My journey to financial freedom in 2019

Finn Shewell
7 min readMar 7, 2021


NB: This post was written in early 2020/late 2019. Re-hosting on Medium now in 2021, but keep in mind some of this is dated.

Caveat: If you want a TL;DR / an update on the system I’m using now after a year of testing different systems, click here.
If you’re more of a journey than a destination kind of person, keep reading…

Financial freedom is a difficult concept to hone in on — everyone has their own definition, and most people don’t really know what financial freedom means for them. At the start of this year, I was in that camp. So I put some time aside to think — what does freedom mean to me?

Here’s what I came up with.
I want to be able to retire on a perpetuity while being able to invest heavily in the growth of anything I care about along the way. This is about as lofty a goal as I can come up with — but I feel like it’s also the conclusion most people would end on if they put in the time to think about it too.

To retire on a perpetuity means living on only the annual interest of a given set of investments each year. For example, if I want to live comfortably I’ll need around $1,000,000 at 7% annual return, giving me $70,000 each year to spend how I see fit.

Then there’s investing in the growth of what I care about. I want to be able to contribute to the success of start-ups I believe in — both financially and through the mentoring & guidance. I want to be able to invest heavily in my own self-improvement both physically, mentally, and spiritually. I want to be able to support any loved ones that need support.

In short — I want a lot of money squirrelled away for a lot of different reasons. I’m keen to write more on all of this, but for now — I’m going to share my progress towards the general goal of ‘a lot of money’ in 2019.

To get to that vague and elusive end goal, I set myself the goal of saving $10,000 before 2020.
Here’s how that went.

Not great, right?

This graph is a hot mess — but when I created the framework for it last December, I pictured it as the perfect incentive-based way to visualise my financial growth.

Here’s what I thought it would look like:

The idea was to measure my daily account balance every day, and aim to have no overlap month on month — therefore guaranteeing consistent and effective growth in savings. Here’s why that didn’t work:

  1. Inconsistent income
    This year has been fairly up and down for my income — I’ve been paid at different intervals and in various amounts each time. I’ve also transferred funds out of savings, which is where point 3) comes into play.
  2. Inconsistent expenses
    I really should have seen this one coming — obviously you’re not going to spend the same amount every 15th of the month. If I ever spent more on a given day than I had saved in the lead up to the month, I would dip below my goal threshold.
  3. Multiple accounts
    This came down to an error in the input design more than anything — because of the way I had designed my system, it became prohibitive to track multiple accounts — Which meant that I was blind to my savings and investment accounts, which meant that I was literally not even recording what I’d set out to in the first place.
  4. Human error
    My system assumed the perfect user — and that I was not. I skipped entire months worth of tracking — then spent hours working on back-logging my expenses and income, which led to reconciliation errors — it all cascaded pretty quickly.

So that’s where I went wrong. Here’s what I got (more or less) right:

  1. Simplicity of input
    Due to some very painful and lengthy formula wizardry, I managed to get macro and micro views on my spending and balances using just one data set that I transformed a bunch of different ways. All the user needed to put in was date, amount, and category of transaction — everything else flowed on from there.
  2. Focusing on big AND small picture
    When visualising finances, it’s important to be able to see the most zoomed out view possible — in this case, my daily balance for the entire year, segmented by month. But it’s just as critical to be able to zoom in to exactly what creates these daily balances — sorting transactions by category, and tracking spend in each of these. Simplicity and power is the name of the game.
  3. Incentivising growth
    Not everyone needs this — but the way my brain works, I need strong incentives to retain my money. For me, money is a token that gets something else — it’s the journey, not the destination. That makes it really hard to save — so this system created a clear and trackable incentive to lower my spending, and/or increase my income.
  4. Looking for repetitive patterns
    Outside of looking to have more money on any given day of the month than I did in the previous month, I wanted to be able to visualise any recurring patterns that occurred in either my income or expenses — and through that identify when in any given month I had the most assets, and when I had the least — so I could lower the volatility of my cashflow. I think this is generally good practice.

If you’re interested in the nitty gritty of this sheet, you can explore the whole thing for free here — including the back-end.

On balance though, this system wasn’t working. So I dropped it, and started looking for alternatives that had already been set up. As much as I love home-brew personal finance solutions, I love having a solution that works more.

So I tried a few things — I tried Ramit Sethi’s Sub-savings systems for better clarity on savings goals (see also his guest blog on — The Psychology of automation: building a bullet-proof financial system), Budget Baker’s Wallet app for one of the few bank-feed linking solutions available in NZ, and finally You Need a Budget’s YNAB system. Here’s my thoughts on each:

Sub-Savings Accounts:

Ramit Sethi is the kind of guy who’s stuff sounds like a scam (I mean his website is ‘I will teach you to be rich’ — if that doesn’t ring alarm bells in your head, nothing will) — but more often than not, his advice contains actionable, valuable intel.
I tried using his sub-savings accounts system to automate my finances, among other recommendations of his. It didn’t stick. It might for you, but for me I was caught out by the immediacy of access to each account, and the lack of specificity for general account cash allocation.

Wallet by Budget Bakers:

From there, I wanted a way to get strong insights with minimal effort — Wallet by Budget Bakers provided just that — the theory was I could set up a live bank feed that would take out all the work of importing my expenses. The reality was this feed often broke, leading to manual imports and more work than I’d signed up for. The automatic expense allocation was often glitchy too, leading to flawed insights.


I’ve known about YNAB for a while — and from the raving reviews it gets, it seemed a bit culty for my tastes. I was also a bit put off by how drastically different it is — it’s a zero-based budgeting system, which means you only budget the cash you have on hand. This intentional blindness to future income made me reluctant to take the plunge, because it wasn’t how I’d approached budgeting before. But I was more or less out of options, and they had a 34-day free trial, so I had nothing to lose.

It’s the system I’ve been using for almost 3 months now — and I know it sounds salesy, but I’ve genuinely saved almost $2,000.
To be fully transparent, that’s around 15–20% of my income — previously I’d been saving 5–10%.

It takes a while to get used to, but the principles the system encourages you to use — ‘giving every dollar a job’, for example, really work for me. Knowing exactly what funds are allocated to, and knowing that I’m only working with cash I have, has helped me a lot with self-controlling my spending. I can also set goals for my savings, track my kiwisaver and Sharesies accounts, and get reports on my spending, net worth, and a basic P & L sheet for each month.

Where I’m at now:

This year, I’ve used a bunch of budgeting systems (home-brewed, Wallet, sub-savings, YNAB) and a wealth of investment platforms (ASB Securities, Hatch, Sharesies).

What I’m ending 2019 on is a balance of the following:

I’m exclusively using YNAB for budgeting — I have granular control over my finances, I can track savings, and I can never break this budget — it bends alongside my spending.

Saving & Investing:
I’m putting about $50/month into an emergency account, and ~$200/month into Sharesies — which I’m Barbelling to about 80% medium-high risk, and 20% incredibly conservative.

At 22 years old, I’ve now made my financial systems about as efficient as they can be given my level of income. It’s made me realise one key insight — something that will guide me on my journey to financial freedom in 2020.
You can cut costs all you like, but if you’re making $50k a year, the most you can possibly cut is $50k. To really save effectively, you need to focus more on income generation that lowering your expenses. So that’s the plan for 2020 — more to follow once I actually know what that looks like.

This post is in no way intended to serve an advisory role, or be interpreted as financial advice — it is solely a record of my own experiences as I attempt to reach my financial goals.



Finn Shewell

👨‍👩‍👦‍👦 I help people work together