"A well-designed life is a life that is generative—it is constantly creative, productive, changing, evolving, and there is always the possibility of surprise." — Bill Burnett

Why not give intentional attention to the life you want?

I was visiting with a client some months back. She felt a job search may soon be required due to corporate shake-ups she was experiencing. We were talking about what she wanted to do with her life. So much of it yet to be lived. She was 45 at the time.

I asked her questions about her work, her life’s desires, and her preferences for her work day. She had taken an array of assessments around skills, tasks, and fulfillment at work. She seemed to be breaking every assessment tool out there. Nothing was helping her.

She entertained taking a call with a career coach. The intake form just felt useless to her. What I discovered about her was something rare in my experience. She had the income she desired and her work was acceptable. As I dug deeper, I learned that work for her was nothing but a vehicle to live her life. She has no real passion for the work she does or excitement about anything that may render a significant wage. Is she happy? Extremely. Does she have friends, a great relationship, meaning in her life, and a healthy mental state? Absolutely.

Her secret? She has designed her life. Work, hobbies, relationships, health, gratitude, forgiveness, and safety, all hold similar rank in her life. She is the most balanced, boundary-driven and healthy person I know.

A great place to get started in life design is with the work of Bill Burnett. Bill is the author of Designing Your Life: How to Build a Well-Lived, Joyful Life. Bill Burnett is the Executive Director of the d.school — Stanford University's renowned design program. Alongside co-author Dave Evans, he took the rigorous, iterative methodology of product design and applied it to the most important project any of us will ever take on: building a life.

There's a moment that sneaks up on most of us somewhere in our fifties. It's not dramatic. It doesn't arrive with a crisis or a doctor's call. It just shows up one morning between the second cup of coffee and the commute as a quiet, nagging question: Is this it? Is this what I actually chose, or is this just what happened?

For most people over 50, life has been a long series of reasonable decisions. You picked a career that made sense. You raised kids, built routines, paid mortgages, showed up. And somewhere in the doing of all that, the designing got skipped. Not of this was because you were careless. It is because nobody ever told you life was something you could prototype.

Bill Burnett wants to change that. And he has the receipts to prove it works.

The book, Designing Your Life: How to Build a Well-Lived, Joyful Life, became a cultural phenomenon — a New York Times bestseller that transformed how people across generations think about career transitions, purpose, and what Burnett calls "the well-designed life." A life, he argues, that isn't discovered through soul-searching or waiting for a sign but built through curiosity, experimentation, and honest self-assessment.

The methodology is rooted in design thinking: a framework developed in engineering and innovation labs that emphasizes iteration over perfection, prototyping over planning, and evidence over assumption. Applied to life, it becomes something radical and remarkably practical.

"A well-designed life is a life that is generative — it is constantly creative, productive, changing, evolving, and there is always the possibility of surprise." — Bill Burnett

What makes Burnett's approach particularly compelling for the 50+ audience is what it does NOT ask of you. It doesn't require you to quit your job, find your passion in a weekend retreat, or reinvent yourself with some dramatic pivot. It asks something harder and more honest: that you pay attention to what's actually working, release the dysfunctional beliefs about how life is "supposed to" go, and begin, right now, building the next version on purpose.

THE DYSFUNCTIONAL BELIEF THAT TRAPS THE 50+ PROFESSIONAL

Burnett identifies a category he calls "gravity problems" — beliefs that feel like immovable facts but are actually just assumptions masquerading as constraints. For the over-50 crowd, gravity problems are everywhere.

"It's too late to change."

This is perhaps the most corrosive story in the 50+ narrative. The data doesn't support it. Burnett's own research, and decades of adult development psychology behind it, shows that people in their 50s and 60s are often at their most capable, emotionally regulated, and strategically clear. The issue isn't capacity. It's permission. Most people over 50 are waiting for someone to tell them it's okay to want something different. Burnett's answer: stop waiting.

"I need to figure out my passion first."

This is what Burnett calls the "passion hypothesis"; the belief that somewhere inside you is a singular calling waiting to be unearthed, and until you find it, you can't move. He is blunt: most people don't have a pre-existing passion. Passion, more often, follows engagement. Not the other way around. You don't find it. You cultivate it, through doing, trying, and paying attention to what generates energy versus what drains it.

