Erin Whitehead Feature

Headshot of CEO Erin Whitehead

Erin Whitehead, MBA is the Host of the AMBITIOUS AF Podcast where she spits fire and brimstone about what it takes to chase your most ambitious desires and become an uncommon force for good in the world. What sets the AMBITIOUS AF podcast apart isn’t just the operational tactics and strategies you can implement immediately or the top #100 rank internationally, but that Erin doesn’t accept sponsorships. All the podcast growth is organic and comes directly from word of mouth.

Erin is also a human performance coach and CEO of Kick The Ceiling, a concierge coaching firm committed to helping clients focus on results achieved through evidenced-based neuroscience. Her clientele includes ultra-high net worth individuals, surgeons, political candidates, professional performance athletes, and United States Special Forces and Veterans.

She speaks to audiences globally about how to consistently push past your next highest level regardless of circumstances. Erin is best known for publishing throat punch motivation on her social media channels that punishes the victim mentality and encourages personal excellence through grit, determination, perseverance, and radical endurance.

[Q U I C K   N O T E S]

Erin, can you start off by telling us about yourself and why you went into entrepreneurship?

Erin Whitehead in business suit sitting forward and smilingI’m Erin Whitehead. This is the section where I tell you who I am as an entrepreneur and why you should keep reading. Let’s start with my early career path, because that’s relevant. Here’s the most important thing you need to know about me when I was in my early 20’s…

I was fired from every job I ever held. And when I say “fired,” I don’t mean I was politely given a heads up about my last day. I don’t mean that it was a mutual decision over a gentleman’s handshake. I mean my positions were magically eliminated after my lunch break. I was told over the holidays to never come back. I was given legal defamation paperwork to sign in exchange for my last paycheck. (Yes, employers do that shit. Stop being naïve and wake up to reality.)

Since I had a poor track record of fitting inside the corporate mold, you’d think I would have become determined and motivated to be a better employee and keep a steady paycheck. But I was clueless and had no direction in life.

I will say this about myself: I always had bigger-than-life dreams. I just didn’t know how to achieve them. In fact, I didn’t even understand how to define success properly much less entrepreneurship. Like most people, I thought being your own boss came from being lucky, or having wealthy parents, or some sort of magical skill set that I was not randomly selected for.

Most people I came across in their mid-twenties seemed to have some sort of career path they were on… some ladder they were climbing… something bigger they were constantly in pursuit of. And every adult I had ever spoken with was pursuing their own version of success that somehow placed significant distance between them and all the losers.

But not me. This was a concept I couldn’t grasp. And, I really couldn’t get myself to care about finding the perfect corporate career nor keep my mouth shut long enough after I got hired to make it past the probationary period of employment.

The reality is, I didn’t care enough… because if I did, I would have had to admit that I was failing badly in life. Asking for help was too embarrassing. I damn sure didn’t have any money to pay for some sort of success program. And from the blatant irritation I constantly caused my bosses I figured I was too stupid to do great things in life. Or incompetent. Most of the time I felt like I was both.

Things didn’t really change much after that. I continued on as a low level worker bee, flew under the radar with whoever my boss was, and tried hard not to get fired. But I was still feeling torn between working for someone else and secretly wanting to chase my bigger-than-life dreams – with one exception.

A few years ago, my personal life took an unexpected turn and as usual things were only getting worse. Once again, I was faced with another “this isn’t working out” conversation at work. In that moment I knew I had two choices. I could beg and plead to keep my job or I could leave quietly and finally handle my shit once and for all. I decided to accept the termination. I was numb. I remember actually thinking, “those a-holes don’t even know the talent they just lost out on,” and also, at the exact same moment, feeling like a total loser who wouldn’t amount to anything.

You see… people today know me as a woman who is self-confident, assured, and disciplined who also happens to be the mindset coach to all the badass people I wanted to be like.

But I was naïve back then. And I didn’t know how to help myself. Just when I felt a little momentum in life, everything would get screwed up. Those moments caused a shit ton of self-doubt. And I became unenthusiastic about my future.

So, if that’s something you’ve experienced in your life, just know… I get you.

If you feel like you’re spinning in circles right now because you don’t have all the answers, then you and I have a lot in common. Seriously. I wasn’t born with superhuman capabilities or superior intelligence. In fact, it takes me longer than most to learn something new.

