I believed it to be an inferior serve, as most people I observed didn’t serve that way (not having all the information, false assumptions).
  • I was so focused on fixing the current way, instead of finding a new or better way (stubbornness, close minded or fixed mindset)

While pickleball might seem like a trivial example, for someone who is an average recreational player, here’s one that might be more relatable.

For years I internally convinced myself I could never get ‘that’ lean. 

Your definition of ‘that’ lean/fit/muscular is going to be different than mine, but maybe you’ve told yourself that before.

  • My genetics aren’t great
  • My metabolism is slow
  • My hormones aren’t great
  • I don’t have time to workout like that/eat like that
  • Must be nice that it’s their job to be healthy
  • I’m too old

The list can get long in a hurry.

I justified my lack of results over my metabolism, too much stress in my life, my gut health, and whatever I could.

I was trying to provide meaning as to why I couldn’t get results, yet I was only exaggerating the problem by making excuses or avoiding finding a different path.

I was forcing a volley serve when I could have drop served.

Once I challenged the more is better mentality, and shifted my mindset, everything started to change.

I dropped under 10% body fat in the matter of 4 months - a goal that I had failed at for years.

Second guessing has it’s dangers, but it has it’s superpowers as well.

There’s always a dark side and a healthy side.

The answer is certainly not to second guess everything.

There are some of you that just need to make up your mind and start taking action.

You’re plagued by inaction, indecision, and excuses - just like I was for over a decade.

It’s important to understand that second guessing and indecision are not synonymous.

Second guessing is not an excuse to not take action.

Indecision is procrastination. It’s fear. It’s inaction. It’s a false belief that more information will get you more results.

Second guessing is shining the light on the things you might not see clearly.

It’s having the wisdom to ask for help or to question if there are any other ways.

Sometimes that’s having someone say ‘just go for it’ when you’re stalling or delaying.

My wife is great at this.

She ‘encourages’ me when I start going down a loop of overthinking thoughts.

Sometimes it’s having someone say ‘I know you think you’re doing the right thing, but have you thought about ___?’

You can be so convinced that you’re doing the right thing. As humans we’re great at justifying why we should or shouldn’t be doing something.

That doesn’t mean it’s true.

If you never second guess why you’re doing something, here’s where you’ll end up.

  • You’ll get the same results you’ve always gotten
  • You’ll make some forward progress, but you’ll get slower results
  • You might end up with even worse results

Getting 2x, 5x, 10x, or 100x results can’t happen without second guessing.

To practice the right way of second guessing, here are some questions that can help:

  • Who is doing what I want to be doing? Tony Robbins has said that ‘success leaves clues’. There are people you know, or people you can study, that are doing exactly what you want to be doing. Listen to what they say, without putting your own biases or judgment on their advice. More importantly, watch what they do.
  • What don’t (or can’t) I see? To reach new levels of success, in any area of your life, you have to be open to the fact that you don’t have all the answers. By pausing to think about this - or better yet ask someone who is already doing what you want to be doing - you can see new possibilities and ways of doing things.
  • How can I ____ so that I ____? This type of question can challenge your own thinking. Asking yourself ‘Why am I overweight?’ or ‘Why can’t I gain more muscle?’ won’t lead to productive solutions. Instead, asking ‘How can I lose 20 lbs in the next 6 months so that I can fit into my clothes better and have more energy?’ will lead you to different (and more specific) solutions.

If you find yourself stalling on taking action - start questioning what’s behind your indecision. For me it was fear, pride, and a lack of accountability.

If you’re trying hard - but barely seeing progress - try second guessing what you’re doing. Ask for help. Be open to change.

You’ll be surprised what breakthrough is on the other side of that.

Dave

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