"I've already invested so much — I can't walk away now."

This is the sunk cost fallacy wearing a life story. Burnett calls it "the anchor problem." The years you've spent in a career, a role, or a pattern are not a reason to stay. They are simply context. The question isn't what you've done. It's what you want to build next, and whether your current path is a runway or a rut.

FOUR TOOLS THAT WORK FOR ANYONE OVER 50

Burnett's design toolkit is deceptively simple. But simple is not the same as easy and for a generation that has spent decades executing rather than reflecting, these practices require real commitment.

1. The Work/Play/Love/Health Dashboard

Before you redesign anything, you have to know where you actually stand. Burnett's dashboard asks you to rate four core areas of your life, Work, Play, Love, and Health, not against some idealized standard, but against your own felt sense of fullness. The exercise often reveals that people who feel stuck are actually quite full in some areas and running on empty in others. It's a diagnostic, not a judgment. The goal is clarity, not comfort.

2. Good Time Journaling

This is the practice of tracking, for at least three weeks, which activities during your day generated energy and engagement (flow states), and which drained you. The journal becomes evidence. And evidence, unlike vague feelings, is actionable. For the 50+ professional, this practice frequently surfaces a sharp and useful truth: the things that once energized you may no longer, and the things you've dismissed as "hobbies" or "too late to pursue" may be precisely where your next chapter lives.

3. Mind Mapping

Once the journaling surfaces your energizers, mind mapping lets you follow those threads outward. You begin free-associating around what excites you without censorship or practicality filters. The goal is divergent thinking: generating many possible directions before narrowing. Most people over 50 have been in convergent mode, narrowing, prioritizing, deciding, for so long that expanding the field feels unnatural. Burnett calls this essential. You cannot design something you haven't imagined first.

4. Prototyping: The Life Design Interview and the Odyssey Plan

This is where design thinking gets most distinctive and most useful. Rather than making a big decision about your next chapter, Burnett advocates prototyping it: having "life design conversations" with people actually living the life you're curious about. Not informational interviews for jobs. Genuine curiosity conversations about how others built what they built. Then, he asks you to sketch not one but three distinct "Odyssey Plans",  three radically different versions of the next five years of your life. Each with its own timeline, questions it would answer, and confidence rating. The point is not to pick one. It's to break the tyranny of the single path.

"You cannot connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect." — Steve Jobs, as quoted in Designing Your Life

WHY THIS MATTERS MORE AFTER 50

Here is the counterintuitive truth that Burnett's work keeps surfacing: the 50+ professional is often better positioned for intentional life design than anyone younger. You have something younger people don't — a long track record of yourself. You know what environments drain you and which energize you. You know which relationships have mattered and which were noise. You have pattern data that took decades to accumulate.

What's often missing is not self-knowledge. It's permission to act on it.

Burnett's framework gives you that permission, not as a feel-good affirmation, but as a structured process. It replaces the anxiety of open-ended reinvention with something you can actually execute: a series of small, low-risk experiments that generate real data about your next chapter.

For those of us in industries like field marketing, beverage alcohol, hospitality, or agency work, industries where the pace is relentless and the work identity runs deep, the design mindset is especially powerful. Because it doesn't ask you to abandon what you've built. It asks you to look at it honestly and decide: what's worth keeping, what's worth redesigning, and what deserves to be prototyped from scratch?

THE REFRAME THAT CHANGES EVERYTHING

Perhaps the most powerful shift in Burnett's entire framework is this: life is not a problem to be solved. It is a design challenge to be engaged.

Problems have solutions. Design challenges have iterations. And iterations — small, intentional, curious steps are available to anyone at any age, in any circumstance.

The 50+ professional who picks up this framework doesn't need a blank slate. They need a sketchpad. Not to erase what's been built, but to draft what comes next, deliberately, energetically, and on their own terms.

Burnett's final provocation is worth sitting with: most people spend more time planning a two-week vacation than they spend designing the life they live the other 50 weeks of the year.

You have time. You have data. You have more capability than you're probably giving yourself credit for.

The only question Burnett really asks, the one that sits underneath every exercise, every journal entry, every prototype, is the simplest and most demanding one of all:

What kind of life do you actually want to be living? And what's one small thing you could do this week to find out?