So, if you’re someone who has a dream to do something bigger with your life and you think you’re plain, or average, or ordinary…

Maybe you’re not the smartest guy in the room, maybe you’re not the strongest person in the world…

But you want to do something different with your life. You want to do something great with your life…

Maybe I can be an example of what’s possible as an entrepreneur when you chase your most ambitious desires, keep going, and never f*cking stop.

Erin Whitehead in teal shirt and smilingCan you tell us what drives you to be successful as an entrepreneur?

On weekends, government holidays, or vacations most people choose to look for a reason to not put in the work. They take the day off. They put their feet up. They take a “breather.” Most importantly, they put their goals on hold.

Achieving goals leads to success. Especially when those goals are difficult. That’s how I know that when life presents you with a difficult choice or an easy choice… ALWAYS choose the difficult choice.

When I look back on my life and the multiple times that choices were presented to me, every time I chose the easy path… I got f*cked. Every time I chose the path with more resistance and difficulty, I was rewarded. Not sometimes… always.

If you are whining about the state of your life today and you are unwilling to put in the work… you aren’t doing your f*cking part. Too many people are willing to rant, bitch, complain, point fingers, and scream into the phone. Not enough are willing to DO THE WORK.

Don’t like your job? Don’t like your living arrangements? Don’t like your financial situation? Eliminate the idea of “whose fault it is.” Instead, extend the amount of energy you place into chasing difficult goals. Including weekends, holidays, and vacations. And do the work that makes you feel like an outsider in your own skin.

Because this is your only life. And it’s ending one minute at a time.

Tell us about your current role and your vision of helping people become better versions of themselves.

I have never believed more than ever, right now, in our opportunity to dust off our courage and find our fire to become an uncommon force for good in the world. In order to do this as a coach, I take a real and raw approach. The kind of real and raw that’s contrary to public opinion. The kind of real and raw that exposes weaknesses. Because that’s how my clients fix the cracks in their own foundation. And that’s how they can become the type that breaks the cycle. That’s how shit changes. That’s how everything changes. And, that’s how they win!

I strongly suggest, if you want to eliminate excess stress and drama from your life you need to learn to be real and raw with others. Too many people beat around the bush for the sake of being polite. Just know, there is a beauty in telling someone the hard truth. Many people consider this approach rude or arrogant. But I believe… so long as what you’re saying comes from a place of truth and love, you’ll likely be shining a light on something that will help them. And, you’ll be saving your own sanity in the process.

Start being more direct and truthful. At the end of the day, people will actually thank you.

What’s the one or two accomplishments that you’re proud of?

black and white photo of Erin Whitehead on her podcastGreat question! Here’s what comes to mind when I think about accomplishments… Have you ever scrolled through your social media feed and noticed a “guru” trying to sell their lifestyle program that gets you to retirement by the age of thirty? If you just rolled your eyes thinking about how ridiculous it is, I’m am too. If these “gurus” really understood what embodies a true entrepreneur… someone who has winning in their blood… they would understand that true entrepreneurs DO IT FOR LIFE!

Most people equate entrepreneurship with exotic vacations and a fancy watch collection. Other people think that being your own boss means constant parties on the lake once they’ve “made it.”

True entrepreneurs wake up with the same intensity whether they can barely make rent or they command an empire. The harder the days are, the harder an entrepreneur fights. Because there is no end in sight. There is no plan to retire.

They love the thrill of the chase. They love the trenches of entrepreneurial warfare. And, most of all, they love to solve problems and make a positive impact on the world.

So, you have to ask yourself: which group do you want to be associated with? Do you want to spend your hard-earned money on some lifestyle program trying to retire early? Or, do you want to work your ass off today and tomorrow and the next day and every other day after that with no end in sight to build the life you truly deserve?

I know which group I’m a part of and if you’re truly an entrepreneur with winning in your blood… you’re in it for life, too!

What advice do you have for other up-and-coming business owners and leaders?

So many people come up with really great ideas in their mind. They want to start their own business. They want to change the world. And then the imposter voice in their head starts saying, “are you smart enough,” “what if it doesn’t work out,” “am I good enough?” So, they focus on their fears and self-doubt, slink back into their own mediocrity, and end up accomplishing nothing in life.

Here’s the hard truth… if you let your imposter voice tell you what to do, you’ll never make it in business or in life. You need to either be all in or be all out. Why? Because your imposter voice gives you the option to fail as an entrepreneur. It gives you the option to never change the world. Is that what you truly want?

Regret is one of the most painful feelings in the world. Especially when most of the time you have no one else to blame but yourself. And whether you like to admit this or not, you will die eventually. All of us will. It’s unavoidable.

