Professional Development

By the Time You Leave, Make Them Know Why You’re in the Room: and other takeaways from the mentors and keynotes at Create & Cultivate Chicago 2018 Conference

Successful, inspiring executives, entrepreneurs and creatives Ben Silbermann (Pinterest), Maxie McCoy, Blake von D, Shay Mitchell, Alli Webb (Drybar), and Jennifer Hudson all spoke at Create & Cultivate Chicago 2018.

Create & Cultivate conference was nearly a month ago in Chicago yet I’m constantly reminded of the awesome advice gleaned that day. In the weeks since the career development event I’ve been following up by listening to speakers’ podcasts, signing up for their newsletters and more, to make sure my skills and motivation are top-notch. Just as I recapped the panel sessions on my blog, here are the key takeaways from C&C’s keynote speakers and my mentor sessions.

Coffee & Conversation with Ben Silbermann, founder and CEO of Pinterest

  • It is better to have a product that a few people love than a product that a lot of people think it okay.
  • There’s not a right time to start a business.
  • Put together a great team. Find people that share your values but have different skill sets.
  • Invest in yourself, your health, your family and friends, and the support system around you.
  • People need to learn how to rest rather than to quit.

Mentor session with Maxie McCoy, writer and speaker

  • Feeling lost is a universal experience. Celebrate yourself and talk about the amazing things that you’re doing.
  • [When working on multiple side hustles] prioritize what makes you money and let your creativity take flight.
  • If you want to turn your experiences into speaking engagements, practice.  In small groups test your skill set and material, locally. Get practice and then create marketing material about what your talks will be.
  • Sincerity matters. Authenticity is over talked about.
you're not lost
Maxie and me! She signed my copy of her new book, You’re Not Lost.

Mentor Session with Blake von D, attorney and digital influencer

  • Plan your content. Take a Saturday and get done what you need to (you might need to skip brunch with your girls!).
  • Learning how to edit will boost any photo. Reach out to seniors in college looking to build a portfolio or have a shoot with other bloggers and do eight looks in one day.
  • Use the most of whatever audience size is yours.
  • Comparison is the thief of all joy.
  • Poor man’s trademark: Email a creation to yourself for the timestamp.

Keynote Conversation with Shay Mitchell, actress, model, entrepreneur and author

  • Focus on confidence outside of physical appearances.
  • Don’t let the world be a scary place; go out there and explore.

Keynote Conversation with Alli Webb, founder and chief creative officer at Drybar

  • Hire people who know the things you don’t, and before you need them.


Keynote Conversation with Jennifer Hudson, singer, actress, and spokesperson

  • Chicago is a real, real place.
  • If it’s not worth working hard for it’s not worth it at all.
  • Success is when you achieve what you want to do.
  • Your love for what you do will keep you going.
  • We don’t call it luck we call it blessings.
  • By the time you leave, make them know why you’re in the room.


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