The 20 Monday Project: Behind the Scenes on Why I am Leaving My Corporate Job

blog day in the life entrepreneur business coach side hustle into passion Dec 15, 2021
Holly Haynes sharing behind the scenes on leaving her corporate job to go fulltime in her business

In today's blog post, we are getting personal. I am sharing a personal update and FYI.


I put my notice into my corporate job last week.

Which means in almost two years I have grown enough to support our family full time with this business. And officially having 22 years in corporate, I have retired.


Just saying this kind of makes me want to throw up. I am not kidding I am probably covered in hives under my pj's as I write this. But, I know it is the right step for our family. And I have shared this whole journey with you through this blog so I thought it made sense to share this too. 


My last day will be the end of 2021 and will start the new year as a full-time entrepreneur. 


Let me backtrack a little bit and give you the story.

My goal (which I have shared) has always been to have a flexible schedule. Whatever that looks like. Ideally, I want to work 3 days a week. 


As the business grew this year, especially this summer when the mastermind sold out in a week and the planner got picked up in HomeGoods, I could see the goal in sight, but still wasn’t sure. So I gave myself a challenge. I always do this because it allows me to dial in my focus for a period of time. I called it the “20 Monday” project. As in give yourself 20 Mondays to put a plan together for corporate retirement. (At this time my “date” to leave was the end of March). 


It is funny when you put something out in the universe instead of just on paper. I shared it with my mastermind community and as a family, we worked towards the plan. 


We created a big whiteboard which you may have seen behind my desk on stories that said 20 Mondays and wrote down everything that had to be in place as a family. Everything from needing a new computer, to family benefits, retirement, insurance, etc. 


Then things got interesting from a back-to-work perspective. I always knew I had to go back to the office but certain policies about returning didn’t resonate with me. I also started getting debilitating migraines from being on so many zoom calls and just wasn’t in alignment with the work I was doing. All these signs were pointing me in another direction. So I listened. Which honestly I feel like is what you have to do as an entrepreneur. Listen to your gut. 20 Mondays turned into 4 which at the time this publishes will be 2. 

Do you love these tips? Take the Productivity Personality Quiz to get a Netflix-style binge-worthy resource list to help you find your focus and is customized to you! Take the quiz here. 

I 100% believe you can build a very full-time business on a very part-time schedule and I will continue to do that and share that. I am passionate about teaching you the steps I took so this can be your journey too.

The trick of this whole equation is that I don’t want to work more.

I want to work less.

I want to go to yoga on Monday mornings at 11 (I still can’t even imagine this btw), I want to host retreats (more of them) without having to take off work, and more importantly, we love to travel as a family. One of our BIG goals is to go abroad for several months at a time. There are also new products I want to create (hello a line at Target, that is on the vision board) and the Crush the Rush membership, which is just getting started and already so powerful. So this is the first step in making all this happen. 


We also have a team now. Kaitlyn, who I hired last December to help with re-purposing content (which p.s. is one of my #1 tips to scale faster) is now managing our entire community and is our Director of Community Operations. 


My husband Scott is our Director of Operations and Finance. Think taxes, accounting, and all things planner logistics. We spent HOURS last week planning next year's planners which I can’t wait to share. 


I also have a few partners I work REALLY closely with. The Ybanez Media agency and their founder Kayla, helped me build out all my back-end funnels (i.e. we turned all the old ones off and create new ones with a brand new freebie coming soon) leading up to this. And Taylor at Taylor Anne Creative. She moved our entire planner site to Shopify, helped me with Kajabi integration, and is the creative brain behind our new gifs, and even more exciting the new 2022 planner covers. 


This was all in the 20 Monday plan.

Set a foundation. Build a community. Have trusted partners. (I kind of want to write a book about this now, but one step at a time!)


It's been a crazy ride these last few weeks thinking about new insurance, business liability coverage, additional legal coverage, and all the things that you won’t see in the “oh I quit my job" post. It has not been glamorous to get to this point. And if I am being really honest there have been tears. And nerves. And Anxiety. Will this work? Can my husband and I really work together in the same house?? (we have been for a few months, so it was an educated guess that it will), but my point is, there is A LOT of thought that has gone into this. 


I also want to continue teaching how this happened. Building multiple income streams while working full-time, hiring a team while still working, and basically making very planned financial decisions to set us up for this. Everything was built with intention. 


So there you have it. What a way to end 2021, right? I hope this blog post inspires you (because 6 months ago I really didn’t think I would be sharing this) and if anything, know that I want to share everything as I go through it so you can build your dream schedule as well. 


If you listened to this and it resonated with you, shoot me a DM. Sometimes putting your life out in the public spotlight is scary, but I thought this message and story was way too important not to share. 


Looking for more on this topic? Check out the Strategy Lab in the Crush the Rush Club! 


Are you bursting with ideas and wondering how the heck you are going to find time to make it happen?

Imagine your time management fairy god-mother coming in to wave her magic wand and show you a better way! And actually, see results. we combine productivity best practices, business strategy, and community support to help you get to the next level without burnout.


Holly Marie Haynes is a business strategy coach, podcaster, mom of twins, and founder of the Crush the Rush brand. She helps women create simple scaleable offers and systems to grow to multiple 6-figures.

Holly Marie Haynes is a business strategy coach, podcaster, mom of twins, and founder of the Crush the Rush brand. She helps women create simple scaleable offers and systems to grow to multiple 6-figures.

© 2022 Holly Marie Haynes, LLC |