Hey — scrum time!

Instead of user stories and bug fixes, we’re going to plan for your life, for the next 30-40 years…because how often do you do that?

We’ll keep it short and focused:

Yesterday: Where you’re at.

Blockers: What’s in your way.

Next Sprint: What to build next.

Today: What you can do about it starting today

Sound good? Let’s go.

Yesterday

You’re doing well.

You’ve built a solid career in one of the best industries of our time. Software engineers earn more than most fields, work with smart people, and often have the freedom to work remotely.

You’re not behind — not even close.

But here’s the thing: for all the flexibility that software engineering offers, most of us are still running a centralized system when it comes to our life architecture. One employer. One country. One source of income.

That was me, too — right up until I was a tech lead in Seattle.

On paper, I had everything dialed in: high comp, solid RSUs, side projects, and an enviable resume. But my entire livelihood still depended on one company’s payroll cycle.

If that system went down — layoffs, policy changes, industry shifts — that puts my family at huge risk.

Then the layoffs of 2023-2024 happened, with various mandatory return to office policies.

By then, I was already living my dream life — no longer a tech lead, no longer location-dependent. But I watched friends lose their identity overnight. People making $200-300K+, suddenly with nothing. These weren’t under-performers. These were engineers who scored “meets or exceeds expectations” on their performance reviews.

They were able to find replacement jobs, sure. But it likely wasn’t ideal.

That’s when it became crystal clear: even if you’re earning well and have equity, you’re still running a fragile deployment.

Blockers

Income-Freedom

You have a single point of failure. If you lose that main source of income, you are now in the big scramble to find something.

And those RSUs and stocks? They don’t pay the bills unless you sell. Equity value isn’t income until you sell.

I know engineers who were serially successful at picking pre-IPO companies and took part in going public. I also know engineers who, despite working 14-hour days every day, still haven’t seen their company go public.

To each their own. But it’s not for me.

Dividends come closer to real income, but you’ll need a massive diversified portfolio of dividend stocks — maybe dividend kings — to make that work. If you feel confident managing that, great.

The reality for most engineers? You have about two revenue sources: your income, and the bit of dividends you receive.

But here’s a question that hardly gets asked, because we’re all caught in the momentum of life:

Even if you never lose your job or are always able to find another company to work for, will you feel fulfilled if you continued coding and solving engineering problems for the next 30-40 years?

If the answer is yes, then GREAT. You’re genuinely living your dream life and don’t need to consider anything else.

If you cannot see yourself being happy coding for the next 30-40 years, then you’re simply following the momentum of life. I hope you’re not deceiving yourself that you’re happy and living a great life when that’s not entirely true.

I realized the software life isn’t for me in the long term. So I’m not going to “just roll with it” for the short term. It’s about putting in the work today so that you have the freedom to say “no” to the things you don’t want to do.

Time-Freedom

Even if you maintain your employment, your job forces you to be somewhere.

After eight years in Seattle, I needed a change. I had already built options for myself — second residencies, alternative bases, investment income streams — but a portion of my income was still location-dependent.

That was the final piece to solve.

The pandemic made this clearer. Being stuck in one location with no ability to move wasn’t great. In the beginning, I didn’t want to be traveling until more was known about how serious the illness was. But when the facts came out and I wanted options, I didn’t have another place to go that was more open.

I was technically “free” to work remotely. But I wasn’t actually free.

I opted not to go the remote engineer route. Time with family on my own terms is much more valuable at this phase of my family life, and what my children need right now.

This is the real blocker — not your technical skill, not your salary, not your ambition. Just architecture.

Next Sprint

Here’s where we shift from analysis to action.

In this next sprint, start designing your life like you’d design a scalable system.

You already think in systems — so use that same mindset for yourself. Flag Theory gives you the design principles and requirements:

Redundancy: Don’t rely on one employer, one country, or one source of income. Prevent unrecoverable failure here.

Availability: Mirror your earning potential through secondary income streams, even if they start small. Geo-replicate your assets and income streams to prevent complete data (wealth) loss, go for 4 9’s.

Modularity: Design each part of your life independently — your residency, tax residency, citizenship, wealth storage, and income streams — so a failure in one doesn’t cascade into the rest. Be fault tolerant and well encapsulated.

You don’t have to quit your job to start this.

You can build your Total Freedom roadmap while you’re still employed — just like I did when I was a tech lead.

The first step I took? Income diversification.

I focused on replacing my active income with investment income, across geographies. Not all at once. Not overnight. But deliberately, over time, building a system that could eventually run without me needing to punch in every day.

My family was highly supportive, even when my extended family was confused. Now they’re not. They know exactly why I did this. They just wish they’d started when I did.

Begin by asking:

– What would my life look like if I wasn’t required to be a software engineer?

– How could I redesign my environment so that work becomes optional, not mandatory?

– What systems could I deploy today that give me more resilience tomorrow?

Start small — a second residency, a side income stream, a distributed asset structure, or simply learning how tax residency differs from physical location.

Each of these flags gives you optionality, the same way microservices give systems resilience. If one fails, the rest stay online.

Today

You don’t need to wait for a perfect plan — you just need to deploy one small action today.

The saying is: you gotta wrap up the design phase at some point and start the MVP. Your stakeholders don’t have all day

You can have a great design. Sometimes over-engineered. Sometimes prematurely optimized. But you’ll never know until you start coding and deploy it to production.

So stop architecting in your head and ship something.

Read one article from our Total Freedom Library. Watch one video on our channel. Subscribe to the newsletter for deep dives on residency, tax strategy, and income design.

You already know how to architect systems. Now you’re just applying that same logic to your life.

So here’s your standup question for the day:

What will you focus on today?

Because freedom isn’t built in one sprint — it’s shipped, one intentional decision at a time.