What Matters Most 365: Life By Design® FAQs

Q: How would you describe What Matters Most 365: Life By Design®?

Q: Is this a group program?

Q: What if I want to go through What Matters Most 365® with a friend?

What Matters Most 365 FAQs

Q: Is What Matters Most 365: Life By Design® a one-time program?

Q: What’s covered during each week of the program?

Q: Does this life design program include one-on-one coaching?

Q: What happens during the weekly Support & Accountability calls?

Q: Is what I share with you during the program confidential?

Q: Will What Matters Most 365® help me find a new job?

Q: I work 9-5. How will I be able to schedule the weekly calls?

Q: What if something comes up and I need to reschedule a call?

Q: What if I miss a session?

Q: Do you only work with clients in Ann Arbor?

Q: What if I want to meet in person for our weekly Support & Accountability sessions?

Q: I have a vacation coming up. How can I start the program now but take a break while I’m on vacation?

Q: How do I know if I’m a good fit for the program?

Q: What’s your coaching style?

Q: What if I want ongoing support after the 4-week program?

Q: I don’t know what I want to be “when I grow up”. Will your program help with that?

Q: Who signs up for this program?

Q: What if I’m not satisfied with the program?

Q: What is my investment for the 4-week program?

Q: What payment methods do you accept?

Q: How do I get started?

Q: If I’m not quite ready to take the plunge and enroll, how else can I stay in touch with you?

Q: What if my question isn’t addressed here?


Q: How would you describe What Matters Most 365: Life By Design®?

A: What Matters Most 365:  Life By Design® is wake-up call for your life. This program is all about intentionally designing your next 365 days by clarifying what you really (really!) want, embracing who you are, and designing a transformational plan for making the next 365 days your best yet.

Q: Is this a group program?

A: No, this is one-on-one personalized interaction—it’s just you and me working together! I’ll be alongside you throughout the 4 weeks as your coach, thinking partner, and cheerleader—offering you personalized encouragement, support, and accountability as you intentionally design your life.

Q: What if I want to go through What Matters Most 365® with a friend?

A: Great idea! I frequently have two or three friends sign up for the program at the same time. Keep in mind What Matters Most 365: Life By Design® is a one-on-one experience. While you and your friend(s) will go through the program separately and each have individualized Support & Accountability sessions with me, the camaraderie you experience can be an added boost of support and motivation.

Q: Is What Matters Most 365: Life By Design® a one-time program?

A: Many enroll in this life design program annually, which allows them to create a new plan for the next 365 days—while continuing to benefit each year from the program’s structure, support, and accountability. Others enroll in the program once and then take a self-directed approach to their subsequent annual life planning.

Q: What’s the focus during each week of the program?
A: Below is a brief look at the focal point of each week, and you can visit my website for a detailed description of what the program entails.

  • Week #1: Current Landscape: Where you are, what’s working and what’s not
  • Week #2: Who Are You? Owning your strengths and living your values
  • Week #3: Dreaming + Goal Setting = Turning your vision for the future into reality
  • Week #4: Tactical Drill Down: From wishful thinking to action

Q: Does this life design program include one-on-one coaching?

A: Yes, this 4-week program includes 4 one-on-one Support & Accountability coaching calls. In advance of each call, you complete 2-3 hours of pre-work. You then call weekly for your 45-minute personalized Support & Accountability coaching session with me to apply Life By Design concepts to your life in real, meaningful, and lasting ways.

Q: What happens during the weekly Support & Accountability calls?

A: I’m your thinking partner and advocate on these calls as we debrief the week’s exercises. During these coaching calls, you’ll extract insights to begin constructing a blueprint for intentionally designing your life. Sometimes I’ll facilitate a quick exercise to bring the week’s topic into even greater focus. We’ll wind down each call with key takeaways to help synthesize your insights from the week’s assignment and coaching session. The call will conclude with a preview of the upcoming week.

Q: Is what I share with you during the program confidential?

A: Absolutely! I will not divulge to anyone you are enrolled in What Matters Most 365: Life By Design® or the content of our work together. Whenever data related to What Matters Most 365® is compiled or published, all identifying data is either eliminated or changed.

Q: Will What Matters Most 365® help me find a new job?

A: A critical component of any successful career transition is asking and answering the question: Who am I? Your answer primes you to find a job, career, or calling that’s truly a fit and brings satisfaction, engagement, and success. Through What Matters Most 365: Life By Design® you’ll gain clarity about Who you are so you can pursue a career that’s in alignment.

Q: I work 9-5. How will I be able to schedule the weekly calls?

A: I have evening hours available on Wednesdays. If that time slot doesn’t meet your needs, let’s talk and see what will. Don’t let concerns about scheduling prevent you from actively and intentionally designing your life! We can find a way to make it work.

Q: What if something comes up and I need to reschedule a call?

A: If you need to reschedule a session, you’ll click on the link provided in your original appointment confirmation email. Appointments can be rescheduled up to 2 hours prior to a session, but I appreciate 24 hours notice, if possible.

Q: What if I miss a session?

A: Sessions may be rescheduled in advance. Sessions altogether missed without rescheduling will not be made up. Instead, you will advance to the next week’s pre-work and call.

