How to Stop Planning for Retirement and Start Building Now

Show initiative, deploy capital, take calculated risks

Most people spend more time planning their retirement than building a life they don’t want to retire from.

Last week I wrote about why organizing your 20s and 30s around retirement is an admission of defeat.

You Don't Actually Want to Retire

A lot of you reached out asking: okay, but how do you actually make the shift? How do you go from counting down the years to being in a position you don’t want to escape from?

Here’s what worked for me.

Showing Initiative

I remember my parents always telling me this when I was younger. In middle school, high school, and so on. Guess it stuck with me because I am writing about it right now and I’ve shown a lot of initiative in my adult life.

Going back to my first job out of school. 22 years old. Hated it. Showed up that first day knowing I didn’t want to be there. I’d actually interned at that firm the summer before my senior year and really did not like it AT ALL.

So why did I go back full time? Well sometimes you gotta do what you gotta do. My goal senior year was to find a job I actually enjoyed more, and I got some other offers, but none of them were in New York where I wanted to be.

So I took the job at the firm I’d interned at, the one I knew I was going to hate, because it was a reputable financial services firm in Manhattan.

Dead on arrival. Showing up knowing I didn’t even want to be there.

So first day, I immediately started thinking: how do I get out of this?

I started networking heavy. I went to events even though I didn’t want to go. Networked a ton internally with other departments and even more externally.

Networking in traditional finance felt artificial, everyone had an agenda, myself included. But I did it anyway, because I knew that submitting job applications into the void wasn’t going to get me anywhere.

Also ripped the band aid off and started on the Chartered Financial Analyst (CFA) track. For those unfamiliar, considered to be THE credential on Wall Street. It’s no easy undertaking. Three parts, typically about 300 hours of studying to pass each part. Pass rate was around 40%.

I knew I needed to be proactive. Show initiative. And I knew these credentials proved many things: discipline, hard work, and motivation.

When I passed that first exam, it was like a huge weight had been lifted. All those hours paid off. That credential made me a more interesting hire. I was looking at analyst roles competing with fresh college graduates or recent graduates like myself, but this helped me differentiate a bit.

Almost 18 months after showing up dead on arrival, I ended up getting my next job through a connection. The introduction got my foot in the door with the hiring manager. I still had to go through several rounds of interviews and do a case study, but I landed it. This was at the end of 2019 working on investment research of hedge funds and private equity.

Fast forward into the next year. 2020. COVID. Lots changed. Stuck at home, started listening to more podcasts. Lots of walks. Time out of the hustle and bustle of NYC.

By mid 2021, I was ready for the next thing. The next job I got was at a startup that I heard about on a macro finance podcast Macro Voices. Heard the CEO on the podcast. Saw they were hiring a sales hire. I had a research background at that point but felt like I was more of a sales person. I reached out to the hiring manager for an interview. Crushed all the interviews including with the C Suite as I already knew the business well from my diligence ahead of time.

Got that job as the first sales hire.

Fast forward to my next job in 2023. My current employer. Reached out to one of the co-founders on Twitter, had an interview, got the job.

The main point: you need to be proactive. You need to show initiative.

This is only becoming more important. The gap between high agency/high initiative people and low has never been wider. So how do you actually show initiative?

Network constantly. Not just at formal events, but everywhere. Online, in-person, through introductions. Build relationships before you need them.

Build in public. Start sharing your thoughts, your work publicly. Twitter, LinkedIn, a newsletter, whatever. Let people see what you’re capable of before they meet you.

Get on the forefront of new technology. The people ahead on AI right now are going to win. Same was true for the internet, mobile, social media. Be early to what’s coming.

Provide value upfront. If you want to work somewhere, do some work first. Send the hiring manager a case study or do a project upfront. Show them what you could do for them before they even interview you.

Spend your free time learning skills that get you closer to where you want to be. Not just consuming content - actually building, creating, practicing.

Or spend your free time building your own company. Even if it goes nowhere, you’ll learn more in six months of building than six years of consuming.

