Designing The Life You Want

I changed almost everything about my life two and a half years ago.

I had a full-time job as a teacher in a magical school (a job I had been working towards for years) and I was finally there. I kept reminding myself, “You made it! You did it!” but there was this voice in the back of my head that kept asking, “But what if…?”

“What if WHAT?!” I would respond in frustration.

Because part of me knew that something didn’t feel totally right, but I didn’t want that to be true.


I reasoned with myself. “Well all jobs have their challenges,” and “Maybe you just need to switch to another grade, or have more ownership over the program.” Because it’s no lie that I genuinely love teaching and if you’ve seen me with kids, you know I can’t fake that kind of enthusiasm, but it’s also true that I was extremely jealous of Greg and his artist/self-employed lifestyle. And if I’ve learned anything, it’s that jealousy can be our most powerful teacher and guide.

I resented my alarm clock with a fiery passion. I hated getting 6 pages into my book only to have to go sit in traffic. I didn’t like having to pack my lunch every day, or that the use of my time was primarily dictated by others. I felt like my brain and heart were only being partially used and I couldn’t help wondering if it was possible to find or create work that would make better “use” of me. (Plus, I was spending my free time writing this blog, learning about organization and time management, helping friends declutter, and creating and selling Planners… as they say, it’s always easier to connect the dots backwards.)

I was also reading books on “life design” (i.e. 4-Hour Workweek) and listening to a heck of a lot of Tony Robbins (i.e. Personal Power II). Eventually, the fear of not going for it was greater than the fear of just trying, so I took the leap.


I learned that…

  • It’s scary to open up to the idea of changing your life (our ego tends to be defensive when we start asking ourself if anything could be improved upon)
  • Creating change is way more possible than it seems, but you need extreme clarity (what exactly do I want, and WHY do I want it) and getting clear on those specifics is the real work
  • Many of the barriers we believe to be unmovable facts of our lives have to do with our perception. As my grandmother says, “Don’t look for a path without obstacles –  just decide, am I willing to tackle these challenges or not?”

I’m certainly no expert and I’m learning more about this stuff every day, but in case you have a little voice that asks you “What if?“, or if you feel jealous of someone else’s life, I wanted to share the three key steps that have been helpful to me (as guided by the books and audio tapes mentioned above, which I highly recommend!).

The benefits I’ve experienced in the past few years have been HUGE. Not only have they made me a happier, more relaxed and more fulfilled person, but they’ve made it possible for us to move back to PEI – something I previously thought was impossible.

It has also been enormously challenging and scary (so much uncertainty, hustle, grit and grind, the need to believe in myself more than I ever have before, and to generate all my own ‘wind’ to move my ‘sailboat’ along). I’ve needed to trust myself A LOT more than is comfortable, and I’ve felt crushing self-doubt in the face of real setbacks and failures (especially in wanting to secure things financially for our new baby). Not only that, but people rarely understand what I do and seem to think I’m more “in-between” jobs than “in” a job. They also sometimes assume Greg is bank-rolling me, or figure I had some kind of breakdown. Plus, I do still hear a little tape in the back of my head that says ‘If you aren’t working all the time, you are being lazy,’ but I’m getting better and better at turning down the volume. I am internally so much happier that it’s hard to give that many figs about how people respond (but it’s also hard to give “no” figs).


So without further ado, here are the three steps I took to revamp my life:

STEP 1: I Answered This Question

 If you had $100 million in the bank, what would your days look like?

I said:

  • Wake with no alarm
  • Read!
  • Daily exercise (flexibility in terms of when/where I go)
  • Make good food with room for spontaneity (more time to cook earlier in the day)
  • Feel helpful and useful to others (through work and other activities)
  • Spend lots of time with people I love
  • Do things that challenge me and help me learn/grow every day

STEP 2: I Figured Out The Moolah

I got meticulous in understanding the cost of our life (all current expenses, spending habits, savings/retirement goals, etc.) and also what extra costs would exist in our “ideal” life. I wanted to know “How much do I actually need to earn to live the way I want to live?” vs. coming up with an arbitrary salary under the assumption “more” is better.  The benchmark I used initially was to maintain my full-time teaching salary, because I felt like we had more than what we needed with that income.

