New Project: Three Months of Free Mentoring


This post is directed at those of you who replied “yes!” to a question I posed on social media earlier this week. Thank you for your incredible feedback! You are the reason this project will come to life.

Over the years, I’ve learned how powerful it is to have a mentor – someone who I respect, who has a wealth of knowledge and experience on topics that interest me, and who is supportive and giving of their time. My parents are my mentors. All my bosses have been, to some degree, but my current boss is certainly a mentor to me. And Gail has become an incredible mentor and friend. I am truly blessed.

I’ve never asked anyone to be my mentor before (and some of them might not even realize that’s how I see them!). Instead, I think our friendships/relationships just sort of morphed into that. Each time I talk to any of mine, I ask a million questions and am always writing things down. They share their experiences, and usually suggest books/websites/other resources for me to check out, and I always walk away from the conversations feeling inspired to tackle something new. (The best feeling is following up and telling them when I’ve accomplished a goal!)

As I mentioned a couple weeks ago, I’ve had what seems like a dozen new project ideas pop into my head lately – especially while I was travelling so much. I’m always going to write, but I keep feeling like I want to do something more. Sarah recently told me that if I had a “superpower” it would be making and building connections with people, and that really resonated with me. I do love talking to people one-on-one and in groups (like our meet-ups this summer?), and I love the little community we’ve all built on this site together. But how can I take it one step further?

Mentoring others was the first thing that came to mind. I get emails from some of you, and check-in from time-to-time to see how you’re all doing, but I’d love to do it in more formal setting. In the past year alone, I’ve had at least 8-10 people ask if I’d work with them/family member/friend, and I sort of shrugged it off because I didn’t know what that would look like – but now I do. So, I finally took this question to Facebook and Twitter on Monday: If I offered 3 months of free mentoring (emails, calls, Skype, etc.) would you or anyone you know sign-up?

Your responses were so unbelievably positive! As a result, here’s what I’m offering:

  • Three months of free mentoring to 5 people from December 1st – March 1st
  • 1 x 30-minute introductory call in December
  • 1 x 90-minute call in December
  • Your choice: 1 x 90-min call or 2 x 60-min calls in January
  • Your choice: 1 x 90-min call or 2 x 60-min calls in February
  • Email response time: 48 hours

If you were serious about your “yes”, or if you’re just reading about this for the first time and are interested, please fill out this short survey! As you’re doing so, remember that we can talk about anything: debt repayment, your career, minimalism, healthy living, other goals… whatever you want!

Based on the responses, I’ll choose 5 people I think will be a good fit, and will let everyone who responds know either way via email on November 17th. If you’re chosen, you should expect a little bit of homework from me before our first call. It won’t be too tough, but I really want to make sure you get something out of this experience. I also can’t imagine a better time to start this project: we can lock down some goals in December, then start to tackle them in the new year!

Now I’m curious: have you ever had a mentor? (Or even considered someone to be a mentor, even if you didn’t actually call them that?) What did you enjoy most about talking to/working with them?

  • I have two professional mentors in my field of work for several years now. They are both very successful women who have proven so valuable to me and have helped me immensely with advice and direction.

  • What an awesome thing to do Cait, and for free! I have had several mentors over the years that like you, probably didn’t even know they were. Right now I have one close friend who is kind of my voice of reason who I always bounce ideas off of. It’s nice to have. Let me know you want me to shoot you over any old life coaching materials I still have around.

  • This is so awesome of you to do. I’m definitely interested. As for mentors – my PhD supervisor was a huge mentor to me. Not just in that she was my boss for many years, but in areas that weren’t always discussed so openly (like being a woman in the physical sciences, and how it’s better but still not great), how I needed to present myself with more polish, etc. She was amazing to me. And now it’s morphed into a friendship situation rather than “you’re my supervisor and I’m your student.

  • I have no doubt you are beginning a phase of your work life that will morph over time but mentoring will be with you as long as you live. The rewards of mentoring others are more than you can possible imagine, you will receive more than you give and your work will inspire others in ways that reshape our way forward.

    Congrats. No money at all can reward more than mentoring.

  • My mentor is MY MOM! She’s one of the most level-headed people I know and never “fluffs” her advice, meaning she says it like it is. She is even my go-to for boy advice haha. Seriously, this woman has taught me everything.

  • Superb idea and I’m sure a lot of people will have to benefit from something like this. I’d sign up myself, but my time now is horribly limited with the baby, so I’ll probably have to leave this for sometime in the future.

  • I have had 2 amazing work mentors. One who is still in my life. I have never had a personal mentor before. I mentor people through work as well.

  • What a great idea! I’ve had (and have) mentors at my job, but I’ve never had a “life” mentor other than my parents and husband (we mentor each other :) ). It’ll be interesting to hear the results of this project–I hope you’ll keep us posted.

  • Love this idea! Way to give back :)

    I’ve had a few people I would consider mentors in my field of journalism. Much like you seem to have in your life, they don’t start out with me viewing them that way, but it evolves into that relationship.

    I think the most important thing about my relationship with my mentors is having them as a (expert) sounding board for when I have career dilemmas. It always helps to talk to some you trust who is more experienced in the field.

  • Excited for you and this project! I think it’s going to “birth” some awesome stuff for you and your mentees. Wait, is this the big project or is this a small side project?

  • Oh I forgot to mention, I’ve had one really awesome mentor who was a local politician. Because we attended meetings together, he would end up giving me advice about the way all of this city politics and business stuff works. I feel like we had the same philosophy of working smart and not hard for no reason, so I learned a lot from him.

  • Hi Cait,
    I just found your blog and am working my way through the archives from present backwards. Your mentoring program sounds like an amazing idea. How did it work out? Are you interested in doing it again? I’m in a career (medicine) that has had every step dictated, and now I’m looking to branch out and switch careers but have no idea where and how to start. I would love to hear more about your journey to freelancing.

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