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Upgrade Your Life + Business in Just 1 Hour A week


Upgrade your life + business in just 1 hour a week! Join a dynamic and engaging community of women who value their TIME above all else. With 2 monthly LIVE! calls with Cailen plus action plans and community support, you'll learn how to work less, make more and live better right now.


Do you ever wish you had...



  • A clear, step-by-step plan to build and grow your business
  • On-going support and guidance from someone who knows what works and what doesn't
  • High-touch accountability to ensure that you will not fail
  • Proven techniques, tools and strategies to create lasting success on YOUR TERMS
  • The ability to focus on the action items that are best for you, your life and your business (and kiss shiny objects and overwhelm goodbye!)
  • Systems for making money, improving your mindset, growing your business, expanding your community, selling your offers and finding ideal clients that WORK and feel good!
  • Unwavering confidence that comes from knowing that what you're doing will work!

...then it's time for Design Your Life School ™


My Story...

Hi there! I'm Cailen Ascher, a Lifestyle Design Expert and creator of Design Your Life School™.

Through all of my programs, products and coaching, I help women bring intentional design into their lives and businesses so that they can stop living by default and start creating success on their terms.

The moment intentional design clearly moved to the forefront of my life was after the birth of my first daughter when I shifted to a 3-day workweek.

After that decision, everything changed for me. I went from feeling like a failure in business (and life) and making practically no money (seriously, I made just $22.50 in July of 2015) to having a $30K launch in February 2016 and crossing the 6-figure mark in my business just 8 months later! Then, in 2017 I used the principles of intentional design to take 4 months off after the birth of my 2nd daughter and still increase my income by 15%.

The intentional design of my life and business changed everything for me. My business got better. My life got better. And, I started feeling truly successful. It was the ultimate game changer!

If you’re ready to fully embrace the idea that life and business can be (and feel) fantastic right now, you’re in the right place! It's time to DESIGN what you truly want, and on that note, let's explore Design Your Life School™ to see if it's what you're needing right now.

With love,

A Look Inside Design Your Life School ™


Every Month we focus on a community-chosen Design Your Life Topic such as...



Business Growth

Design your business for ultimate growth, scalability and service



Design your mindset for success and release your biggest blocks for good


Wealth Creation

Design your ideal income plan and implement it


Systems & Funnels

Design an optimized experience for your clients and an organized business for you


Personal Development

Design your ideal lifestyle + self-care routines so that you can enjoy life right now

Focus + Productivity

Design your working hours for optimal achievement, income and fulfillment


Planning + Goal-Setting

Design your epic yearly goals with a clear timeline for inspired action and massive momentum

Content + Offers

Design your must-have offers and signature content that your ideal clients can't get enough of

Monthly topics are community chosen.

when you enroll in Design Your Life School, you get a voice in what lessons are created for you so you are always getting exactly what you need most!

Each Month of Design Your Life School Includes...

LIVE Lesson with Cailen

  • Monthly LIVE Lesson with Cailen where she'll walk you step-by-step through that month's Design Your Life lesson

Live Q&A Call with Cailen

  • Monthly Q&A Call with Cailen to get all your questions answered and an opportunity to take the "hot seat" and receive coaching 

Design Your Life WorkBook

  • Every month you'll receive a thorough and beautifully designed workbook that will help you easily take action on that month's lesson

Monthly Calendar

  • Monthly calendar with important dates, action steps and lessons as well as completion times so you can easily schedule everything 

Guided Visualization + Mantras

  • Infuse every area of life with growth by using your monthly guided visualization and mantra cards to ready the subconscious mind for massive expansion

PRivate FAcebook Group

  • Upon enrolling in Design Your Life School, you'll gain access to our private, members-only FB Group where you'll find mastermind buddies, accountability partners, helpful Q&A threads and a community of women who are ready to design their lives on their terms

Built-in Accountability

  • Dedicated accountability partners, community support, group masterminds, co-working hours, email and text reminders and Cailen's on-going support and active participation -- all with the aim of giving you the on-going external accountability you need for internal growth and exponential business development

Already know you want in? 




