Ever since we’d moved back to Upstate New York ~8 years ago, I’ve wanted to do this…but there was always an “excuse”:

• Any time I took a vacation, I wanted it to be with my partner since we both value it so highly.

• When I left my first remote job to start my own company, I had to get started right away.

• When I closed down my company and joined a startup last year, I was operating from a scarcity mindset after years without serious income.

This time, there was no good excuse, and one day while riding along the canal (we live close to a trailhead), I realized this was the perfect opportunity to make it happen.

So I gave myself permission to just go for it.

There were some “small” issues to solve first, though:

• I’d have maybe 5 days to do this, meaning I’d have to average 70+ miles per day.

• I’d never done more than 200 miles in a week, and this ride would be nearly 400.

• I’d had ankle surgery over the winter and was still working through the final recovery stages.

• I didn’t have the right bike setup.

• Oh, and I decided to start planning less than 2 weeks from when I’d have to start my ride.

Nothing was certain. But when is it?

Fortunately I work well under pressure, and a mixture of ChatGPT and Gemini really helped to make the planning (where to stay, where to eat, how to dress) a breeze. A local bike shop also came in clutch to get me set up right.

Now the hard part: actually doing it!

About a week later, I set off on a crisp August morning (mid 60s) to make it happen.

Five days, 386 miles, and over 28 hours of riding later, I completed my route, and it was as incredible as I had hoped!

Despite riding consistently for the last 15 years, I learned a lot:

• how to manage my physical efforts to avoid cramping (the bane of my existence)

• the mental slog of long days was actually much harder than the physical aspect

• having a series of really engaging podcasts is a life-saver when riding into headwinds and physical pain

• that certain sections of the Erie Canal are gorgeous

• that chamois butter would’ve been a good thing to pack…

While I don’t know if I’ll ever do this again (especially not solo), it’s one of the few times in my life where I’ve been proud of what I achieved. It was very uncertain whether I’d make it, but it was worth taking the chance.

It’s great to check an item off my bucket list after nearly a decade of excuses. Here’s to making time for the important things in life!

After a few years of figuring things out, we sat down to make a plan: CoastFIRE through real estate. Simple enough. But then life happened:

• 2020 (COVID): my whole perspective on what matters shifted.

• End of 2020 (startup acquisition): we hit our number five years early.

• 2021 (my own bet on myself): I failed financially, hard.

So here we are. Still fine, but with more work to do to reach the lifestyle-adjusted version of FIRE we actually want.

Late last year, I sat down to do some deeper-dive planning. I wanted to know: What do we really need to live on? After running the numbers, we landed on $120k per year: comfortable, not extravagant. Enough to cover life, with some buffer for travel, investing, and the inevitable surprises.

We had our annual expenses figured out, but now we needed to figure out how much we’d need invested to be able to spend it. I’ve been aware of the concept of a 4% safe withdrawal rate (SWR, though recently revised up to 5% by the creator) for some time now, so I started with that goal in mind.

But here’s where I got frustrated: most FIRE calculators ignore the future value of money. They talk about hitting $X in 10 or 20 years like today’s dollars magically stretch as much. That’s not how it works. Inflation eats at everything. So I built a spreadsheet that actually accounts for the moving pieces. And I’m sharing it with you for free.

Before you grab the spreadsheet, though, it’s definitely worthwhile to know how to use it. Here are the key pieces you’ll need to understand.

1. Know Your “If I Retired Today” Expenses

You probably have a handle on your expenses already. If not, start there. Then ask: What would change if I walked away tomorrow?

• Work costs gone (commutes, daycare, lunches out).

• Lifestyle shifts (maybe more dinners out with family, more travel).

• Debts that eventually disappear (mortgage, renovation loans, student loans).
  

We picked $120k/year because it’s above our current budget ($92k in 2025) but leaves room for growth (more travel, keep investing) and unknowns (lump-sum costs, healthcare).

2. Don’t Ignore Inflation

Over 50 years, U.S. inflation has averaged ~3.8% annually1. Sometimes lower, sometimes higher, but it compounds. So instead of assuming $120k means the same in 20 years, I modeled what that money would actually buy as time goes on.

3. Track and Model Investments Honestly

If you’re a Boglehead or otherwise have a simple asset allocation, you can lean on historical averages.

If you’re like us—a mix of real estate, stocks, and a little crypto—you need to break it out by asset class. Otherwise, you’ll be fooling yourself about how your assets might grow.