If you need assistance or want to discuss anything listed above, schedule a call.

Thanks to our sponsor. Nokbox: A system designed to keep life organized, even when things get chaotic. NOK stands for Next of Kin, and NOKBOX help you organize important documents, accounts, possessions, and estate details so your next of kin knows exactly what to do in something happens.

But it’s not just for the future. NOKBOX gives you peace of mind now by keeping everything in one organized place, saving time, reducing stress, and making it easy to find what you need when you need it.

Check them out below and invest in a NOKBOX for you and your family.

I met Nisey in December 2025 through conversations with a variety of Over 50 Pros. 

Nisey Woods is a SAG-AFTRA actress based in Atlanta, GA. Her résumé includes performances in productions like The Vampire Diaries (2009), Open (2020), and Gray Hairs per IMDb. Behind-the-scenes content on her site shows on-set moments, collaborations with other artists, and her perspective on life as a creative. You'll learn much more as you read through the interview. 

Her Backstage history highlights skills including comedy, physical comedy, music production, improv, construction, event management, promo work, and much much more.
Nisey's energy is infectious and her insights and experiences serve to inspire anyone who is seeking to sign the front of the check instead of the back. 

Q: Can you share a bit about how your journey into acting and entertainment began? Are there elements you are still excited about today?

A: Wow, I love this question.  

I grew up thinking I wanted to go to law school (my dad was an attorney, and yes, I  heard a lot of lawyer jokes during my youth…Why don't sharks bite attorneys? Professional courtesy.)  My dad was a good guy who showed me the importance of volunteering and pro bono work.  

The product of divorced parents and living with my dad, I spent a lot of time in his office after school (it was super fun to use the copier and lots of office supplies to make crafts).  And, I quickly learned that I didn’t want to have anything to do with law.  I saw how taxing it was on my dad; how he didn’t get to spend as much time as he wanted playing the piano (he had perfect pitch since age 4 and played like Chopin), or coaching my brother in soccer, or talking with my super intelligent big sister about things I didn’t yet understand, and how there was always that additional family member at the dinner table: the dreaded yellow legal pad.  He worked so hard for his clients, at the expense of family time.  

My next brilliant idea was that I would join the army (my dad was a Lieutenant Colonel in the army, and while living in Germany, was a Judge Advocate General).  I have a natural gift of order.  My dad said I would always organize my toys instead of play with them.  I would have my bed made so well you better believe that coin would bounce right off of it.  

To this day, I’ve only been late once to work, by two minutes, and that was after I changed a flat tire.  My life is labeled and alphabetized.  Perfect army material, right?  When I told my dad I wanted to join, he looked at me with a look I will always remember and can’t begin to describe, and simply said: “No you don’t.”  And that was that.

So, off to University I went, using my academic scholarship (I was the class Valedictorian, which made my dad so proud!) clueless as to what I wanted to do with my life.  Then I saw a class that caught my eye: “Writing For Radio.”  

I took it as it sounded like it would be fun, and I needed a fun class since I had been taking my required courses for two years, just cranking them out.  I enjoyed the class.  Then I saw another class: “Basic Video Editing.”  I took it.  I loved it.  Then “Advanced Video Editing.”  Yep, you guessed it…I was hooked.  

Before you knew it, I was interning at a small local TV station with a Kick Ass (can I say “ass?”) Boss Lady, Byron, who saw my creativity and encouraged the heck out of me.  I was operating cameras, I was editing, I was segment producing, I was hosting, I was doing voice over work, I was technical directing live tv shows, I was doing whatever I wanted to do because Byron believed in me, and then I believed in me.  

I was encouraged to enter some of my edited work into contests, winning them (one little contest you might have heard of earned me an Emmy award while I was still in University).

When I graduated from University (Communications Multi Major with a minor in Technical Communications), I was hired full time, on a freelance basis, at the TV station.  This was like having a copier and office supplies on steroids!  

Being lost and not knowing what to do, well, that is how it all started.  And that’s just the beginning.

Are there elements that I’m still excited about today?  ABSOLUTELY!  ALL OF THE ELEMENTS!  I have been working in the TV & Film industry since 1991.  My own jaw still drops at the thought of the experiences I’ve had because of my unexpected career that I had no idea would bless me so much.  I often catch myself saying “I’m so lucky.  I am so very lucky.”  