Q: Do you only work with clients in Ann Arbor?

No! Because this is a virtual program conducted by phone, there are no geographic barriers. I have clients all across the U.S. and even in Canada and Europe.

Q: What if I want to meet in person for our weekly Support & Accountability sessions?

A: While I appreciate the desire to meet in person, all Support & Accountability sessions are conducted by phone. This allows me to work with people all over the world, and it relieves you of the chore of driving through traffic to get to your appointment, finding parking, etc. I encourage you to consider these advantages of phone coaching:

  • Concentration—we can both enjoy greater concentration without the drawback of visual distraction
  • Convenience—you can call from home, office, or any distraction-free location that provides privacy and quiet
  • Easier to ‘Open Up’—a blend of anonymity and intimacy comes from telephone coaching that helps you open more fully to the coaching process
  • Time Efficient—there is no traveling involved, which allows phone coaching to fit into the busiest of schedules

Q: I have a vacation coming up. How can I start the program now but take a break while I’m on vacation?

A: Because I know life is busy and the unexpected happens, you have a one-week grace period to complete the 4-week program. At the start of the program I’ll let you know the deadline for completing your 4 sessions based on the date you enroll.

Q: How do I know if I’m a good fit for the program?

A: On the one hand, I know you’re a good fit for the program because everyone can benefit from intentional life design. Life is short and this is not a dress rehearsal, so it makes sense to step up and design your life so you can truly thrive. More specifically, you’re a good fit for the program if you are willing to devote the time and space in your life to complete 2-3 hours of pre-work each week and be fully present and engaged during the Support & Accountability coaching sessions.

Q: What’s your coaching style?

A: As your coach, I’ll be your thinking partner and advocate—someone who is 100% focused on you and your success. While always empathetic, I have a straightforward, no‐nonsense style. I’ve been described both as an encouraging thinking partner and a kick-in-the-pants advocate. I will ask you not to stay stuck, look too long in the rear view mirror, or think small. I will ask you powerful and insightful questions in order to: clarify your goals, remove the obstacles to what you really want, and eliminate the heavy costs of thinking small and defining your success too narrowly. We will not be a good fit if you focus on blaming others, are in a perpetual state of complaint, gravitate toward suffering, want to continue selling yourself short, or refuse to take action.

Q: What if I want ongoing support after the 4-week program?

A: To live the coming year based on what matters most, it’s critical to check in regularly to reconnect to your goals, recalibrate as necessary, and recommit to what matters most for a breakthrough year. Some of my clients prefer doing this on their own and use the 4Rs (Right Questions to Reconnect, Recalibrate, and Recommit) to provide structure. Others know they could use additional support and accountability, which is why I offer ongoing coaching packages. You’ll learn more about 4Rs Coaching, which is only available to those who have completed What Matters Most 365: Life By Design®, at the end of the 4-week bootcamp.

Q: I don’t know what I want to be “when I grow up”. Will your program help with that?

A: What Matters Most 365: Life By Design® is a means for getting to know yourself better—both who you are and what you really want. Knowing who you really are (not who you were 5 or 10 years ago or who you think you should be) and knowing what you really want (free of shoulds, have-tos, and others’ expectations) are critical first steps to knowing what you want to be “when you grow up”.

Q: Who signs up for this program?

A: My clients are diverse; I work with men and women of all ages and walks of life, from entrepreneurs to corporate employees, from homemakers to retirees. My clients are located in big cities and small towns throughout the U.S., Canada, and Europe. While demographics are varied, they all have in common a desire to intentionally design their lives. For some, this life design program is the kick in the pants they need to get unstuck and unstalled. For others, it’s about expanding what’s possible and taking life to the next level.

Q: What if I’m not satisfied with the program?

A: I offer a no-hassle money back guarantee because I’m confident you’ll find What Matters Most 365: Life By Design® to be a life-transforming experience. If for any reason you’re not entirely satisfied, you’re welcome to a 100% money back guarantee within the first 2 weeks of the 4-week program. All you have to do is ask and your money will be refunded, with no hassle or delay.

Q: What is my investment for the 4-week program?

A: Your investment for the 4-week bootcamp is $449.

Q: What payment methods do you accept?

A: You may pay using Visa, MasterCard, Discover, American Express, or your PayPal account. For those who do not use PayPal or credit cards, I will accept payment by check.

Q: How do I get started?

A: When you’re ready to get started, visit the What Matters Most 365: Life By Design page and click on the red Book Now button located on the right side of your screen. That will take you through the steps to process payment and schedule your first Support & Accountability session. Upon receiving notification of your enrollment, I’ll send you an email to kick off the program that includes the first week’s pre-work along with details about scheduling your subsequent sessions.

Q: If I’m not quite ready to take the plunge and enroll, how else can I stay in touch with you?

A: If you haven’t already, I encourage you to stay in touch by signing up for updates.  As a subscriber, you’ll get ideas, inspiration, and insight—as well as the occasional kick in the pants. You can also connect with me in other ways, including:Let's connect!

Q: What if my question isn’t addressed here?

A: If you still have questions about What Matters Most 365:  Life By Design®, please feel free to email me at Jennifer@GraceStreetGroup.com.