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Career & Money Experiment #2: Contact a CEO

Even if you have all the weapons for success in your twenty-something career (brains, talent, drive, etc.) you are bound to be lacking in one area of your professional arsenal: experience. The most efficient way to make up for that deficiency is by stepping out of your comfort zone and reaching out to the most experienced role model you know, a CEO! This experiment is the application of one of my Happiness Fundamentals: Seek out your gurus. By working alone in the pursuit of your career (or any other arena of your life, for that matter) you are putting a ceiling on your potential. You are going to have to start training yourself to take these kinds of risks if you want to get to the next level of your career, and quickly!

Reasons to Reach Out to a CEO

  1. These people have a proven track record for success. Whether your Career Guru is someone who inspires you personally or someone who simply created a business model that you want to replicate, the opportunity to learn from them is EXTREMELY valuable.

  2. As I mentioned above, you have NOTHING TO LOSE! Worst case, they don’t respond. Best case, they decide to take you on and mentor you. Most likely, you will receive a response from their assistant, thanking you for the e-mail and explaining that your guru is currently very busy.

  3. Even a one-sentence response from your Career Idol will do something magical. It will take them off of a pedestal. It will remind you that this wildly successful inspiration of yours is a human too. AND. Are you ready? You are just as worthy of great success as they are.

How To Properly Reach Out to a CEO

  1. Do your research. Find out the best way to reach the CEO and then set out on getting their e-mail, number or address. If they have a social media account try reaching out there! Some CEO’s have no direct contact, so you may have to try reaching out to their staff first.

  2. Be brief. Yes, you miss 100% of the shots you never take. So you should always take a chance and reach out! That being said, if you are able to procure their e-mail, remember that CEOs are very busy people and are much more likely to respond if they have one question to answer, rather than 10.

  3. Be heartfelt. You are reaching out to this person because they inspired you. Briefly explain how exactly they impacted your life. Not, “Oh my God, I love your work!” Well, duh! Instead, mention something specific like, “Your Tendencies Quiz helped me better understand that not everyone is a ‘Questioner’ like me. Since discovering this profound truth, I have become a better boss, friend and wife.” (← That is an excerpt from a real e-mail I wrote to Gretchen Rubin, Total #Girlboss & Author of The Happiness Project)

  4. Offer them something (if you can) before asking for something. What can you offer a CEO who seemingly has everything? Chances are, an invite to lunch will be more of a burden for them than a gift. As we already know, they are super busy and might not even take a lunch! Do your research and find out what they are currently working on. If you are contacting a CEO who has written a book, it can be as simple as mentioning that you plan on buying their book and gifting it to your friends and family for Christmas! Or if you have a blog like me, feature them. People never get sick of free promotion. 😉

  5. Ask a question or Give a Call to Action. Here is where you have the opportunity to gain something priceless. Ask the one, extremely insightful, mind-blowingly brilliant question that you’ve been dying to know! And don’t be afraid to sound enthusiastic. You’d be surprised at how contagious your enthusiasm can be. “I just have to ask, because since seeing your TED Talk, I have been dying to know…” Alternatively, if you have too many questions to ask, you could really go out on a limb and ask them for the pleasure of a brief (10 minute) phone interview. If they do say YES make sure you keep the call to the agreed time, but be prepared with at least 25 of the most thoughtful, witty questions you have ever mustered.

In case you were wondering, here is my experience! I reached out to:

  • Gretchen Rubin, Author NYT #1 Best Seller The Happiness Project, via e-mail and SHE RESPONDED!! Offering both advice and words of encouragement for writing.

  • Will Dean, CEO of Tough Mudder, via Facebook Message (No response. Even though it was such a witty message! Ha, you can’t win ‘em all)

  • Tara Milhem, Recipe Developer & Instagram Sensation (@TheWholeTara) Not only did she respond, but she was willing to have an interview and I was able to feature her as a Body Month Happiness Guru!

  • Dr. Meg Jay, Best-Selling Author of The Defining Decade. Her publicist responded explaining that Dr. Jay is busy researching for her next book.

  • Danny Dover, TED Talk Speaker & founder of We have now corresponded quite a bit and follow each others blogs/Instagram accounts! He has agreed to an interview and will be featured as a guru in Passion Projects Month.

This is such a fun experiment because it lets you dip your toes in the water where the big fish swim. I got such a rush every time I pressed send on an e-mail and can’t wait to see how it helps your confidence, changes your relationship with risk, and possibly even expands your network to include some CEOs! Go create your dream contact list and your experience in the comments below!

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