Important: Start with taking stock (no pun intended) of what you already have in each class, since this is the base you’ll build on!

4. Grok Usable vs. Non-Usable Net Worth

Your house? Not usable if you’re planning to live in it. Same for cars or land you don’t intend to sell. Count only what’s actually working toward financial independence (FI).

5. Model Your Future Contributions

Unless you’re already FI (or want to work longer than necessary [see point #8 below]), you’ll need to invest more to speed things up.

More uncertainty comes as you go farther away from today, so unless you have some very clear known windfall, focus on dialing in the near-term numbers.

Got some uncertain life events (i.e. startup acquisitions, illiquid investment returns, inheritances) coming up? Build those out as different scenarios in different spreadsheet tabs.

In 2024, we thought we could scrape together $20k in 2025, then $40k/year from 2026 on. Manageable, if a little tight, since I took a relatively low-paying job in 2024.

Then a surprise hit: I accepted a new role that nearly doubled my comp. Thanks to a solid 401k match and 15 years of living below our means, we revised our plan: $30k in 2025, then a whopping $140k2 annually from 2026 forward.

Life rarely goes to plan, but sometimes it surprises you in the best way.

6. Appreciate the Snowball (DRIP)

Some of our investments throw off dividends (about 1% annually), and yours may too. It’s not a lot at first, but each year the portfolio grows, reinvesting those dividends makes hitting annual goals easier.

Some of our other investments are more…lumpy. We’re in a local real estate syndication that averages 5% dividends, though we’ve had worse years and will (hopefully) have much better ones. Since those returns are all over the place, we assume the average and will be pleasantly surprised when (if?) it outperforms.

7. Find Your CoastFIRE and Full FIRE Dates

Once you have a model of your expected expenses (in today’s dollars), know your current investments, and have a projection of your annual investment contributions, it’s time for the fun part: figuring out when you’ll hit Escape Velocity (a.k.a. “F You Money”).

For us, the math looks like this:

• 20x $120k = $2.4M (aggressive 5% SWR)

• 25x $120k = $3M (traditional 4% SWR)

But remember, this is only our Escape Velocity if we retired at the end of 2024. Inflation’s a b****, so our expenses (using average inflation) is already up to ~$125k if we retire in 2025! It’ll just keep increasing from there, which is why I built my spreadsheet to calculate the right numbers every year.

Our usable net worth today? Between $1.2 and $1.4M (depending on how our residential real estate divestment goes). At our old contribution rate, full FIRE was somewhere between 2036 and 2041.

At our revised rate? 2031–2033.

The wildest part? Most of the heavy lifting comes from the money we already invested. The new contributions move the finish line closer by 5-8 years, but compounding is really what carries the day.

Just for grins, I decided to create one more scenario (no investment beyond 2025). Even still, our aggressive (5% SWR) date is only sometime in 2042. That means that if we want to fully retire at 53 (me) and 51 (partner), we just have to let our investments grow across the next 17 years.

8. Define What FIRE Looks Like to You

Hitting a number doesn’t automatically mean quitting. For some, it’s a chance to slow down. For others, it’s the freedom to bet on themselves in new ways.

A friend of mine is on track to be FI in Silicon Valley by 40, even with an insane Bay Area mortgage and two kids. But instead of walking away, they want to consult in their field. Recently they told me that when I founded a bootstrapped startup in 2021, they really wished they could do the same, but getting to FI was a higher priority. As one of my smartest and most driven friends, I’m excited for what’s ahead for them!

And really, that’s the allure of FIRE to me: not retiring early, but the options it unlocks.

The Goods

As I promised at the beginning, here’s the spreadsheet I created that makes it really easy to calculate this for yourself. You can grab it here for free (and if you find it helpful, I’d love it if you subscribed) and change the dummy numbers to match your situation.

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Retirement Calculator Template

67.8KB ∙ XLSX file

Download

An Excel Spreadsheet (can be imported to Google Sheets or Apple Numbers) for FIRE tracking.

Download

Your Turn

Do you know your FI number? Is it close, or does it still feel a lifetime away?

Earlier this year I decided that I wanted to move on from my current job at an early-stage cybersecurity startup. The job market is already a mess, and I really don’t fit cleanly into many job descriptions (two-time founder, quickstudy but without a deep subject matter expertise in some of the most commonly sought after areas). Translation? I sent out 50-100 applications (after scrolling through thousands), and nearly all of them ended with a short, simple denial email.

