We recently had the chance to connect with Jen Swindler CFP®, CDFA®, AFC® and have shared our conversation below.
Jen, really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: What are you most proud of building — that nobody sees?
It’s common for others to see someone starting and building a business and to think the business itself is the whole goal (a profit-generating one, more specifically). But the thing I most hope to create is a feeling, something intangible, something buried underneath all the day-to-day logistics and necessary work behind my financial planning practice.
I want to build a place where people can be open about their finances and the humanness that went into every decision (good or bad) and not feel judged after everything is laid out on the table. I want the conversations I have with every potential client, past client, and future client to have a ripple effect; I want the feeling they get from our conversations to spill over into additional open conversations about money with a friend or a partner or a parent.
Money is still our society’s biggest taboo, and we’re far from aware of the negative effects it can have on us. Financial shame is unbelievably common, and it seems like almost everyone feels like they’re a little bit more behind than everyone else is. But the thing is, most of us don’t have everything figured out. Most of us are uncertain about both our present and future day financial situations. But the benefits of speaking openly about money are vast — they can result in better jobs, better compensation, better decisions, and less shame. And I hope that my work can continue to be an influence in that.
Can you briefly introduce yourself and share what makes you or your brand unique?
My journey into financial planning began while I was working as a self-employed artist & graphic designer; learning to manage my own finances and variable freelance income is what sparked my interest in understanding money better. This quickly became more than a side hobby, and eventually resulted in my making a career change to pursue an undergraduate degree in financial planning. I later went on to complete a graduate degree in Financial Planning & Analytics. In addition, I obtained the Certified Financial Planner (CFP®) designation, am an Accredited Financial Counselor (AFC®), and a Certified Divorce Financial Analyst (CDFA®).
As a free-spirited, artsy feminist working in the financial planning industry over the years, I never quite fit into the old-school, male-dominated industry (very much in need of diversity and new perspectives). Eventually, I decided I needed to create the space I was searching for. I started Money Illustrated with the hope that I could bring my two worlds of art and financial planning together in order to create something different—an inclusive, progressive, and innovative approach that’s both creative and human-centered. My goal is to always act in clients’ best interest, while guiding toward financial success and educating on the intricacies of their financial situations. Overall, I want to help others feel empowered to live their dream lives.
No matter what your financial background looks like, I’m here to offer a judgment-free approach that meets you where you are. Financial planning is a tool to help you build a life that feels like your own, focusing on your values, supporting your relationships, and prioritizing what truly matters most to you.
Outside of personal finance, I love to hike in the nearby Rockies, tend to my plants, practice yoga, and paint. I live near Salt Lake City, Utah, with my exuberant dog and two cuddly old cats.
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What breaks the bonds between people—and what restores them?
I think what most breaks the bonds between people is the illusion of separateness. I love the analogy of humanity being like a vast puzzle, each one of us a single piece of the whole picture. When we have conflict and can’t see from another’s perspective, we tell ourselves (consciously or otherwise) that we’re different from one another. We see our disagreements as the puzzle piece’s edges delineating us from the people who disagree with us, but if we could just get to the root of the emotions and experiences behind our perspectives, we’d see that they’re not so different. We’d see the way our edges perfectly match up with one another’s.
For me, remembering we are all the same is the solution. We all generally want the same thing underneath all the specifics that might appear different on the surface; but below the surface, don’t we all just want to be loved, to love, to be happy? I think it’s all simpler than we make it out to be sometimes.
What’s something you changed your mind about after failing hard?
I want to share a poem I wrote on this, if that’s okay! It’s about the ways our failures, suffering, and trauma keep us from living life to the fullest. But I am a firm believer in being able to overcome anything. We don’t have to be held back forever because of something that happened in the past.
Falling and flying
She found joy in a handspring,
In flying through space,
Jumping a trampoline,
Free and weightless.
Though gravity came for her,
Time and again
Whenever she’d fall,
She would get up again.
One day tried to float
And the earth broke her fall
And with it, her bones —
Broken, she thought,
“Perhaps I’m not meant
To fly high after all.”
But the heights kept on calling,
Saying, “Meet us up here!
You’re meant for the sky,
Just let go of your fear.”
So she gave it a try,
Feeling strong and life-high,
Climbing those rocks
Made her feel so alive.
But alas, gravity
On the edge, waiting
To pounce, take its chance,
Break another bone at last.
And finally the falls
Were just too much to take
She’d fallen again,
And gained fear of pain.
Life went forward, flightless,
her feet on the ground
Planted firmly,
No flying or climbing allowed.
She stopped taking risks
And she kept herself small
“Don’t even try it —
Don’t fly, or you’ll fall.”
Then one day in a dream,
She saw an old tree,
That her 6-year-old self
Dared climb up, dangerously.
She hadn’t a fear
in the world on that day;
Just strength and belief
And a need to feel free.
That 6-year-old dream girl
Would go on to be
A leaping high-flyer,
With endless brave dreams.
As the vision continued,
The perspective shifting,
It was my wishes abandoned;
The faller was me.
Face-to-face in a mirror,
The reflection was she, but
That mirror girl was more –
What I’d wanted to be.
My dream self was strong,
And was not so afraid.
But her mom hadn’t died,
Hadn’t left her that day.
With envy I said,
“But she taught you to fly!
I’d have been just like you
if she were alive.”
She looked at me squarely,
And she did reply:
“She let you grow free
And you DID learn to fly.
You learned same as I,
But you kept it inside,
When you fell, you stayed down,
Too many times.
I’m sorry you lost her
Gone before her time,
Before she could teach you
That falling’s just life,
And you’ll be alright
Just get back up next time.
You can’t let your pain
Keep you on the ground
Instead, let it fuel you,
And turn it around.
You won’t truly fly free
If you don’t know the fall.
But flying and trying are
Worth it, after all.
If you don’t take the leap,
Then you’ll never take flight,
If you don’t take a risk,
Then you’ll never live life.”
When I woke with a start,
The dream fading fast,
I couldn’t remember it,
Hold it or grasp.
But something had shifted
During that vision;
couldn’t place it, or name it,
But something was different.
I woke feeling braver.
It would all be alright.
I felt lighter and safer.
With a thought in my mind:
In flight and in life,
I’ll fall down sometimes,
But it’s time now to try
To relearn how to fly.
Next, maybe we can discuss some of your foundational philosophies and views? Is the public version of you the real you?
That’s the goal! I’m not totally natural on camera yet, so my social media presence might not feel 100% the same as the in-person version of me does, but I hope that continues improving over time.
I read a book on sobriety once (called We Are the Luckiest by Laura McKowen) where she said that a huge realization for her in getting sober was that she wanted to be one version of herself in all contexts. Complete honesty, always. It really resonated with me, and I know it’s how I want to live my life. It would be immensely peaceful, I think, to know you just have to be yourself. No matter the context or setting.
Okay, so let’s keep going with one more question that means a lot to us: If you retired tomorrow, what would your customers miss most?
I think it would be our relationship. The friendship and mutual concern that underlies the transactional reality of them being my clients. When I left my prior firm, that was what caused people to seek me out, primarily. I believe I do good work, and provide a good service, but anyone can do those things. Not everyone is going to connect with them as an friend, to put their individuality at the center of the entire financial planning process.
Contact Info:
- Website: https://www.money-illustrated.com/
- Instagram: https://www.instagram.com/money_illustrated/
- Linkedin: https://www.linkedin.com/in/jenniferswindler/
- Facebook: https://www.facebook.com/money.illustrated.advisory



