Jake Murphy, FSCP - Financial Planner

$75,000 in savings.
A $750 auto deductible.
A $1,000 homeowners deductible.

Wanting to find more cash flow to save for an early retirement.

Picture a mid-career couple with a ~$700,000 home who wants to put more toward retirement and create the option to stop working earlier. Their cash flow is already pretty efficient, so we start looking in places people don’t usually associate with retirement planning. Insurance is one of them.

Auto insurance shifts from a $750 deductible to a $2,000 one.

Potential savings: ~$780/year

Homeowners insurance goes from a $1,000 deductible to $2,500.

Potential savings: ~$245/year

Combined, that's roughly $1,000/year back into their cash flow.

What changes is that they agree to take on an additional $1,250 if there’s an auto claim and $1,500 if there’s a home claim. With $75,000 already sitting in cash, those are risks they're financially capable of absorbing.

Their deductibles simply hadn’t caught up with their balance sheet.

Now that ~$1,000/year can be redirected toward the retirement goal they actually care about.

My first 4 months in this business, I made $0.

Literally nothing.

I had no finance degree, no experience in the industry and very little reason to feel like I belonged there. I felt like a fraud.

The playbook I was given was simple: write down 200 friends and family members and start calling them to set meetings.

They even gave me the scripts.

I still couldn’t do it.

Calling the buddy I talked fantasy football with yesterday and suddenly trying to have a financial conversation felt weird. So did calling a college friend I hadn’t spoken to in 3 years.

Or my aunt who had just asked me at Thanksgiving how the new job was going while I conveniently said nothing about meeting with her.

So I chose cold calling instead.

I figured I’d rather hear “no” from someone I’d never have to talk to again.

And I heard it. A lot.

Then about four months in, one of my friend’s dads happened to be talking to him about his finances.

My friend told him “You should talk to Jake. He just started doing this.”

He became the first person to trust me.

Fast forward a few years and now people I’ve never met reach out after reading my posts for months.

That still feels pretty crazy.

Careers can look obvious in hindsight.

Mine definitely didn’t during those first four months.

Apparently a family of four in Pennsylvania now needs $247,936/year to live “comfortably.”

New Jersey: $295,110.

Massachusetts: $329,555.

The map is based on the 50/30/20 rule:
50% needs
30% wants
20% saving

That sounds neat until you apply it to an actual household.

Take a family making $250,000 with two kids in daycare, a $4,500 mortgage and student loans.

Compare them with another family making the same $250,000 with no childcare costs, a paid-off car and a housing payment half the size.

Same income, completely different definition of “comfortable.”

And once income gets higher, rigid percentage rules get even less relevant.

Someone making $250,000 doesn’t automatically need to spend $75,000/year on “wants” just because a formula says 30%.

Your income matters.

But the life that income has to support matters a lot more.

A nurse practitioner earned an extra $1,400 nearly every weekend.

She hadn’t made a single quarterly tax payment on it all year.

Since February, she had been working 16 weekend hours at an inpatient rehabilitation facility on top of her full-time job.

Most of the additional 1099 income went toward eliminating her student loans.

She had also saved 30% for taxes.

Whether that was enough depended on numbers she had never calculated.

Her W-2 withholding.

How much of her Social Security wage base had already been filled.

Her eligible business deductions.

And where the additional income placed the household within its tax bracket.

Her accountant hadn’t followed up, and she was already preparing to redirect the money from her student loans into retirement accounts.

Before investing it, we needed to determine how much of that money was actually available and whether future taxes should be covered through quarterly payments or additional W-2 withholding.

She paid off the student loans.

The next $1,400 weekend finally had a plan.

A locum PA was receiving roughly $3,800 per month in tax-free housing stipends.

Her tax-home arrangement barely existed on paper.

She paid her mother $400 each month to maintain a room at the family home while working contracts in other states.

But there was no written lease, there was no clean record showing who received the money and she wasn’t tracking her assignments or trips home consistently

If the arrangement were ever questioned, explaining it would be easy.

Proving it would be much harder.

So before directing more money toward her student loans or investments, we focused on the documentation:

A written lease.

Electronic payments into an account owned by her mother.

Records of her contract dates and temporary assignments.

Receipts showing she was maintaining expenses in two places.

And a CPA reviewing whether the full arrangement supported the tax treatment.

Paying $400 a month toward a permanent home doesn’t automatically establish a tax home. The full facts still matter, including where you regularly work, whether the assignment is temporary and whether you are duplicating living expenses.

For this PA, more than $45,000 of annual stipends depended on getting those details right.

