How to Become a More Daring CEO by #TheDaringCEO

Being a Daring CEO does not come naturally to me. It takes work, and it takes intention. But the best things in my business have also come from those dare-inspired actions.

I land an incredible client. I get an amazing opportunity to speak at an event. I hit it out of the park with a new offer.

Every time one of these opportunities presents themselves though I battle with the temptation to stay comfortable and put it off “until later when I’m ready.”

This was the reason why in 2016, I started doing this little thing called the CEO Dares. I created a list of things I wanted, highlighted everything that I felt too scared to do and one by one, I created a plan to tackle them.

I got a lot of no’s. I got a lot of silence.

But the yesses more than made up for any of these.

So for me this is what being a Daring CEO is all about – focusing in on something you want to be, do or have and taking small (often teeny tiny) steps to make it happen.

This is the Year of the Daring CEO

I’m declaring this year of the Daring CEO – at least for myself and for anyone who wants to join me.

Because likely you’ve been waiting long enough on the things you say you want most in your business and life.

And while I love this quote from Ann Landers, of the legendary “Ask Ann Landers” column, that says, “Opportunities are usually disguised as hard work, so most people don’t recognize them.” The thing is – it doesn’t have to be hard.

Whether or not you finally take action is binary. You either do, or you don’t. It doesn’t matter whether you take the “rip the band-aid off” off approach with big, massive action or the itsy-bitsy lean-into-it approach with small steps forward.

All action is progress, and it’s the habit of the Daring CEO that I’m aiming to cultivate this year.

Plus, to get a little sentimental on you, 2019 is the last year of this decade, so I think we should all finish this one off having taken a chance on ourselves, our ideas and desires 😛

If you want company and accountability in your CEO Dare journey – you have an open invitation to my CEO Dare Roadmap – a FREE 5-Day Email Course guiding you through choosing, planning and tackling your first CEO Dare. Just click here to sign up!

Download the CEO Dare Roadmap by #DaringCEO

But for now – here are 10 easy steps that you can take to start cultivating your daring CEO habit right now!

Here are 10 easy steps to flex your “CEO dare muscle.”

Step 1: Make your CEO Dare list

My journey with CEO Dares began with that fateful list of everything I wanted to be, do, and have in business.

It included things like…

  • Host my first webinar (I am way too embarrassed to even tell you the title of my first webinar and how my voice shook the whole way through!)
  • Launch an e-course (Check!)
  • Get interviewed on MarieTV (definitely still unchecked on the list, but everything’s a work in progress, right?!)

So what would be on your CEO Dare list? Aim to have at least 12 things on your list once you’re through with this step.

Get this template and more when you sign up for the CEO Dare Sprint here

If you’ve been at this business thing awhile (or dreamt about it for a long while) – another way to come up with dares is to reflect back on all your half-baked ideas and goals throughout the years that never came to fruition (Me right now: Oh hello, app idea circa 2017).

Step 2: Prioritize the Goosebumps

Once you have your list, you might be overwhelmed by sheer daringness of the whole thing. These things are going to take a lot of guts, determination, and faith to really go for.

Luckily, our job isn’t to tackle all of them at the same time. That’s a recipe for failure.

But go through each item on your list and put a star beside the ones that make you the most nervous. From the items that remain (the un-starred ones), go through and pick one from those to start with. We’ll be working our way up once you’ve done a little Daring-CEO muscle training!

Once you’re done with this step, your goal is to have your next CEO Dare chosen.

Step 3: Get Accountable

Want to know the best way (for most people) to follow through on something?

Tell the world you’re going to do it.

So that’s exactly what to do next. Just kidding.

But you should tell someone. Pick someone who you look up to and wouldn’t want to let down – a mentor, a biz BFF, a Facebook group full of your favourite people.

Tell them what you’re planning on doing (your next dare) and by when.

Step 4: Create a Next Actions Map (and ditch the to-do list)

To-do list? I think you mean to-don’t list.

Seriously, as much as I love a good to-do list, I think in the case of the CEO Dares they can do more harm than good.

I mean if I were to tell you to sit down and make a comprehensive list of all the things you needed to do to successfully complete your chosen dare, you’d likely feel so overwhelmed making or seeing the list (even if just subconsciously), you’d be on the first train out to quit-town.

What I love doing for the CEO Dares is to create a next-actions map.

Here’s what to do:

  1. Identify what you think are the projects within the dare (think bigger milestones)
  2. For the first milestone, brainstorm the next 3 tiny actions (25 minutes or less) you’ll have to take next
  3. Then when you’re finished with those 3 action items, re-evaluate the milestones and brainstorm your next 3 actions

Simple, right? Doing it this way allows you to focus on just the most crucial next steps instead of getting distracted/overwhelmed/future-spiralling over everything that’s to come.

Plus you’re going to be learning so much through the process of taking action, that you’ll be better able to adjust your plans as needed!

Step 5: Take Your First Action Now

There’s only so much planning we can do before we’re required to take action.

And since the hardest part is starting, get that out of the way by knocking out that first sub-25-minute task out of the way.

That first step will be the catalyst you need to keep taking action and see this thing through!

Step 6: Do or Schedule the Next Two Action Steps

For the two action steps remaining, take the time to complete them now or add them to your calendar at a specific date and time to complete them.

“If it’s not scheduled, it’s not real.” – Marie Forleo 

You’ll complete these before going back and brainstorming the next three actions, where you’re at in relation to completing the goal and evaluating the milestones you laid out in step four.

Step 7: Celebrate and Nurture Yourself with Self-Care

Taking action this way is going to require a little nurturing. So treat yourself to something a little fancier than you’d typically enjoy. How you celebrate is entirely unique for you.

Maybe that’s a massage or a new book. Maybe it’s a night of tea and reading. Maybe it’s a day off.

Pick something though to celebrate yourself for taking action (because, you, my friend, are in the minority and deserve to be celebrated!)

Step 8: Redefine Success and Failure (detachment and attachment)

We are focused on building the habit of being a Daring CEO. Of taking consistent action towards something that maybe has us a bit nervous or unsure.

So to do this consistently, we want to shift our perception on success and failure to be about the action, not the outcome.

When you take action = you’ve succeeded even if you don’t get a yes or the outcome you were wanting.

I like to think of it as becoming ridiculously obsessed with action and detached from what comes of it.

When it comes to my business, it’s all one giant experiment, and if something doesn’t go my way, it’s just data for when I try again next and not some personal judgement on my business or me as an owner.

Step 9: Make it a Regular Thing

Another component of making this habit stick is making it a regular thing. This might mean that you’re choosing and tackling a dare on a monthly or even weekly basis.

But seriously, can you even imagine what your business would look like after a year of these dares?

The connections you’d form? The opportunities you’d have created? The people you’d reach and help?

Step 10: Reflect Regularly (see the ripples)

Without regular reflection, it’s difficult to appreciate the progress and results you’ve been having. So reflection is a big part of the Daring CEO habit.

  • What dares worked? Which didn’t?
  • How consistent were you with taking action? Any patterns?
  • What opportunities came to you as a result of your CEO dares?
  • Any new ideas for CEO Dares you feel called towards?

In my own business, I do both a weekly reflection and a monthly one that’s a little bit more in depth. I have Typeform questionnaires with these questions that email me my forms and add them to a Trello board so I can easily go back and review them as needed.

Take Action

If you want company and accountability in your CEO Dare journey – you have an open invitation to my CEO Dare Roadmap – a FREE 5-Day Email Course guiding you through choosing, planning and tackling your first CEO Dare. Just click here to sign up!

Download the CEO Dare Roadmap by #DaringCEO