So, here’s a question for you: would you rather lay on your deathbed thinking about everything you wish you would’ve tried but didn’t…

Or… will you look death eyeball to eyeball with a huge grin knowing you invested everything you had in pooling all your courage to take the first step, kept going, and never stopped building the life you truly deserve? So, what’s it gonna be?

Are you active on social media professionally?  If so, what platforms work best for engaging your followers?

Oh, hell yes! I show up on social media every day with the purpose to help people feel valued in a world that places everything and everyone else first. We’re all fighting uphill battles no one knows about. And I love reminding people that it’s normal to have fears, doubts, worries, and struggles just like the next person. And just because you feel like quitting doesn’t mean you don’t have what it takes to “make it.” It’s normal to want to quit. Just don’t. EVER!

photo of Erin Whitehead's personalized coffee mug on her deskWho was your biggest influence?

For me, it’s not “who” is your biggest influencer but “what” is your biggest influence. The perspective of time is the biggest influence of my day. For example, I see so many people picking up a success program or starting a new business, trying it out for a few weeks or a month, and then quitting on themselves because they didn’t become a millionaire overnight.

What they don’t realize is that someone else (with harder circumstances) entered that same success program or started the exact same business and worked harder and longer for more than a decade and made millions.

What does this mean for you? You have to give it time. You have to continue showing up with discipline and effort each day. If you only stick to things for a week, not much is going to happen. But if you stick with something for a decade… you’ll not only learn from your mistakes but witness your own tremendous progress which leads to success. And THIS type of success becomes part of who you are.

Invest in your long-term plan, give it time to materialize properly, and eventually you’ll be living the life you always dreamed of if you keep going and never stop.

What is the most challenging part of your work as a CEO?

Challenging the voice in my head that tells me, “You worked so hard yesterday, you deserve to relax today.” Having the discipline to persevere in spite of the beast in my head that’s reinforcing our natural tendency to be lazy is one of the hardest parts of my day.

Over time, I’ve trained myself to recognize the beast and shut it down immediately. This win supersedes any material goal I could ever accomplish… any house I could own… any amount of money I could have. And that means I can spend more time building tenacity and grit and all the other skills that encompass mental toughness. Because this lays the foundation for everything else I want to achieve in my life. And when you figure out this tactic and implement it, you realize… you CANNOT be stopped!

Erin Whitehead in pink shirt and smilingWhat do you have your sights set on next?

Reaching and helping more people. It’s a calling for me. But there’s another layer to this… people always remember when you help them in their time of need. And I know from experience what it feels like to be defeated and turn your back on the world. I remember the dark times in my life when I was down on myself. And I remember that special someone who stepped in and gave me the support to make through one more day.

Everyone goes through difficult shit. People remember those that help shine the light on what’s necessary and good in your life. You can be that person. Most of the time people just need someone to listen, to encourage them, to share wisdom and experiences, or someone to just be there. No matter how young or old you are you can always help someone in need. And that kind of helping hand will always come back to you when you need it the most. Never forget that.

What is a day in your life like?

Chaos, happiness, momentum, discipline, grit, and everything in between. I wouldn’t trade it for the world.

Do you have any hobbies?

When I’m constantly in pursuit of my highest potential and chasing my most ambitious desires every single day, I don’t forget to lose sight of what makes me feel fulfilled. I take a few moments to recognize the things that bring me joy. I appreciate the lifestyle I currently live. I cherish my time with those I love the most. This gives me the enthusiasm and energy to keep chasing after more.

What makes you smile?

Gratitude is one of the greatest accelerators of success. I’m not talking about the “#gratitude” posts that are sponsored and chase your double taps. But the real, genuine gratitude from waking up and feeling amazing from your soul. So, I often pause in the morning for a moment and smile… because I know life is really good.

What are you never without?Erin Whitehead in white dress and flowers in her hair

People talk all the time about building confidence before you try new things. I say bullshit. You can’t win in life without courage. If you lack courage, it’s literally impossible to win. Period. Go take action. F*ck some shit up. Learn from all of it. And, keep going. That’s what you should never be without. Courage.

What scares you?

I love the feeling of trying something new in my business and being scared shitless. It means I’m probably on the right track. Facing these fears keeps me in a growth phase. And that’s when I can learn something new. (It’s when I stop feeling scared, I start to worry.)

Other work, published articles, interviews or accomplishments:

Podcast on Coruzant

~ Erin


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