A valuable tax strategy becomes a lot less valuable when you can’t document why you qualified for it.

A $12,000 bonus can disappear in 30 days while the 401(k) keeps growing.

That's the problem an investment statement will never show you.

Investment management is usually the simplest part of financial planning.

Most portfolios I review have some version of the same building blocks:

- S&P 500 fund
- International fund
- Bond fund
- Maybe a target-date fund or model portfolio

The harder work is coordinating everything happening around those accounts.

A $12,000 bonus lands with no plan and gets absorbed by the last few months of spending.

Someone contributes heavily to a 401(k), but no one is looking at how it fits with their IRA, brokerage account, mortgage, college savings or future tax picture.

Extra income comes in, but every dollar is forced to make a decision after it hits the checking account.

Insurance was put in place years ago, yet the income, kids, mortgage and long-term goals have all changed.

The accounts may be growing.

But the questions keeping people up at night are much bigger:

Can we afford the bigger house without feeling stretched?

Are we saving enough for retirement while still enjoying life now?

Can I retire in my late 50s or early 60s?

Can we spend more today without putting our future at risk?

That’s where planning earns its keep.

“I feel like I have more money in my checking account than I know what to do with.”

A nurse making about $125K told me that three months after we changed how her paycheck flowed.

The weird part is that less money was actually hitting her checking account than before.

When we first met, she was contributing 10% to retirement but had less than $1,000 in savings. Every month felt the same where good income came in, bills got paid and somehow there was barely anything left.

So instead of sending her entire paycheck straight to checking, we put a reservoir in between.

Her paycheck hits that account first.

We calculated what she actually needs each month for fixed bills, variable expenses, and discretionary spending.

$4900 goes to checking each month.

Everything above that stays behind automatically.

Instead of trying to save whatever happens to be left at the end of the month, she pays herself first without having to make the decision every paycheck.

Three months later, she didn't get a raise.

She just finally had control over where the money was going.

This is the kind of cash flow structure I build with clients who earn good money but still feel like every month starts over at zero.

A couple in their early 60s can have $1.5 million saved for retirement and still spend their time playing telephone between their CPA, advisor and attorney.

One office knows one piece.

You’re still the one carrying information to the next.

Picture a couple in their early 60s, retirement a few years away, with most of their savings sitting in pre-tax retirement accounts.

Their investment professional suggests a $100,000 Roth conversion.

Their CPA can tell them what tax that creates this year.

But who is looking at what that extra income could do to future Medicare premiums?

Or whether the conversion still makes sense alongside Social Security, pension income and future withdrawals?

Then the estate attorney updates the trust.

Who checks whether the IRA beneficiaries and life insurance still line up with the new plan?

That’s where people accidentally become the project manager of their own financial life.

Retirement already comes with enough decisions.

It shouldn’t become a new part-time job coordinating the people you hired to help.

I won New Advisor of the Year and hit Executive Council three years in a row.

But the moment that changed how I wanted to work happened at a nurse and mechanic’s kitchen table.

They didn’t have a big portfolio for me to manage or need a product from me. They needed help getting control of cash flow, saving more for retirement and seeing whether an earlier one was actually possible.

As I walked them through the plan, the husband looked at his wife and said he could literally see the stress leaving her face.

I remember thinking:
This is what I want to do.

This month marks 5 years in the industry, and I just took headshot #3.

Headshot #1: summer 2021. No clue what I was getting into.

By #2, I’d won the awards, doubled my income and gotten pretty good at selling — but I was still saying yes to almost anyone and needed a product or assets to make most relationships work.

Headshot #3 looks different.

Today I can work with a clinician or practice owner who needs planning around cash flow, taxes, retirement or major life decisions even if there isn’t a product to sell or a portfolio to manage.

I get paid for the advice itself.

That kitchen table meeting showed me the kind of advisor I wanted to become.

The guy in headshot #1 would probably be shocked I’m still here.

Even more shocked by what the career ended up becoming.

A 3% mortgage is a terrible debt to pay off early.

Until being debt-free is what lets you sleep at night.

Picture someone at 60 with:

$1.3M invested
A ~$2,100 monthly mortgage
A 3% rate
Retirement a couple years away

On paper, I can make a strong case for keeping the mortgage and leaving the extra money invested.

Then they tell me:

“I just really want the house paid off before I retire.”

Now we’re talking about roughly $25,000 a year of mortgage payments they no longer need to account for once it’s gone.

Maybe the portfolio ends up a little smaller than the spreadsheet says is optimal. But they enter retirement knowing one of their biggest monthly obligations is gone.

The spreadsheet may prefer the mortgage.

They may prefer the freedom.