The one thing I do have going for me is a strong network of VCs, founders, and technical leaders I’ve gotten to know along the way. And as luck would have it, one of those connections was looking for someone exactly like me.

A Rollercoaster of Emotions

After five rounds of interviews, both the company and I were super excited to work together. There was an offer on the table, and all I had to do was sign.

And then–literally at the last moment–I discovered that I had a non-compete.

You might think “Wait, how did you miss something like that?!” Fair point. I actually did look at the beginning…but only at my personal email (where I received and accepted my current employer’s offer). What I didn’t realize was that non-competes don’t always come with the initial offer—sometimes they sneak in later, during onboarding. That was my situation. It was sitting quietly in my work email, and I had completely forgotten.

Had I signed with the new company and given notice, my current employer could’ve fired me on the spot. And here’s the kicker: I would’ve still been stuck honoring the non-compete (in my case, up to a full year on the sidelines).

Your Mileage May Vary

Here’s the wild part: I thought non-competes were basically over. Turns out…not so much. There is a national ban[1], but it’s tied up in court limbo and doesn’t actually apply right now.

If I lived in California (or one of the few other states where non-competes are banned), no problem. But I live in New York, where a ban was proposed in 2023—and then vetoed[2]. So here we are.

I even told a friend of mine in Silicon Valley about it, and they were shocked. They assumed non-competes were some early startup problem and were otherwise dead for years. Nope. Outside the Valley bubble, the rules are still very real.

The Letdown

Because the last thing I wanted was to leave my potential new company with a legal mess (or end up paycheck-less for an undefined amount of time), I asked them to run it by their legal team. They’re also an early-stage startup, and the thought of entangling them in a fight over me just felt wrong.

After a few days of digging, their lawyers came back with the verdict: too risky. That was that. I’d been pretty sure it was going to fall apart, but still…when I got the news, I was sick to my stomach for a couple of days. The only solace was that I caught my error before I made it worse.

Silver Linings

The twist? The founder of the company I couldn’t join ended up introducing me to my next job.

About two weeks later, they reached out and said they knew someone looking for someone like me. I looked at the job description and thought it was a stretch (I actually nearly passed on it from the start). But I figured that one conversation wouldn’t hurt.

Fast forward: six(!) rounds of interviews later, both sides realized it was a great fit. The parts that intimidated me at the beginning don’t worry me anymore. And now, I’m genuinely excited to join this team and give them everything I’ve got!

Your Turn

Have you ever run into a situation like this—a dealbreaker you didn’t see coming? Or something else that blindsided you in a job search?

The market is chaotic right now, and honestly, it feels like none of us know what’s around the corner. But if this experience taught me anything, it’s that the detours can lead somewhere better than you expected.

And for now? I’m just grateful to have a job I’m looking forward to again.

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Meanwhile, I’m switching jobs: from a very early-stage startup (low salary, high potential upside via equity) to a late-stage startup (market-rate salary and bonus, smaller potential equity upside) to better align with my career goals.

Because I like to keep life…interesting, we’re also selling our residential real estate portfolio and rolling the proceeds into one or two short-term rentals.

Fold in job market instability in tech, relatively high interest rates (for those of us who bought homes prior to 2020), and you might wonder: Why renovate now?

1. We’ve Been Putting This Off for Years because of my “Founder quest”

My partner has been incredibly patient of my need to answer “what if.” I always promised that after my quest concluded (success or failure), I would focus on making up for the years where we scrimped and scraped through. This is a big one that we kept pushing off.

2. A Renovation is Enjoyed in Real-Time

The beauty of responsible leverage (especially for homes) is that you can enjoy the upgrade now and pay for it over time.

If it takes us 10 years to pay this off, that’s 10 years of daily enjoyment–starting now. We know we’ll enjoy it because we (fortuitously) renovated our kitchen and dining room in 2019, and we appreciate those spaces every day. Without that update, I’m certain we would’ve sold our house during COVID lockdowns.

