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.
Whether it’s retirement, the sale of a business, or a major shift in identity, big transitions can leave high-achievers feeling lost, rushed, or unsure of what’s next. The LifeWise Masterplan™ gives business owners and executives the space and structure to figure it out—before or after the change happens.
Using our proven 10-Year Visioning method, we help people map out their next chapter across 8 key areas of life—so they can make better decisions today and create a future they’re excited about.
This service is ideal for:
- Business owners within 1–2 years of selling (or post-sale)
- Corporate executives approaching or exiting retirement
- Professional athletes curing or post-career
- Wealth managers and M&A advisors supporting clients through transitions
Outcomes:
- Clear long-term goals across 8 key life areas like: family, adventure, legacy, and personal growth
- A practical, motivating vision that aligns with financial planning
- Stronger confidence, less regret, and a more meaningful 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 an employee is hit with a major life event — a loss, divorce, diagnosis, or caregiving crisis — it disrupts more than just their personal life. It impacts their ability to focus, communicate, and stay engaged at work. And it can leave their managers unsure how to help — or what to say.
LifeWise: Interrupted helps companies and advisors bring humanity and structure to these moments. With just-in-time microlearning for employees and conversation and perfromance management guides for managers, it’s a benefit that builds trust, resilience, and retention.
This service is ideal for:
- Mid-sized companies that prioritize employee support during life disruptions
- Managers who want to lead with empathy and effectiveness
- Wealth advisors with clients going through personal disruptions
Use cases include:
- Divorce or separation
- Death of a loved one
- Serious illness or diagnosis
- Welcoming a new child
- Sandwich generation caregiving
Outcomes:
- Employees feel seen and supported during difficult seasons
- Managers have clear, practical tools to lead with compassion
- Organizations strengthen culture while reducing productivity loss
LifeWise Masterplan™ for Wealth and M&A Advisors
Plans sharpen and deals close faster when clients know what they want.
LifeWise brings personal clarity—so you can do what you do best.
Our Partners Include:
- Wealth Managers
- M&A Advisors
- Business Coaches
- CPAs and Tax Advisors
- Estate planners
Why Partner with LifeWise?
- Strengthen trust and deepen relationships
- On-demand, self service or 1:1 personalized program formats
- We deliver the tools, you stay the trusted guide
What Your Clients Receive From LifeWise Masterplan™:
- Structured visioning for life after business or career
- Joint planning with a spouse or partner
- A custom Decision Compass for better choices
- Progress check-ins over time
From LifeWise Interrupted™:
- Microlearning and mindset tools during life events
- Conversation guides for clients and advisors
- Just-in-time, real-life support for every kind of life curveball
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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