It’s a raging bull market, and I’ll admit, I’m a little annoyed I don’t have a large paycheck anymore to take advantage of more investment opportunities. Every day, I see people with steady W-2 income are funneling thousands into stocks, real estate, and private deals. Meanwhile, I’m sitting here, asset rich but cash flow constrained.

In a previous post, we discussed how liquidity is the main difference between feeling like a poor versus a rich millionaire. For those of us who enjoy investing more than spending, not having a paycheck – especially when we’re already all-in – creates a feeling of deprivation. You want to invest, but you simply don’t have the cash flow to do so.

If you have a job, especially one that pays well, don’t take it for granted! Save and invest as much as you can while times are good. One day, the income will slow or stop, and you’ll wish you had invested more when you had the chance.

Since writing about FIRE back in 2009, I’ve always tried to share both the highs and lows of financial independence. Escaping a job you dislike to do whatever you want is amazing. But it’s not always sushi and skiing in Niseko.

Being cash-strapped during a bull market is one of the tougher realities of FIRE.

When You Don’t Have Enough Income to Invest in Opportunities

Right now, my family faces two existential challenges:

1. The potential decline of independent online media platforms due to AI disruption.
2. The risk that AI will eliminate millions of jobs—so by the time my children graduate in 2040 and 2043, there may not be enough well-paying opportunities for them to live independently.

Given these two trends, my plan is simple: invest aggressively and teach my children everything I can about life. I will create a partnership with their school teachers, instead of just outsourcing 100%of my children’s education to them.

The world is changing too quickly, and the lessons that will matter most – resilience, creativity, emotional intelligence, and financial literacy – must come from home.

Didn’t Have Enough Cash Flow To Invest More In Google

I’ve recognized Google’s dominance in the “new media” landscape for well over a decade. It’s become a near monopoly in search, and as a capitalist, I want to invest in monopolies that generate outsized profits. At the same time, I’ve seen how one algorithm change can make or break a media business overnight. Owning Google stock was my way to hedge against that risk.

I’d been steadily buying shares throughout the year but slowed down once the price hit $250 in September 2025. Valuations were starting to make me nervous. The stock eventually dipped to $239 on October 9, so I made my final purchase of the year the next day.

Even though I remained bullish, part of me wondered if the decline from $250 was the start of a deeper correction. The real reason I stopped buying, though, was simple. I was running low on cash and had taxes due by October 15. Without a big paycheck coming in anymore, I couldn’t keep adding to my position.

My duty is to pay income taxes to help fund the government services that about 40% of Americans don’t contribute to directly, since they don’t pay income taxes. Go USA!

Snapshot of my latest Google buys and dwindling cash balance before tax day Oct 15

Missed The Next Ramp Higher

Then, on October 21, something interesting happened. ChatGPT, another company I own shares in through Fundrise Venture, announced the launch of Atlas, an AI-powered web browser designed to compete directly with Google.

The news sent Google’s stock tumbling from up on the day to down sharply. I wanted to buy the dip because it felt like an overreaction, especially since reports showed Google’s search market share had actually started to rebound.

But I didn’t buy. Without steady cash flow mid-month, like most people with day jobs have, I had to wait until the end of the month for passive income from bonds, dividends, and rental properties. Then, on October 29, Google reported stellar earnings after the close, and the stock shot higher.

Ugh. For an investor, few things are more painful than having the right investment thesis but failing to execute. Yet again, a painful reminder that opportunity often favors those with steady income and ample liquidity.

Diversifying Private AI Investments

Now for the next case study on why having a nice big paycheck during a bull market is preferred.

Public market investments are my bread and butter for investing since it’s easy to do. However, I’ve been focused on building more private AI investment exposure for my children. The bull market has been kind to parents who invest, but the future is uncertain for their offspring. So I see investing for them now as a form of protection.

So far, I’ve allocated $193,100 to my children’s Fundrise venture account, with exposure to private AI companies like OpenAI, Databricks, Anduril, and Anthropic. My goal is to contribute a total of $300,000 over the next two years through dollar-cost averaging since the investment minimum is only $10.

But Fundrise, which invests in later-stage private growth companies, isn’t my only venture exposure. In fact, it’s relatively new, having only invested in its venture product since 2023.

Within the venture space, I want to diversify across the company lifecycle, from pre-seed to later stages. The earlier the investment stage, the greater the risk, but the greater the reward.

The Temptation to Keep Diversifying My Private Investments

An existing VC firm where I’m an LP is launching another fund that focuses on seed and Series A rounds. They just hired a new GP who I personally know and think he’s very smart, and I’d love to back them. But the minimum investment is $500,000, and even with a loyal LP discount, I’d still need to commit $250,000.

Then there’s a fellow school dad raising a cybersecurity fund. He sold his last startup to a major public company and now wants to invest in pre-seed and seed-stage security startups. He’s well-connected, smart, and genuinely likable. Supporting good people is always a joy. And his minimum investment is $100,000, which is much more palatable.

Still, investing in both would require at least $350,000 in commitments, money I simply don’t have unless I sell off other assets or go back to trading my time for money. Then, of course, I want to continue buying the dip in the S&P 500 and other individual tech stocks if they do sell off. If only I had a big paycheck again. I could invest in all three funds with ease.

