Life doesn’t follow a straight line
Some seasons call for a plan.
Others call for triage.
We help with both.
Select Your Path
LifeWise helps your clients or employees move forward whether they’re planning a transition or facing one of life's curve balls.
LifeWise Masterplan™
Planning for an exit or retirement
For business owners preparing for a sale and executives or clients preparing for retirement or a sale, LifeWise Masterplan™ provides the clarity to move forward with purpose.
LifeWise Interrupted™
Support for life’s hardest seasons
For companies and advisors looking to offer tools and benefits that support people through events like divorce, illness, caregiving, or loss, LifeWise Interrupted™ is a human-first solution.
LifeWise™ Blog
LifeWise Masterplan™
What Comes After the Exit? The Title? The Career?
Most people don’t know—and that’s the problem.
Big transitions can leave even the most successful people feeling rushed, lost, or unclear on what’s next.
Whether it’s retirement, selling a business, or a major life shift, the LifeWise Masterplan™ gives business owners and executives the space and structure to plan their next chapter.
Using our proven visioning method, clients map out what’s next across 8 key life areas—so they can make smarter decisions today and build a future they’re excited about.
Ideal for:
Business owners 1–2 years from sale (or recently sold)
Executives approaching or recently retirement
Professional athletes in or post-career
Advisors helping clients through major transitions
Outcomes:
Clear long-term goals in areas like family, legacy, and personal growth
A practical, energizing vision that aligns with financial planning
More clarity, confidence, and meaning in the next chapter
Smart Successful People Still Struggle with What’s Next
74%
74% of business owners who sell their businesses regret it because they lack a plan for life after the sale.
(Exit Planning Institute)
52%
Only 52% of executives feel emotionally prepared for retirement, despite high levels of financial preparedness.
(Edward Jones & Age Wave Study)
5-12 Years
Professional athletes often face financial uncertainty, with many losing their fortunes within 5–12 years of retirement.
(Sports Illustrated, Forbes)
4%
Retirees are 40% more likely to experience depression in the first year of retirement if they don’t have a plan for what’s next.
(Journal of Affective Disorders/Inst. of Economic Affairs)
LifeWise: Interrupted™
When Life Gets Hard, Work Doesn’t Pause—And Support Goes Sideways.
Equip employees and managers with tools to handle life’s toughest moments.
Employee & Manager Crisis Blueprints
Human-first support tools for life’s hardest moments.
When life hits hard—loss, divorce, diagnosis, or caregiving—it doesn’t stay at home.
It shows up at work, impacting focus, communication, and engagement. And it often leaves managers unsure how to respond.
LifeWise: Interrupted brings structure and humanity to these moments.
Employees get just-in-time microlearning.
Managers get practical, compassionate guides.
Companies gain trust, resilience, and retention.
Ideal for:
Companies supporting employees through life disruptions such as
Divorce or separation
Loss of a loved one
Serious illness or diagnosis
Welcoming a new child
Caregiving in the sandwich generation
Managers who want to lead with empathy
Outcomes:
Employees feel seen and supported
Managers lead with clarity and compassion
Organizations preserve culture and reduce productivity loss
LifeWise Masterplan™ for Wealth and M&A Advisors
When clients are clear, plans move faster and deeper.
LifeWise helps your clients define what they truly want—so you can build more complete, aligned financial plans.
Two Delivery Options for Your Clients:
Online, On-Demand Access
A self-guided version that enhances client readiness before planning begins.
Great for offering to clients individually or as part of a multi-client package—helping you streamline discovery and improve goal clarity at scale.
Private 1:1 Experience
A premium, in-depth planning service for high-net-worth clients in transition—like selling a business, retiring, or navigating a major life shift.
Includes customized support, joint planning with a spouse or partner, and tools to guide long-term decision-making.
Why Advisors Partner with LifeWise:
Brings clarity to life goals and transitions
Reduces discovery time and accelerates planning
Deepens trust and strengthens client relationships
Flexible delivery: use with one client or offer across your book
What Clients Receive:
A structured process across 8 life areas
Optional partner/spouse involvement
A customized Decision Compass for long-term clarity
Planning check-ins to keep momentum
About Interwovenly and LifeWise Programs
Built for the Human Side of Change
LifeWise™ was created to fill a gap that most people don’t even realize exists—until they’re in it.
Whether someone is stepping into retirement, selling a business, or facing a personal crisis, they’re often left to figure it out alone. Financial plans, benefits packages, and leadership training rarely cover what lifeactually demands in these moments.
That’s where we come in.
Our tools and programs help people navigate big transitions with clarity, strategy, and support—so they can move forward feeling capable, connected, and clear on what matters next.
Who We Serve:
- Business owners and executives
- Advisors and coaches
- Companies and teams
Our Approach:
- 10-Year Personal Planning and Visioning
- Transition Triage to Quickly Prepare You for LIfe's Curveballs
- Human-First Design, Technology Supported
About Our Founder
LifeWise™ programs are created by Interwovenly founder, Cindy Jennings, a strategist and change advisor with a background in executive coaching, organizational transformation, and personal planning.
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