One Year From Now:

The Residency


a 12-month coaching experience for high impact entrepreneurs

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You ever wonder why doctors go through a residency program?

I mean, they’ve already been through many years of school and practical application… What else is there to learn?

The point of a residency is to give them the space and support necessary to acclimate to their settings & responsibilities as a professional.

The residency is where they grow the maturity and specificity that become the hallmarks of their career.

Similarly, the One Year from Now Residency is about shoring up your foundational leadership and business skills that will ensure a long, healthy career as an entrepreneur. 

At this point in your journey, you already know how to make money. You’ve nailed down the business basics, you’re building out a successful team and you feel good about the results you create with and for your customers.

Now you’re expanding and stretching beyond the necessities and into the previously unimaginable. It’s time to expand into leaving your legacy.

One Year from Now:

The Residency

is a 12-month life + business coaching container for
high-impact entrepreneurs. We create
clear, compelling vision for your life and
work and then bring it all into reality in
one year.

We’re blending sound business strategy,
positive psychology and trauma-informed coaching
practices to help you increase your business
proficiency and mental/emotional maturity.

These tools will allow you to build whatever
the hell you want (highly profitable business
assets, deeply impactful nonprofits,
narrative-shifting special projects…) for the
rest of your life.

It’s about the next 365 days… and every day
of your life after.

Resident visions come to life:

R reimagined common industry practices
from “run-of-the-mill” to “dynamic,
perfectly-suited-to-her/her team’s-skillset-and-desires”
business models that increased profit
margins by a minimum of 20% across all of her
service offerings.

M courageously took a 6 month sabbatical from client work.

They successfully redirected the vision for their company and and returned to the business excited to serve new
clients in a more profitable and sustainable model.

H paid off over $200k of personal debt
while relocating her family to a new city.

They consistently work 15 fewer
hours each week and are expanding into coaching and speaking as a top expert in their industry.

The Details:


All new engagements are a 12 month contract. This ensures you have support for the ups and downs of the entire journey of transformation. Engagements include:

[1 on 1 Coaching] 3, 45-minute solo sessions each month to get specific-to-you support and strategy.

[Community Coaching] Monthly sessions aimed at capturing wins + learnings through our specific evaluation process and live coaching with your peers (entrepreneurs also at the top of their respective industries).

[Bi-annual Live Events] 3-day entrepreneurial adventures that accelerate growth through exploration, creativity and community; complete with live teaching and coaching, bespoke accommodations and unique meal experiences.

[Private Online Community] Access to the private, digital space (Slack) to ask questions, receive bonus trainings, share wins and build relationships with other high-impact entrepreneurs.

Who’s the Best Fit for this?

The entrepreneur who has completed their “act one” of establishing one or more businesses and is ready to move into creating more impact through:

  • Additional streams of income,
  • pivoting into a new industry,
  • growing/expanding the business and changing their role in the organization,
  • successfully navigating major shifts in their personal lives (getting married, divorced, moving, starting or extending their nuclear family, etc.)  
  • Reworking family-business dynamics,
  • Or starting brand new business ventures

Other important notes about you:

  • You are smart, powerful, driven, lead a rich life (you have hobbies and friends and know how to rest), are sharp, energetic, and resourceful as fuck.
  • You have a “I know I am capable of creating anything, but I know support makes things it easier, faster and smoother” attitude.
  • You’re not looking for the “secret sauce” to growing a business, but rather see yourself as a powerful creator – the job of Hailey and the group is to support YOU in your ascend.
  • You like to be challenged, enjoy like learning and are a smidge bit competitive with your self.

The Investment:

12-Months of :

  • 1 on 1 Coaching Sessions
  • Online Community Access
  • Community Coaching Sessions
  • Invitations to live entreprenur adventure events

$30,000 USD OR


We’re going to focus on growing your business proficiency and mental/emotional maturity so that you can build… well, whatever the hell you want for the rest of your life.



Reworking your business model so that income is dependable, sustainable and build for your thriving.


Figure out your exact recipe to double revenue with profitability and personal values intact.


Learning how to plan an exit of a business asset, building a reliable team and replacing yourself.


Become a Beacon in your community, ie; the CEO of your whole life (an efficient decision maker with loads of clarity and self-trust) in a way that serves everyone in your life.


Learn to effectively distribute your time and energy across multiple projects, honoring your humanity.


Step fully into your identity as Entrepreneur (with a capital fucking E), not someone who’s playing at business.

Frequently asked questions

Do I really need to commit to an *entire year* at a time? (Also; “Why don’t you offer smaller packages or shorter engagements?”) 

From the moment you decide you’re a yes to this sort of transformation, your brain undergoes a serious rewiring of seldom reviewed beliefs, habits and behaviors. You will be asked to stretch, try new things, fail bigger and celebrate more deeply. You may shift significant pieces of your business assets to function better, end some and expanding others. You might realize through this work that major pillars in your life need to be torn down and built from the ground up. You will certainly become the most “you” version of yourself that you’ve ever experienced.

For all of these reasons and more, I am completely unwilling to start this process with someone and then abandon them part way through the transformation. So yes, if we go, we go all the way through an entire year. From my work with hundreds of entrepreneurs, 12 months allows all them to be supported through the entire process and leads to the best possible outcomes. 

To be successful, how much time a week should I expect to spend on this work?

I recommend setting aside 2-3 hours a week for attending 1 on 1 coaching calls, group calls and doing your own self- reflection work. Remember, you get out of this work what you’re willing to put into it! I encourage you to show up to the best of your ability.

Tell me more about live events – are there any extra costs?

We will take care of everything besides transport from airport to site and back again and your flight. Everything else; all food, snacks, lodging, etc. is covered. We only ask that you be enrolled and able to complete our Resident Travel Form form at least 6 weeks ahead of the live event dates.

When are community calls scheduled for? 

Monthly group calls are scheduled for the first Friday of each month and will run from 11a-12:30 pm CT. Don’t worry if you miss a call! Those will be recorded and made available in the digital community space.

    What kind of entrepreneurs does Hailey work with?

    This group represents some of the most interesting and impactful entrepreneurs from industries across the business landscape; art, real estate, tech, food, law and more.

    Previous and current OYFN Residents include a tech/UX company, a dual-practice lawyer, an accountant, a co-working company, a private chef, an international real estate portfolio owner, marketers, copywriters and a novelist.

    Each Resident is working on the same thing: Bringing their vision for their next level of impact and profit into reality in a year. 

    Enrollment is open now.

    How does the application process work?

    Click the button a the bottom of the page to be transported to a scheduling where you will:

    • Complete the online application (less than 10 questions) and
    • Schedule your 60-minute application interview with Hailey
    • If accepted (you and Hailey will decide on fit during the interview) in the following 48 hours: 
      • Remit the investment amount
      • Sign the contract
      • Fill out the Resident Questionnaire

    See you on the inside.