The locations I’ve filmed at, the people I’ve worked with, the destinations I’ve traveled to, the sets that I’ve been in…never in my life would I have dreamed that such magical experiences would be part of my life.  And I get paid for that?  Say what?

Q: Your résumé includes TV, film, and on-set work — how did you navigate the transition between different types of performance work?

A: There really isn’t a difference between the different types of performance work, and the crews & equipment are mostly the same.  I am either in front of the camera (or audience, in theater) or behind the camera.  

At the end of the day, the goal is the finished product.  Everything is crafted for audience enjoyment, which is absolutely thrilling to be a part of creating!  

Q: What does being a creative professional over 50 mean to you personally?

A: Growing up, I had Superhuman Women in my life that were my role models: my Great Aunts, my Grandma, my Great Grandma.  Their years of birth range from 1866 – 1912, and they were all over 50 when I was born.  

I was surrounded by these Power House Beings, watching them do incredible things (carpentry, custom dress making for clients, volunteer work, rising in the ranks of the Navy, car repair, shoe making, Michelin Star worthy recipe creation – just to name a few!) all while tending to our large family, managing everything.  

They Were Unstoppable.  They had to be given the time in which they lived – through wars, The Great Depression.  So, to me personally, being a Creative Professional Over 50 is a Tribute To Them, My Heroes.  My first teachers.  My first look into what’s possible, no matter your age.  They all kept going, full throttle, until their death (average age of death: 99).  

Q: Acting and entrepreneurship both require resilience and adaptability. What skills from your acting career have helped you in entrepreneurial or promotional work?

A: “I must be like water, else I snap and break.”  Bruce Lee

Acting requires Authenticity.  Awareness.  Letting Go of The Self, of The Ego.  I have worked so hard on auditions over the years.  The formula is: every 100 auditions results in 10 callbacks, and from that, 1 booking.

Countless times I’ve heard the silent word “No” (a lot of actors take that as rejection).  I look at it as excitement as that means the Director found the perfect person to execute their vision, and that is to be celebrated!  

When I’m doing promo work, there are a lot of people that say “No” to sampling the product that I’m demoing, or to making a purchase.  Again, another celebration as people know what they prefer, and have the confidence in sticking to it!  

I never take it personally as I too have my own preferences (sourdough bread over French bread always!).  There are 8.4 billion people on the planet – is it really worth it to take it personally when a few of them say “No?”

Q:  As someone with a diverse set of skills (e.g., improv, music, comedy, construction, sales), how do you decide what opportunities to pursue next?

A: “The most important thing is to keep the most important thing the most important thing.”  Jim Kwik, Brain Coach & author.

My health and that of my doggie boy Cobi are the most important thing.  My body is the only home I have to live in, so without it, I am of no good.

I recently started my own business, Build & Bloom LLC to build single family homes with integrity, in Georgia.  My business grew out of my love of construction, which I’ve had since I was a little girl.  I thank my mom for all those trips to the hardware store, and showing me how to do things like sweat weld, electrical repair, pouring concrete, framing.  
There wasn’t anything my mom couldn’t do!  I have completed 3 full rehabs, including my home in which I currently live, and which has been used as a location for TV, movies and music videos (super cool, and makes me proud!).  I often have flashbacks to my childhood where my mom is rockin’ some amazing tool, and then Voilà, something stunning emerges.

I get such a charge, creatively, when I get to work on construction projects (I often stop at other construction sites as I just can’t help myself; I drool).  Building a home is like creating an amazing piece of art, living art, in which families can thrive!

I also continue with my acting & music gigs, my promotional work, and my volunteering. All of this is important to me.  There is Invisible Teamwork happening, constantly, that I benefit from.  

What I mean is, there are literally a zillion things happening every moment that have nothing to do with me, yet everything to do with me.  They are out of my control and yet play an important role in what opportunities I pursue next.  

For example, I might apply for an acting gig or a promotional gig that has moved me in some way, be it the character or the product.  I might not get any of the gigs, and then another opportunity will pop up that will come to fruition.  

I trust that All Is In Divine Order; that what is for My Highest & Best Good will happen.  I lean into my Buddhist Faith and don’t get attached to any outcome.  As singer Jelly Roll so beautifully sings in his song ‘Son of a Sinner:’  “I took the rearview off of this old Ford so I only see in front of me.”  Keep it moving baby.  Keep it moving.