What Phase of Business Are you in?

Design Your Life School™ is best suited for the Dreamers + Doers (see the chart below if you're confused :-)

Screen Shot 2018-05-10 at 10.20.28 AM.png

So ready to move on to the next Phase of Business?
Design Your Life School will help you do exactly that!

Who Design Your Life School™ is for...


Women in the initial phase of their businesses who are loving (but a little overwhelmed by) all the ideas and options and want a clear plan of action to land their first clients and start bringing in money


Women a little further into businesses who are working all the time and riding the feast or famine roller coaster. Money is unpredictable and you’re questioning “Will it always be like this?”

“Cailen is a gifted coach. She’s been removing the word “stuck” from women’s vocabulary for years and this truly is her zone of genius. If you’re a smart, ambitious and multi-passionate women who’s lacking in direction and clarity, you need to work with Cailen. She’s brilliant and will get you clear on your vision, your mindset and your plan.”

- Janelle Ladewig, Success Coach,

Full Value of Design Your Life School

  • Design Your Life School $1997

  • Private members-only DYL Facebook Group $997

  • Direct Access to cailen $5000

  • Monthly Design Your Life Workbook $900

  • Monthly Design Your Life Calendar $297

  • Guided Meditations, Visualizations + Mantra Cards $97

TOTAL VALUE of this offer $9,288

The values indicated above are based upon 1 year of membership in Design Your Life School.

"Cailen is a beacon of organization, clarity and focus. The franticness and overwhelm that so many aspiring entrepreneurs experience is out the window in a flash, under Cailen's ultra-calm, laser-sharp and capable guidance."

- Liivi Hess, Freedom Lifestyle Business Strategist,

FAQ about Design Your Life School™

How IS DYL School Different from Other MembeRshipS?

Design Your Life School™ is different from other memberships in a number of ways...

(1) Accountability and Action are of the utmost importance to me -- so I've taken extra steps and built-in extra support to ensure you learn, integrate and implement all of the business + life changing content shared within DYL School.

(2) The content is community-driven. Meaning the monthly topics and individual lessons are based upon what the women inside DYL School want and need most.

(3) It's a very affordable price point with a lot of direct access to me. 

(4) DYL School is about more than just building a great business -- it's about creating a fulfilling, fun and meaningful LIFE, too!

What do I Get when I Enroll?

Every month you'll get...

  • 2 LIVE! group coaching calls with me :-)

  • Monthly calendar so you don't miss a thing

  • Monthly workbook, broken down week-by-week

  • Meditation + Mantra cards

When you enroll you gain immediate access to the Design Your Life School™ member portal which houses our monthly lessons. You'll not only have access to our current month's trainings and resources, but as the content library grows, you'll also have access to an archive of past lessons

Is DYL SCHOOL JUst another biz membership that I'll never use but be afraid to leave?

No! Design Your Life School™ is living, breathing community designed to assist in your greatest fulfillment and expansion into the woman and business-owner that you most desire to be. With that in mind, I've taken extra measures to ensure that loads of accountability and feel-good action are baked right in

This means the the lessons are timely but not time-consuming. The content is informative and relevant but not overwhelming and the community is engaged and extremely supportive. And, we also offer additional (as requested) accountability measures like regular inspirational emails and friendly text message reminders to keep your highest priorities top-of-mind.

It's my intention to create an environment in which you feel extremely supported and guided so that you can easily learn, integrate and implement all of the business + life changing content shared within DYL School.

Will Design Your Life School Work for Me?

While there are no guarantees when it comes to programs like this (or life for that matter!), I can say that I've talked to and worked with many, many women who have applied my Design Your Life Process to their lives and businesses, and they all rave about the results they've experienced.

Results like...hiring VAs and childcare support, creating signature programs, enrolling high-end clients, mapping out their biggest business goals, hitting new income milestones, making time for daily meditation and exercise and more! 

