Rethinking Money, Outside the Box
Rethinking Money,
Outside the Box
What We'll Cover
When most people hear the words financial planning, they picture traditional wealth management — large investment portfolios handed over to someone in a suit who charges a fee to manage them.
That perception comes with baggage. In one experience, the recommendation didn’t make sense, the fees were buried in fine print, and the entire process felt more like a transaction than advice. It was clear there was a better way. Instead of fee structures that were confusing and hard to understand, there could be a model that’s clear, transparent, and built entirely around someone’s life.
Because real financial planning isn’t about your net worth. It’s about aligning your money with your values, your goals, and the way you want to live.
Outside the Box
There’s an old nine-dots puzzle. The challenge is to draw four straight lines that connect all the dots without lifting your pencil. The catch? You can’t solve it by staying inside the square they form. You have to go outside the box.
The same is true in financial planning. The best answers often appear only when you’re willing to go beyond the obvious. Your financial planner should think the same way.
Not bound by industry scripts, outdated assumptions, or one-size-fits-all strategies. Instead, willing to redraw the lines to find the best solution for your life.
The right plan isn’t always the one that’s been done a hundred times before. Sometimes, the answer lives just beyond the edges.
More Life, More Moving Parts
Maybe you’re juggling a demanding career, a growing family, and competing priorities. Maybe you’re managing stock options, buying real estate, or thinking about starting a business. The complexity isn’t always about the size of your portfolio — it’s about the moving parts in your life that require coordination.
A good planner makes sure your “left hand” knows what your “right hand” is doing — taxes, insurance, investments, estate plans, cash flow — all working together instead of against each other.
Money decisions are rarely just math problems. They’re emotional. They’re mental. They’re often tied to identity and security.
If you’ve ever wondered:
Am I saving enough?
Can I buy a house? Should I?
Can I really afford to make this career change?
What’s the smartest way to pay off debt or fund my child’s education?
…you don’t just need numbers — you need context. A financial planner helps you see the whole picture and make confident, informed decisions.
Save Time, Skip Mistakes
Yes, you can figure a lot of this out yourself. But at what cost? Your time, your energy, and possibly expensive mistakes.
A great planner shortens your learning curve and helps you avoid wrong turns. That means less stress, fewer missed opportunities, and more time to actually enjoy the life you’re building.
In our industry, too many advisors are paid more if you invest more with them. That creates an incentive problem — one we’ve intentionally removed at OLIO by using a flat-fee model.
That means:
We don’t discriminate between clients.
You pay for the advice, not for a sales pitch.
Our focus stays on impact — helping you make the most of your money in every area of your life.
Those Big Moments
Retirement. Career changes. Selling a business. Buying a home. Caring for aging parents. These moments are high-stakes and often one-time decisions.
A financial planner acts as your thinking partner, helping you run the numbers, anticipate risks, and navigate the emotional side of change.
We don’t want to be hired just to meet expectations — we want to deliver unexpected results. That might mean:
Catching an insurance gap before it costs you.
Structuring cash flow so you can take a career break without derailing your goals.
Helping you negotiate a raise or navigate employee benefits and equity compensation.
The point is simple: real financial planning changes lives, not just account balances.
Beyond “Expected” Results
You don’t have to be wealthy to work with a financial planner. You just have to care about aligning your money with your life — and be ready to make intentional choices about both.
Whether you’re a young professional laying a foundation, a family balancing today’s needs and tomorrow’s dreams, or an executive with complex compensation and goals, the right financial planner can help you bring all the moving pieces together into a single, clear, empowering plan.
Because at its best, financial planning isn’t about chasing more — it’s about making the most of what you already have, so you can live well, without worry.
You can’t solve a problem with the same thinking that created it.
The right financial planner helps you see beyond the obvious, connect the dots, and move forward with confidence.
Disclosures
The content on this blog is for informational and educational purposes only and should not be construed as personalized financial advice, tax advice, legal advice, an offer or solicitation to buy or sell any security, or a recommendation to pursue any specific investment strategy. The information provided is general in nature and may not be suitable for your individual circumstances.
Olio Financial Planning, LLC (“OLIO”) is a registered investment adviser with the United States Securities and Exchange Commission, domiciled in Virginia. Investment advisory services are only provided to investors who become OLIO clients under a written agreement. Past performance does not guarantee future results, and all investments involve risk, including the potential loss of principal.
Nothing contained herein should be interpreted as a guarantee of any specific outcome. Forward-looking statements or projections are based on assumptions and current market conditions, which are subject to change without notice. Actual results may differ materially.
You should consult your own financial, legal, tax, or other professional advisors before making any financial decisions. OLIO does not guarantee that the information presented is current, accurate, or complete, and assumes no responsibility for any errors or omissions.
