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FROM DEBT TO COASTFIRE: My 15 year journey to Financial Freedom

In 2009, I was in deep.

The markets had crashed, the world felt upside‑down, and I was relying on my “year‑end bonus” at Morgan Stanley to cover some big bills. Then, plot twist - due to the banks imploding, the company froze all salaries and bonuses.

Cue me feeling like Clark Griswold in Christmas Vacation getting the “Jelly of the Month Club” instead of his big check.

Clark Griswold in Christmas Vacation looking shocked after receiving a disappointing holiday bonus.
Me, circa 2009

It wasn’t just a big setback. It was a wake‑up call.


The Mess I Was In


  • Credit card was debt piling up to an amount that was 50% of my annual salary

  • College loans at ~6% interest

  • No emergency fund

  • And a VERY expensive NYC lifestyle


I knew I needed a plan.


Here’s Exactly What I Did

1. Faced my numbers

I sat down and figured out every single expense - both fixed (rent, loans, bills) and variable (food, going out, travel). It wasn’t fun, but it was freeing to finally know my numbers. (PS - this is way easier to do these days, with my favorite app - Monarch Money)

2. Built a budget that didn’t make me miserable

I gave myself room for the things that mattered- like dinners with friends - but cut ruthlessly on the stuff I didn’t care about.

3. Went old‑school with cash

I withdrew $140 every week. That was my total spending money. No swiping, just cash until it was gone. I played a fun game I called “Fake Shopping”, where I would fill my online cart with stuff, and then “X” out .... it was almost as gratifying as actually shopping!

4. Played the balance transfer game

I moved my debt to 0% interest cards. When the promo period ended, I moved it again. It bought me time to pay things down without interest eating me alive.

5. Used every windfall wisely

Every bonus, tax refund, or extra paycheck went straight to high‑interest debt and my student loans. I still put a little into my 401(k) - even then, I knew I didn’t want to stop investing entirely.

6. Stuck to the $140/week budget for years

For six years. Even as my income doubled and then tripled, I resisted “lifestyle creep.”

7. Got serious about retirement

Once the debt was gone, I maxed my 401(k) every year. Then I learned about the backdoor Roth IRA and added that too.

8. Learned to make my credit cards work for me

I used points for the fun stuff - like travel - so I could have experiences without touching my cash flow. (It took me a decade to really master this, but once I did… game changer.)

9. Invested beyond retirement accounts

When my retirement contributions were maxed, I started putting extra money into a taxable brokerage account starting with  individual stocks I believed in, but eventually moving to ETFs. 


The Mindset That Made It Work

  • I stayed patient. Paying off debt took years, not months.

  • I tried really hard not to compare myself to friends buying expensive clothes or upgrading cars.

  • I let myself enjoy some things so I wouldn’t burn out.

  • I remembered that small moves, repeated, add up faster than you think.


The Results

15 years later:

  • I went from a negative net worth to reaching CoastFIRE (meaning my retirement accounts will grow to cover my retirement even if I never contribute again).

  • I bought myself a three-year runway to slow down after leaving my corporate career - less income, more time with my kids, more workouts, and space to build my business. Now I’m down to the last year… and Mama’s ready to make some money.

  • I increased my net worth by 7300% 


Why I’m Sharing This

Because I wasn’t a finance newbie when this happened - I had an MBA in finance. And I still got myself into a mess.

This isn’t about being “perfect” with money. It’s about getting honest, making a plan, and sticking to it long enough to see the compounding magic happen.

If you’re in debt now, you can get out.

If you’re feeling behind, you can catch up.

And if you’ve been “good” with money but not growing it, it’s time to change that.


Want help building your own path from debt to financial freedom? Book a call to explore 1:1 Coaching, or get on the waitlist for Her Wealth Collective - a community for women ready to take control of their money.


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Hey, I'm Alana! I help women in Tech master their money, scale their success, and build financial freedom—on their terms.

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