The underlying factor is that with Design Your Life School™ you will be taking clear, consistent strides towards creating success on your terms.

If you commit to DYL School, complete your work, and make the most of the support and accountability available to you, I have no doubt that you will experience a real transformation in both life and business.

And, if for whatever reason you feel Design Your Life School is no longer a fit, you can cancel your membership at any time!


All the Design Your Life School™ content is housed within our exclusive members-only portal. It's here that you'll find all the audios, call recordings, worksheets, resources, fillable templates.

All live calls are recorded and will be added to the members-only portal for easy access.

During your membership, you will have access to all of your content within the members-only portal. You will also have the option to download all content so you'll have true lifetime access!

What is the FINANCIAL commitment required?

There are 2 payment options to suit your needs and budget:

(1) ONLY $2.68/DAY!
Join now for just $997 for a full year of membership (with this option, you get 2 months free!!!)

(2) ONLY $3.12/DAY!
Join now for just $97/month (pay-as-you-go, cancel any time -- just give us 1 week's notice before next payment comes due)

And, "grandfathered pricing" means if you enroll now, you'll lock-in this affordable tuition price FOREVER!!! 

Plus, there is a 10-Day Money Back Guarantee with either payment option!

WHat is the Time Commitment required?

Every month you'll receive a Design Your Life Calendar with important dates, lessons and trainings so you can easily schedule everything. Also, included in the monthly workbook are time approximations so that you have a sense of how long each training or lesson will take so you can factor that in, too.

Is there 1x1 Support available?

To ensure your success, I make myself extremely accessible in the Facebook Group and also host 2 live, interactive group calls every single month.

If you'd like deeper 1x1 support, there are 2 à la carte options available to Design Your Life School™ students that you can add on as needed:

(1) You can add on a Jam Session with Cailen (20min mini-coaching session) for $197 or purchase 2 or more for $175/each. Cailen only offers a max of 10 Jam Sessions a month.

(2) You can add on a week of email coaching with Cailen for $97. 

Email for more details or to book either of these options.


Yes! You can either pay yearly or monthly for Design Your Life School™.

When you join now, the monthly membership rate is just $97/month! (FYI -- The full year is $997 which means you get 2 months for free.)

IMPORTANT: There are no contracts. No confusion. Cancel any time.

Why now?

There is no time like the present to Design Your Life!!!

You'll know the "time is now" for Design Your Life School™ if...

(1) You believe 100% in your ability to create your dream life + business.

(2) You're ready for a clear plan, consistent support and the accountability necessary to do it!

...and you’re ready to intentionally design your dream business, your best life, your mindset for success, your growing community, your irresistible offers, your expansive wealth,  your optimal health, and more!!! You’re ready for it all.

"Talent can't be taught, and Cailen absolutely has a natural talent for supporting others in crafting clear visions, seeing what's blocking them, and mapping out the plan to get there.  Many coaches struggle with the planning and systems aspects of business, and that's where Cailen's dedication and natural talents merge, in support of their greatest success."

- Nisha Moodley, Women’s Leadership Coach,


Additional perks when you enroll right now!



Identify your current Phase of Business and get the tools and resources necessary to map out a clear plan for forward motion! [value $500+]

BONUS #2 - Money Clarity Program

Clear your biggest money blocks, tap into your abundance mindset, find your money flow and start making more money than ever before! [value $297]

First Dibs + Discounts

When you become a DYL School student you also get first dibs on 1x1 coaching spots, PLUS amazing discounts on Cailen's popular programs, products and new offers!

Lock-in Pricing

It's just $3.12/day for support, guidance, accountability and coaching! And, when you enroll, you'll lock-in this tuition price forever! No price-hikes ever!!! 


What Design Your Life School ™ members have to say...

Click on the images to scroll through all the posts :-)



Choose your tuition payment plan below

Your tuition will NEVER increase during the lifetime of your enrollment!

Most popular plan!

Best price -- you get 2 months FREE!

No Contracts. No Confusion. Cancel at any time.