Obviously it’s necessary to re-examine financial targets every year as circumstances change. This past year, we had to account for a big move to Canada (expensive!), buying a house, and everything that comes along with home-ownership (gulp! new boiler? new oil tank? new roof? taxes!). And now we need to consider our goals in terms of our growing family. The point is, having an intentional salary goal based on asking yourself what you want your life to look like is different than making your life fit into the salary you have.


STEP 3: I Got Crystal Clear On What I Wanted and Why I Wanted It

I wrote…

I want to be able to live anywhere. Greg and I love LA, but we also love Toronto and PEI… and we love traveling!  There are so many places we want to explore. He already has the flexibility to live/work anywhere, and I want the same kind of flexibility.  I also want to do self-directed work that feels meaningful and specific to my set of skills and passion, that challenges me and requires me to be creative on a daily basis. I want to start a family and be able to take a full-year maternity leave and then work from home in a flexible way so I can be home a lot during our kids’ early years (while growing a business, and contributing equally to Greg).


  • Work 10-12 hours/week
  • Earn equal to Greg
  • Work 8 months/year (4 months off)
  • Contain work to 3-4 days/week (and not during evenings/weekends)
  • Freedom to work from anywhere (virtual work)
  • Ability to take a year off comfortably for each baby and primarily be at home when babies are young


  • Helpful and useful to others
  • Challenged (really using my brain and skills)
  • Efficient (vs. feeling like I’m wasting time on useless tasks imposed by others)
  • Open and flexible in terms of how I spend my days

To get started, I quit my full-time job, and started offering private piano lessons (it was work I could do from home 12 hours/week, 36 weeks a year, while maintaining my teaching salary). Gradually, I built the coaching business up, shifting the balance from piano to coaching until I was running my business full-time.

I now meet my financial targets through a combination of:

  • 1:1 clients
  • Small group training programs/workshops
  • Speaking engagements
  • Products (e-courses)

Speaking engagements have been a great source of income for me, as well getting hired by companies to provide 1:1 or small-group trainings for their employees. I work with a maximum of 8 individual clients at a time (12 session packages). My students all work with me on the semester cycle (from September-December or January-April), but I’ve been more flexible with adults (i.e. working with them over the summer etc.). I hope to eventually keep all of my clients on the same “school-year” cycle and protect at least 2 weeks in December + 2 weeks in April + the entire summer as vacation time.



(*Black font = my original goals. Purple font = what is currently true.)

  • Work 10-12 hours/week *More often 15-20 hours/week 
  • Earn equal to Greg *Closer to 80% 
  • Work 8 months/year (4 months off) *Working 10 months/year (2 months off)
  • Contain work to 3-4 days/week (and not during evenings/weekends) *4 days/week
  • Freedom to work from anywhere (virtual work) *Yes
  • Ability to take a year off comfortably for each baby and be at home primarily when babies are young  *I’ve budgeted for a full-year maternity leave with this baby. My plan is to reassess after 8 months and decide if I want to stay on full maternity leave or resume with a partial coaching load. One of my main motivations in doing this was to see if it was possible to run a business while also being home as much as I want to be… time will tell.

*And ALL of the “feelings” targets have been met… which is the best part.

So I’m not exactly where I aspired to be, but I’m a LOT closer than I actually thought was possible when I dreamed up this list. The baby will be a total shake-up so I will reassess what I want our life to look like as I go.

I honestly can’t predict how I’ll feel a year from now (maybe I won’t even want to be self-employed anymore, who knows?!), but I like knowing I can redirect myself when I want to.

Feel free to reach out if you have any questions, and thanks for reading!

❤ Kailea

2 thoughts on “Designing The Life You Want

  1. So much light and love coming your way, Kailea, and so happy for the adventure and gift of your new family member arriving soon ❤️


  2. Great read! Wish I had found this a few years ago, it might have made my own life transition a little easier. I’m a fellow Loran scholar who has just abandoned a great career in the federal government and returned to school full time for 2 years (and I can’t underscore how much I was dreading the return to school) to become an elementary school teacher. My decision had zero to do with having summers off (despite what everyone assumes) and comes at a huge financial cost but I couldn’t keep wishfully wondering about the career I’ve always thought I wanted.


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