Rethinking Retirement Savings

I was fortunate. My father taught me personal finance principles from a young age. When I started working part-time around 15 or 16, he taught me about retirement accounts, even matched my earnings for the year.

He gave me a useful foundation in traditional retirement planning and living below your means. Spend less than you earn, put the excess into the market - S&P 500.

I still keep a lot of those principles. But my thinking on long-term saving, retirement, and how to invest has evolved.

I haven’t had a 401k in almost five years. I’ve been working at smaller companies that don’t offer traditional benefits. I traded the 401k for company equity, which probably will amount to very little with my previous employer, but that’s part of the learning process.

I’ve put most of my cash flow since 2021 into Bitcoin. Most of my net worth is in Bitcoin, though I also have some equity exposure and traditional IRAs.

But most importantly, my thinking on my relationship with work and retirement has evolved. I’m not waiting 30 to 40 years to pursue what I want to do. I’m confident that if I pursue what I want today, I’ll get there when I’m ready in the future.

I want more autonomy over my time. But I’ve realized retirement isn’t the only path to that. If you get closer to work you actually want to be doing, you start getting autonomy now - not in 30 years.

Here’s how I think about capital now: I want long-term savings that compound without me touching them. But I also keep a separate buffer I’m willing to deploy - for a business venture, for runway to take a risk, for giving myself options.

When I took my current job at a startup, I walked away from traditional benefits - 401k match, health insurance, all of it. But I had savings if needed and conviction in what I was building. A big part of this for me is getting closer to what I’m being called to do. Following that, I don’t think I can lose.

You can’t bank on a pension or Social Security. So yes, save for the long term. But also keep capital available to invest in yourself - because that’s the best investment you can make.

I’d also challenge the common allocation playbook. S&P 500, maybe some bonds. For wealth building in this day and age, you need to invest on the frontier where there’s disproportionate returns, asymmetric upside.

That’s why I like Bitcoin. That’s why I think it’s interesting to invest in yourself to build skills, particularly in the AI space.

When to Take Risks and How Much Runway You Need

It’s always easier to take risks when you don’t have as much responsibility.

The first job I took away from the traditional career path - with the 401k and all that - was before I was married. Fewer responsibilities, fewer people relying on you.

So if you’re younger and thinking about it: start pursuing those interests. Start taking calculated risks. Join the perceived risky company. Make the investment in yourself.

I felt comfortable doing that when I had very little responsibilities.

But I’ve continued on this path even as I’ve grown my family, because now I have conviction. Now I’ve figured out how to make it work. I’m working at a small company, no 401k, no traditional health insurance (I figure out alternatives), saving in Bitcoin.

On paper, I’m considered very risky. But I don’t feel that way. I’m just pursuing something that’s interesting to me.

How much runway should you keep liquid before making jumps?

Generally a good practice is to have up to 6 months of expenses for an emergency. But you may want more if you’re starting a business that needs a longer runway for cash flow purposes.

It depends on what you’re building, what the initial investment is, what your financial situation looks like.

Even now, married with a child, I’m still not uncomfortable taking risk. I’m still going to pursue what I think is the path I’m meant to be on.

I’m not going to play it safe, especially because that has never been riskier.

Playing It Safe Has Never Been Riskier

The Path Forward

You don’t need to follow my exact path. But you do need to make a choice.

You can organize your life around eventual escape - save everything, defer everything, count down the years to 65. Or you can start building now. Build skills. Build capital. Build conviction. Build something you don’t actually want to retire from.

The gap between those two paths only gets wider with time.

I spent my early 20s hating my job and studying for the CFA on weekends. But every networking event, every credential, every cold email was moving me closer to work I didn’t need to escape from.

That’s the shift. Not quitting everything. Not taking reckless risks. But refusing to accept that your best option is to defer life for 30 years.

You only get one shot at this. The future is too uncertain to bet everything on a far-off finish line.

Build something you don’t need to retire from.

If this resonated with you, share it with someone in their 20s or 30s who’s already thinking about retirement instead of building. I send one of these each week, so make sure to get on the list. And if you reply or comment below with what you thought about this piece, that helps me keep improving.