Capital Calls and Reality Checks

Good thing capital commitments aren’t drawn right away. Typically, funds call capital over a 3–4 year period. The cybersecurity fund, for example, will call 25% upfront, then the remaining 75% over three years. That means I’d need to plan for about $35,000 a year in capital outlay.

If I were still earning multiple six figures, this wouldn’t be a big issue. My passive income already covers our basic living expenses. But as dual unemployed parents, an extra $75,000–$100,000 a year in venture commitments, if I invest in the other fund as well, is a stretch. Our passive income doesn’t have a large enough cushion.

Writing books doesn’t pay much (though it’s deeply fulfilling). I’ve intentionally limited my consulting work to just one client a month. And I really don’t want to get a job. The tradeoff is peace and flexibility, but the downside is less dry powder to invest.

So instead, I’ll need to reallocate capital, likely from expiring Treasury bills rather than selling appreciated stocks and paying capital gains tax. But doing so shifts some of my risk profile from ultra-safe to speculative, which could be dangerous if we’re entering a late-stage 1999-like market. Just look at Meta’s stock drop 14% so far after 3Q2025 results.

These late-cycle portfolio shifts toward more risk are often what lead to trouble once the next bear market hits. Then again, if we’re closer to 1994 than 1999, maybe going all-in isn’t so crazy after all.

Takeaways Of Earning And Not Earning During A Bull Market

I’ve shared two investment case studies – one public, one private – illustrating how lacking active income during a bull market can be suboptimal. Here are some takeaways for those of you fortunate enough to have well-paying jobs.

1) If you’re working, double down on saving and investing now.

These are your golden years, a rare overlap of steady income and booming markets. Don’t squander it. Every extra dollar invested during a bull run compounds faster and sets you up for when the inevitable downturn comes. The window of opportunity never stays open forever.

Automate your contributions, front-load your retirement accounts, and take advantage of employer matches while you can. One day, you’ll look back at this period as “the easy mode” of wealth building.

2) If you’re FIRE, embrace enoughness.

You won’t be able to invest in every hot opportunity, learn to be OK with it. You already have investments that are compounding in the background. The last thing you want is a liquidity crunch that forces you to sell assets or, worse, stress about money when you’re supposed to be free and relaxed.

It’s disappointing to feel left behind when markets roar and your income is little or zero. But remind yourself that you’ve already won a different game, one where freedom and autonomy matter more than W-2 earnings. Your existing investments are already doing well in a bull market.

Enoughness means knowing you can enjoy a slower morning, a late-morning tennis match, or a midday nap without needing anyone’s permission. Your wealth is no longer just financial; it’s measured in time and choice.

And if you continue having trouble embracing enoughness, then the only solution is to build up your passive income large enough to have a bigger weekly cash flow buffer.

3) Don’t chase every shiny deal because many won’t work out.

You’ll always see someone making a killing in some investment. Let them. Chasing yield or FOMO-driven investments often leads to self-inflicted pain. Keep your powder dry so that when true opportunities arise, you’ll have the confidence and cash to act calmly.

The reality is that almost every investment looks amazing in a bull market. But not every investment will work out. Early-stage venture, in particular, has a brutal mortality rate (~90%). That’s why I prefer diversifying through venture capital funds rather than individual startups.

If you want to be an angel investor, you need enough capital to spread across at least 20–50 companies, plus the stomach for many of them to fail. The minimum check sizes are usually $25,000 – $50,000, which poses another hurdle for most investors who want to build a diversified portfolio.

4) Always balance risk with mental freedom.

It’s easy to forget that peace of mind is also a return on investment. The goal isn’t to die with the biggest portfolio; it’s to live the richest life possible with the resources you have.

If your portfolio gives you anxiety, you’ve gone too far out on the risk curve. If it makes you complacent, maybe you’ve gone too far the other way. The sweet spot is where your money works hard enough for you to sleep well at night—and wake up excited for the day.

5) The irony of FIRE in a bull market.

Being FIRE in a bull market, paradoxically, you may end up taking more risk to try to keep up. Conventional wisdom says retirees should dial down risk once their paycheck stops. Yet, as you saw with my IRA financial professional review, I have 99% of my IRA in stocks. Partly, that’s because it’s money I won’t touch until I’m 60+. But the bigger reason is psychological. I don’t want to feel like I’m falling too far behind.

Since my old 401(k) no longer receives company profit sharing, I went all-in on equities after leaving work in 2012. It’s a strange irony: the less you earn, the more aggressive you might feel compelled to be, just to stay even. Be careful as the downturns will be more painful with a lack of income and a severely underperforming portfolio.

In The End, Investing is About Tradeoffs

At some point, you realize wealth isn’t about chasing every hot investment, it’s about building enough wealth where you can push money into the background so you can live your life freely. Whether you’re earning or not, the key is to align your money with your values, protect your time, and make peace with the fact that you’ll never capture every opportunity.

Freedom, after all, is the ultimate dividend.

Any other retirees or FIRE folks feel a twinge of envy watching this bull market roar without a paycheck to feed it? It’s strange to have achieved financial freedom, yet still feel a hint of FOMO when new opportunities appear. How do you manage the urge to chase, or the sense that you’re falling behind—even though, technically, you’ve already won the game?

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