10 Steps to Creating an Exit Strategy That Feels Good

May 18, 2021
10 Steps to Creating an Exit Strategy That Feels Good

I was interviewing a friend of mine in our UpLeveled Educator community last week (come hang out with us!) and something he shared really got me thinking.

How do you know when it's your time to go? 

And then that question had me thinking even more…

And then what do you do about it?

Like me, Erik is an educator turned entrepreneur - he went from being a speech and debate coach and teacher to braving the unknown and stepping into entrepreneurship as a speaker and coach. 

I asked him how he made the transition from education to entrepreneurship and he shared a beautiful story that was similar to my own. For Erik, it was about recognizing when he wasn’t actually serving his students any more; the fire was gone and by sticking around he was actually doing his students a huge disservice by prolonging the inevitable departure.

For me, I remember clearly the exact moment when I realized it was time to go. My little one was “graduating” from kindergarten and we were having a big family potluck and celebration. All the parents were gathered around, crammed along the walls of the teacher’s classroom and all the little ones were swarmed around the teacher on the floor. She was sitting in a chair and it was like those kiddos couldn’t get close enough to her. She had curated end-of-year awards for each child and as she passed them out, she told short stories about why this child was receiving this award.

At one point, she looked up at all of us parents and said, through a cracked voice and tears in her eyes:

“You know, this isn’t just a job for me. This is my life. This is my passion. And I love each and every one of your children very dearly.”

All the parents were crying and through my own blurred vision, I had the epiphany. 

I no longer felt that way. And my students deserved an educator who did.

Yes, I most definitely shared that love for my students the way she did. Man, I would do anything for those kids - and I did - but that was where my love and passion for teaching had stopped. 

That was when I knew it was time to start creating my exit strategy. 

Are you connecting with any of this? Have you had this moment too? So, maybe it’s time - just like it was for both me and Erik - to start thinking this through. And maybe sharing my exit strategy might support you in creating yours. This is what I did to successfully transition, without burning out or burning bridges.

Here’s 10 steps to creating an exit strategy that feels good:

  1. Use your classroom/campus as a lab - experiment, play, discover, dream, test hypotheses and eliminate ideas that don't fully align with your vision and next steps.
  1. Talk to as many people as possible about opportunities beyond the classroom (without telling them what you’re up too! Remember you are just in the experimentation phase & you don’t wanna burn bridges by revealing too much too soon.)
  1. Talk to yourself on a daily basis with questions like: “How do I want to feel? What kind of impact do I want to make? Who do I feel called to serve? What kind of lifestyle do I want to live?”
  1. Say YES to every opportunity that might potentially open a door for you, provide you with relevant experience, create a pathway or solid vision of what is next for you. This also means saying NO to things that aren’t supporting your vision and next steps. Stay focused on the end goal.
  1. Talk to family and friends who’s opinions and values you trust and admire about your potential plans.
  1. Build, expand and nurture your network (you know what they say: your net worth is a reflection of your network!)
  1. Get intimate with your finances to determine your comfort level with your next moves.
  1. Draft a bucket list of things you want to come to completion with before you leave. Then commit to it and stick to it until you’ve completed it all.
  1. Based on all of the above, decide on an exit date and reverse engineer your plans so you can create the best possible outcome for everyone involved, starting with YOU.
  1. Get support to help you bring your vision to life; find a mentor, coach, program or assistant that you trust to collaborate, co-create and guide you through this transition!

Try this out, stick to the plan, and let me know how it goes!

And if you are really ready to start discovering what’s next, then come to our FREE Educators to Entrepreneurs Summit happening on May 27th & 29th. This is a summit for educators by educators from around the world who’ve become successful entrepreneurs and non-profit leaders. They will be sharing their journeys, strategies and habits to help you:

  • discover what's possible beyond the classroom
  • brand yourself as an impact-driven edupreneur
  • master your mindset
  • monetizing your mission
  • own your transferable skills
  • understand how entrepreneurs think differently

We’ll have lots of fun, dance a little and learn a ton. Oh, and there’s great freebies and giveaways too! More details here. See you there!


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