When Your Money Doesn't Feel Like 'You': Aligning Financial Decisions with Your True Self

The Disconnect Between Success and Satisfaction

Have you ever achieved a financial goal that looked perfect on paper but left you feeling empty? Maybe you bought the house in the "right" neighborhood, maxed out your retirement contributions, or even reached that net worth milestone you'd been chasing, yet something still felt off.

If this resonates with you, you're not alone. In my work with individuals and families, I've found that financial dissatisfaction often isn't about the numbers. It's about the disconnect between what we think we should want financially and what truly aligns with who we are.

Money as a Mirror

Your financial decisions tell a story, not just about your resources, but about your identity, your values, and how you see yourself in the world. Every purchase, investment, and financial choice is, in some way, an expression of who you are or who you think you should be.

The challenge arises when these two versions of yourself don't match.

Consider Sarah, a successful marketing executive who found herself constantly stressed about money despite earning well into six figures. She was saving aggressively, investing wisely, and checking all the "responsible" financial boxes. Yet she felt trapped by her own financial plan.

During our conversation, Sarah realized she was managing money based on who her parents thought she should be: conservative, security-focused, always prepared for the worst. But Sarah's authentic self valued experiences, creativity, and spontaneity. Her rigid financial approach was suffocating the very parts of herself that brought joy and energy to her life.

The Identity-Money Questions Worth Asking

If you've been feeling disconnected from your financial life, these questions can help you explore whether your money choices truly reflect who you are:

About Your Financial Personality:

  • When you think about your core identity, who you are at your essence, how do your financial choices reflect that?

  • What financial decision have you made recently that felt completely right and aligned with who you are?

  • Where do you feel pressure to handle money in ways that don't feel authentic to you?

About Your Values in Action:

  • If money were no object and no one else's opinion mattered, what would you do differently with your financial life?

  • Which of your financial goals excite you? Which ones feel like obligations?

  • What does financial success mean to you personally, beyond societal definitions?

About Alignment and Authenticity:

  • When you review your spending from last month, which purchases make you feel proud? Which create discomfort?

  • How has your relationship with money needed to evolve as you've grown and changed? Where might it need to evolve further?

  • What's one financial decision you could make this month that would better reflect who you truly are?

Moving from "Should" to "Authentic"

The goal isn't to abandon financial responsibility or ignore practical considerations. Instead, it's about ensuring your financial choices serve your authentic self rather than an image of who you think you should be.

Start with awareness. Notice when you feel excited about a financial decision versus when you feel obligated. Pay attention to the difference between choices that energize you and those that drain you.

Explore the "why" behind your financial goals. Are you saving for that vacation because you genuinely value travel experiences, or because successful people "should" take nice vacations? Are you investing in that particular strategy because it aligns with your risk tolerance and timeline, or because it's what you think smart investors do?

Give yourself permission to be financially authentic. This might mean adjusting goals that never felt quite right, spending money on things others don't understand but that bring you genuine joy, or structuring your financial life in ways that honor your unique personality and circumstances.

The Ongoing Journey

Aligning money with identity isn't a one-time exercise; it's an ongoing process that evolves as you do. Your authentic self at 25 may prioritize adventure and flexibility, while at 45 you might value stability and legacy-building. Both are valid, and your financial approach should evolve accordingly.

The key is staying curious about who you are and honest about what truly matters to you, then having the courage to let your financial choices reflect that authenticity.

Remember, there's no "right" way to handle money, only what's right for you. When your financial decisions align with your authentic self, you'll find that managing money becomes less about restriction and more about intentional choice. Less about keeping up with others and more about keeping up with your own evolving values and dreams.

Your money should feel like an extension of who you are, not a costume you wear to impress others. When that alignment happens, financial planning transforms from a necessary chore into a meaningful expression of your authentic life.

~Ashley Quamme, PFP Money Mindset Guru

Beyond the Will

When we help clients with estate planning, we often suggest they think beyond just wills and trusts. Your loved ones might appreciate your life advice as much as your legal documents… This past Father's Day, I decided to take my own advice. I wandered down the trail through the woods behind our house to my favorite spot by the creek, notebook in hand, and finally put down a few (hopefully useful) words of wisdom for my two young boys. Plenty of tears later, here’s what I came up with:

My Dearest Boys,

If you're reading this, first off, know that I loved you more than I could ever express... Life's journey is short, unpredictable, messy, and beautiful. Here's a handful of things I've picked up along the road:

Live fully in the present. Yesterday is gone, and tomorrow will never come. You have only so many hugs, holidays, late-night laughs, and sunsets. And you never know which will be your last, so savor each one. 

Try not to stress too much about the future. One of my favorite quotes is, "I've been through some horrible things in my life, a few of which actually happened."  

Ultimately, only kindness matters. Not only to others but to yourself. Remorse is proof that you care. Learn from your mistakes, dust yourself off, and try again. 

Surround yourselves with people who lift you up and media that inspires you. Over time, you become the sum of who you hang out with and what you read/watch. 

You only get one body, take care of it. Stay active, eat right, sleep more, and stress less. It makes all the difference in the world. 

Helping others is the greatest shortcut to happiness. 

Money in and of itself is a horrible goal. The greatest thing money can buy is control over your own time. It gives you choices and frees you from living according to someone else's priorities. And if money is freedom, debt is a prison… avoid it like the plague.

Embrace the rule of thirds: ⅓ of your life, you'll feel on top of the world, ⅓ will be a grind, ⅓ will suck. No matter how good or bad life feels at any given moment, remember: this too shall pass. 

Challenges aren't punishments, they're invitations to grow. None of the things I am proud of came easily (the two of you included!). 

Few decisions will shape your happiness, direction, and daily life more profoundly than choosing your life partner. Pick someone who brings out your best, challenges you, makes you belly laugh and stands by you when life gets tough. 

Always be honest. Integrity is one of your greatest assets. Doing what's right and telling the truth isn't always easy, but few things matter more. 

Live your life as if you're looking back from your deathbed. I'd like to think my eulogy won't highlight the cars I drove or the degrees I earned. Instead, I hope it's filled with memories… the first fish you caught, camping trips, ski days, and those family sunsets on the beach in Costa Rica.

Above all, be true to yourself, give freely, laugh hard, and love deeply. 

I may no longer be there in person, but will be forever by your side. 

You're my greatest joys. 

Always,

Dad

What real estate can teach you about stocks

If I asked you to explain to a 5th grader the basics of how people make money investing in real estate, you probably wouldn’t miss a beat: buy a house, collect rent, subtract your expenses and the rest is profit.  Have the average person try to explain how the stock market works however and the answer will likely be about as helpful as asking Kim Kardashian to give her interpretation of campaign finance reform.