Q: Do you think age brings an advantage in creative work? If so, how?

A: YES!  Something rooted deeply in me switched when I turned 50, almost 5 years ago.  Something amazing, beyond expressible.  It was as if I became a Jedi (noble order of Peacekeepers in Star Wars), a fox (widely regarded with intelligence, and adaptability; known for being strategic, foxes use these traits to thrive in diverse environments) and part Mother Nature, who to me, is the most Creative of All.  Author Michael Singer said: “If you keep letting go of who you’re not, you will end up who you are.”  

So, I am JediFoxMotherNature, not giving a toot about what others think (please understand that I intend for this to be polite and encouraging, not crass).  

Age has taught me to continue to color outside the lines as it Frees My Soul.

Q: What’s one belief you’d tell other professionals over 50 to let go of?

A: The belief that you have nothing to offer.  All of us over 50 have POWERFUL VOICES that NEED TO BE HEARD!  Don’t you dare silence yourself.  Take a look at your life with the wonderment & curiosity of a child, and then you will truly see how Phenomenal You Are.  Others are lucky to be in your presence.  Give of yourself freely.

Q:  If you could share one defining piece of wisdom with the Over50Pros community, what would it be?

A: BEING OVER 50 IS A SUPERPOWER!  Actress Kathy Bates stars in the TV series Matlock.

These lines said by her character Matty sum it up: “You see, there’s this funny thing that happens when we women age. We become damn near invisible.  People assume I’m a harmless old lady.  It’s useful.  Nobody sees us coming.”  

Share who you are with the World.  You have incredible insight that ONLY YOU CAN OFFER!  Your knowledge is worth more than gold, so get out there and share it.  Google has nothing on you.  You Rock.

Q: Is there a legacy you hope to leave — either through your art, your mentoring, or your professional journey?

A: The earth has been around for 4.54 billion years.  I’ll be on it for around 99 years.  I keep it in perspective.  So my legacy that I hope to leave is more of a daily legacy, and that is to shower people with Sunshine.  Bring about Smiles and Love.  That’s it.

Learn more about Nisey and her work with Build and Bloom and other cool projects below. A Build and Bloom Site is forthcoming and will be shared in upcoming editions!
https://www.niseywoods.com and https://www.theyellowhouseatlanta.com.

Oh, that’s funny - Corporate jokes from Michael Kerr

If you’re still signing the back of the check - This may be useful

Get ready for that accountant! - IRS resources for Small Biz

Best time waster of the week - Look out other peoples windows. World over!

100 year old Jocleta Wilson working at Home Depot

These 200 cities have the unhappiest workers in the US

Too old to launch a business? Science says think again.

Our Conversation with Marketing Genius Elliott Cunningham

You’re doing $15 tasks with $150 talent.

Get paid to be you!

A free seven day challenge program that gets you reconnected with your network. Less than 10 minutes a day. Click Here

I’m designing my life. I hope you are designing yours.

The biggest takeaway for me in reading Bill Burnett’s book and other works around life design is this idea: It’s up to me. I just have to give myself permission.

I’ve lived by and through the expectations of others my entire life. It’s likely, most of you have as well.

Let’s stop. Let’s assess what makes us happy and pursue that. I watched Warren Zevon’s last visit with David Letterman recently after having heard the visit referenced on a podcast. Warren had little time left having been dealt an advanced cancer diagnosis. When David Letterman asked what the illness had taught him about life and death, Zevon replied:"How much you're supposed to enjoy every sandwich." Visit the show here and start designing your life.

And as always, if you need help with anything related to topics in the newsletter or transition over 50 years old, schedule a call.

We are proud to share Prairie Growth Solutions as a pathway to starting a business coaching practice. This is not a paid sponsorship, but instead a recommended pathway to exit corporate life. The support systems, tools, and client support is tremendous. Click here to learn more.

Please click below and tell me what you like or dislike about the Front of the Check newsletter and how I may deliver more value to you! You are my growing community and I want your feedback. I’ll Venmo or Zelle you $5 for two minutes of feedback.

Click Here for Feedback Form

Coming Next Week: Building Trust in Yourself