In my consulting work with companies and 1:1, I can be pretty directive at times (when it's appropriate). 

For example, one client with a major website does not have any sort of autoresponder to communicate with the THOUSANDS of opt-ins they get each month. 

It's easy for me to say to their team, "THOU SHALT HAVE A DRIP."

When it comes to a CEO's latest product or service, I present clear cut metrics that support my opinion. "THOU SHALT PRICE IT AT $40,000." 

In my own business and life, however, it can be much more challenging to make clearcut decisions and then move forward without any second-guessing and/or angst.

My hubs would say that I make decisions like this: 

"YES!"

"Uh, no."

"Maybe..."

"YES!"

Fortunately I did NOT go through that when he asked me to marry him! 

But I did follow that pattern for moving to NYC from VA to be with him and during many a vacation planning discussion.

You see, I am a Yes person in general. Nearly all invitations, events, restaurants, business ideas are viable options for me. And yet, saying yes to absolutely everything probably isn't in my (or others') best interest.

Still, it can be tough to come down on one side or another and say, "THIS is the direction I'm taking, all other opinions be damned."

So as I've been watching my business morph over the past few years, I've started to see how second-guessing myself hurts both the process and the outcome. I've also started to see ways to get out from under debilitating doubts to move forward on projects that I know have merit.

To give you an example of serious second-guessing, I'll share last week's experience. 

Someone suggested that I host an event for CEOs in June where I get to talk about my own IP and walk them through some exercises in real time, all while having a lovely breakfast (at the ungodly hour of 8:30 am). 

My second-guessing was like this: Can I do it in time? Can I pull this off? What if no one comes? I'm not ready. How much will this cost? I'm freaking ouuuuuuuut! 

Now, if you don't know me superwell, you might not know that I throw a fabulous party, put a high degree of emphasis on small details and overall want to create a memorable and fabulous Event. 

I also have done this more than once. 

So my second-guessing was interesting to me. 

The second-guessing doubts could have been: "I'm afraid to expand and do something new that will challenge me."

Or the doubts could have been, "This might not be in the cards right now for a host of reasons so how can I achieve the same desired outcome in a different way?"

Or even a combo of the two. 

Which brings me to my first tool.

 

1. All second-guessing is not created equal.

Some of it is there to protect us from imaginary beasties because it's so darn easier to stay small and comfortable. (That's the bad kind of second-guessing.) 

Or it could be in the form of healthy doubts that steer us towards different timing or a different route (or both). 

For me, the party planning helped me see another way to reach out to these folks without dropping $5k on a party right now as well as give me a better view on what I'd like to do down the road: a really nice event when I have plenty of time, won't feel stressed about the timeline or the money, and won't have to share the mic with a co-sponsor.

So, when you feel the second-guessing coming on, see if you can discern between the healthy kind and the "I'm putting Baby in a corner" kind.

 

2. Motivation is mandatory. 

Another important facet of understanding and using your second-guessing to grow in your discernment is to clue in to your intentions.

Simon Sinek speaks eloquently about your WHY. Why are you doing something?

Once you understand your flavor of second-guessing it becomes important to examine why you want to do something.

Last summer I went out on a limb (financially, creatively, time-wise) and created a beautiful brand and concept for a new media outlet. From the outside it looked like a viable business model. 

But it didn't work. 

Why? Because I ultimately made the decision to pursue it because of cash flow. As in, I thought it'd bring me a lot of money fast. 

And it didn't. So I pulled the plug. And I moved back into my sweet spot: a combination of work that combines my unique talents and gifts with great rates. 

I KNOW that I'm not primarily motivated by money and status (though sustainability and beautiful things are important to me). 

So anytime I chuck my instincts and try to do something JUST TO MAKE MONEY, it flops. 

Seriously. For me to be successful, I need to be engaged, challenged, and excited. 

Motivation is mandatory. 

My motivation must come from that engaged, challenged and excited place or else it just won't work. 

So next time you embark on a new project and it sort of doesn't work...ask yourself why. 

 

2. Only you know the right path for yourself. 

Now, I'm going to assume that you have a team of advisors- whether they are your C-suite or your board or your mom or your brother (I call my bro my "consigliere"). 

And I think it's fabulous to have people around whom you trust and who can offer experience, wisdom, a different perspective. 

And yet. 

Only you know the right path for YOU!

It's true. Take all their experience, wisdom and advice on board and then...do what you feel you need to do. 

I give my CEOs advice that is serious. It's about their products and services, who to hire and fire. I don't take that role lightly. They pay me well for my opinion. 

But at the end of the day, the good ones do what I tell them to do. 

Hahahaha no. (Well, mostly.) A leader has to make the final call. 

And you're the leader of your life, your business. 

You must make the call. And own it. 

***

A little detour: What separates a good leader from a bad leader is this:

A good leader makes the call. When it's proven to be successful, she shares the glory. If it goes downhill, she takes responsibility.

A bad leader does the opposite- but that's a different post!

***
Get it? You can listen all you want to advice from others, but you have to live with the outcomes. It's kinda the same with raising kids I think. Everyone has a different perspective and can share their stories, but you are the one living every day with your decisions. 

So how do you clue in to your path? 

 

4. Get quiet. Contemplate.

It's become really trendy to meditate these days. Everyone's doing it! Pro athletes, investors, Arianna Huffington and her THRIVE community. 

And it's a fabulous trend that I hope doesn't go away. 

Creating a contemplative practice for yourself (and maybe for your teams) could be one of the best decisions you ever make. 

No second-guessing here. Mountains of research prove that meditation has all kinds of tangible benefits.

In fact, I'm speaking about how to incorporate contemplative practices into your work life at SXSW Vision2Venture in July.

But really, the sometimes the loudness of the outside world drowns out our inner knowing and all it takes is dropping back in to silence and peace for us to reconnect with what we already know instinctively. 

What do you second-guess yourself about? 

And what do you do to deal with that doubt? 

 

 

 

 

 

 

 

 

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