And while saving up to pay in cash is an option, it means:

• Potentially missing market returns on that cash

• Paying more later (due to rising labor and materials costs)

3. Our Downside is limited

If the market dropped 50% and I temporarily lost my job, we’d still be okay. We have:

• Emergency reserves to cover a few months without income

• The ability to cut back on discretionary expenses (about 45% of our budget)

• The option to redirect cash from selling our rentals instead of redeploying it

4. Uncertainty Isn’t Going Away

Personally speaking, I don’t see AI’s transformation of the job market slowing down any time soon. While I’m not a doomsdayer who thinks we’ll have 50% unemployment, I do believe temporary displacement will keep happening while we all figure things out. We’ve already seen companies over-index on GenAI and reverse course, and I’m certain it’s not going to be the last misstep.

Your Turn

Would you renovate right now? Or does it seem like tempting fate? Judging by the number of construction dumpsters I’ve seen in our neighborhood, I suspect we’re not the only ones making upgrades in uncertain times.

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We’ve officially burned through our annual vacation budget…5 months early.

The 20-something version of me (okay, maybe even early 30s me) would have panicked about this budgeting catastrophe. But honestly? I’m at peace with it.

Here’s why.

Making up for Missed Vacations

One thing I’ll never get more of is time.

When COVID hit, we lost our ability to travel just like everyone else. I still recall excitedly booking our European vacation in January 2020, only to cancel it two months later.

Looking back at our budgets from that time, we spent just $10,000 on travel combined across 2020 and 2021.

Celebrating Big Moments

We usually take a family-oriented trip in the Spring as our first weeklong vacation, but this year we decided to kick things off in February with a Hawaiian getaway to celebrate our 10-year wedding anniversary. We honeymooned there and always wanted to return, and this was a great excuse to do it. This time we explored new islands via cruise ship. Some days genuinely felt like we were back on our honeymoon, which is quite a magical feeling a decade into marriage.

We also had several other special occasions this year. After a 10+ year hiatus, a few of us in my family decided to plan our first annual family reunion. Despite all of us being hours apart and busy in our own day-to-day lives, we managed to bring together almost 70 people! It was such a nice feeling to talk to some family members whom I hadn’t seen in more than 20 years.

On another trip, we got to visit one of my younger siblings, meet their partner for the first time, and experience a few days in their everyday life. It was really special to us and something we hope to repeat in the future.

And next month (but already part of our 2025 spending), we’ll travel to meet up with another of our siblings for their wedding!

We’ve Learned What Matters Most

Over the years, we’ve really honed in on the few things we’re okay with spending disproportionately on. At the top of the list: travel.

For us it’s not some competition or status symbol, but rather a deep appreciation of new experiences.

You’ll often find us hiking a breathtaking trail, perusing local bookstores, sipping coffee at a local café, and tasting our way through a new city.

The Future is Always Uncertain

We’ve had friends our age who’ve lost their lives in accidents or who’ve received a diagnosis that changed everything. When those things happen, the opportunity to travel freely is too late.

And even without tragedy, we’re living in tumultuous times: AI is eating formerly safe jobs left and right. Tech layoffs and “The Great Flattening” are a part of life for many. Our purchasing power could take a dive at any moment, and I don’t know how long it would take to recover. Maybe it wouldn’t, or maybe our health would be less certain by the time it did.

A Reality Check

We wouldn’t be able to travel like this if we hadn’t spent our 20s living below our means and catching some lucky breaks with investments. I’m aware that this isn’t everyone's reality.

But that’s part of what motivates me to write — we’re all dealing with different forms of uncertainty.

And even in abundance, it’s not always clear how to use what we’ve earned or saved.

Your Turn

Are you over budget on travel this year?
If so, does it stress you out… or does it feel like a conscious choice?

There’s no right answer, just your own priorities, your own season of life, and your own way of measuring what’s worth it.

Let me know. I'd love to hear.

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Over four years ago I left my job as an individual contributor in cybersecurity to start my own company. Just a couple years earlier I’d sworn that I’d never do that because the uncertainty and stress weren’t worth it. But there I was on my last day, saying goodbye to great colleagues and “jumping out of a perfectly good airplane.”

What I didn’t–couldn’t–know was that that decision would end up costing me more than $5M.

I’d been in cybersecurity for a while by then. I started in an R&D lab before moving to the Bay Area, pulled in by the excitement of startup life and the so-called “lottery tickets” of early-stage company equity. I still remember the day my stepdad–a lifer at one company in one small town–essentially yelled at me for leaving my first job to pursue something as unknown as a startup.

But it worked out.

I joined early enough to get meaningful equity. I loved what I did and the people I worked with (it’s still the greatest group of people with whom I’ve had the pleasure of working). And eventually, the company was acquired.

At the time, I was already planning my exit. I’d made up my mind to start my own thing. The acquisition didn’t change that, partially because I had very little room to grow internally, and I wanted to see if I could actually build something on my own. I waited two quarters to vest 1/8th(!) of my new equity package, then left.

Someday I’ll write in more detail about my company-building experience (where I got it wrong, and where I got it right), but suffice it to say that I learned an unbelievable amount. The phrase “drinking from a firehose” doesn’t do it justice–I was drinking from Niagara Falls.

Many of those lessons were huge growth opportunities for me, and I honestly don’t directly regret having started my own company. One of the biggest reasons why I decided to start something was that I didn’t want to look back and say “what if?” at the end of a well-paid but otherwise unremarkable career.

I definitely achieved that.

But it came at a significant cost.

To add insult to injury, after I decided to shut down my first company due to a toxic cofounder relationship, I had a chance to go back to the acquired company. I could’ve rejoined and started vesting right where I left off.

But I said no. Why?

Because my cofounder (who was not full-time) slowed me down, causing me to take longer than I should’ve to discover that product-market fit was really not there. And around the same time, I had a motivational meeting with a founder friend of mine who went through a similar situation a few years prior, pivoted to start their company solo, and ended up building something reasonably valuable. They encouraged me not to throw in the towel just yet and to bet on myself again.

So I did. And honestly, it almost worked out.

The second company I started did have some early success and was growing. Simultaneously, I landed some critical channel partners that opened up a lot of promising opportunities. But after about 18 months of building (and a few tough breaks on deals), I decided that I couldn’t scale earnings to the level I needed. I even had a few acquisition conversations, but eventually those fizzled.

Across the two companies, I had been bootstrapping for nearly 3 years, and I wasn’t comfortable continuing to burn up our savings. So I joined a different cybersecurity company.

I gained many things, but financial success was not one of them.

They say “pics or it didn’t happen,” so here’s a (redacted) picture of my stock holdings that I gave up back when the price was less than 25% of its current value (roughly late 2021):

Everyone says that two things in life are certain: death and taxes. But I’d argue that there’s a third: uncertainty.

What looks like a great move at the time can turn out to be an expensive mistake just a few years later, just as something that feels terrible at the time can turn into a great opportunity. Hindsight is 20/20, but the future is unknown.

From personal conversations with friends, people I know through Internet forums, and many of the news stories I see every day, I’m confident that there are a lot of people in the world right now living with an incredible amount of uncertainty. It’s not just about money, though, but about relationships, identity, and even where to live.

I’m starting this blog for you.

For those asking questions like:

• “What will work look like in 5 years?”

• “Should I spend money and enjoy now or squirrel away as much as possible?”

• “Will things ever feel certain?”

My hope is that “Certainly Uncertain” becomes a place for sharing, commiserating, and finding community in our uncertainty–even if we don’t always have the answers. And while I’ll (at least at the beginning) keep my writing roughly anonymous, know that there is a real human at the other end of these posts, typing away at a keyboard about real challenges and uncertainties in their own life.

Now I have.

I’m in my mid thirties, and I’ve had a lot of experiences that have shaped my thoughts of the world. I grew up in a small town just above the poverty line, put myself through school, and figured things out by the seat of my pants. 15+ years into adulthood, I’ve realized that most of the big decisions I’ve had to make were made with a significant amount of uncertainty. Sometimes that uncertainty came from a lack of mentorship or connections. Sometimes it was self-inflicted. And sometimes it was just…life being unpredictable.

Certainly Uncertain is my space to explore that feeling: the messy, unpredictable, often uncomfortable state between knowing exactly what to do and having no clue at all. I know I’m not the only one who’s navigated life without a map, and I want this to be a place where we can share those stories, learn from each other, and feel a little less alone in the process.

If that strikes a chord, I’d love for you to subscribe and join the conversation.

The first few posts are already available:

• My $5M “Mistake”: When Betting on Yourself Doesn’t Work Out

• We spent our travel budget by July — and I Regret Nothing

• We’re Renovating in the Middle of a Shaky Economy — Here’s Why

Going forward, I’ll generally be sharing long-form content once every week (sometimes more, sometimes less). There will also be content on Instagram (@certainlyuncertainblog) and X (@Cer10lyUncer10).

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