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How to Retire in the Next 12 Months

There’s a quote about retirement, that goes something like…

Why not create a life that you don’t have to escape from.      

–Seth Godin

That sums up how I want everyone to be living.

Just create your dream life and live it right now no matter your age, gender, or wherever you are in the world.

The word “retired” reads like retired.

I want to be re – AWAKENED.

That’s what I really want to call my whole career.

Maybe you’ve heard about the FIRE movement:


All these different people penny-pinch for a while so they can retire early and then live their dream lives. Personally though, I think retirement is really boring. Wouldn’t you want to actually live your dream life now??

In this post, I’m gonna break down really interesting stories of people who’ve retired early, plus a lot of tactics you can use to retire in the next 12 – 24 months, not 10 years.

Let’s go!

How to Retire Early

So I think when people are trying to retire earlier, they think it’s conditional.

They plan to do all their work, keep their cost of living low, and THEN enjoy life later.

And I think delayed gratification is a great thing. I’m all about that. But I actually don’t think you have to wait.

A lot of people think retiring early means doing a bunch of crap now so hopefully they can enjoy it later… But why don’t you do all this crap that you like NOW — AND enjoy your life later?

I think that’s actually possible. You can have both.

Right now, I’m giving you permission to know that you can actually have BOTH right now.

So if you’re stuck in a day job you don’t like, or if you don’t even have a day job — how do you start working (even for free to start!) or start planting seeds in your life of doing the things you really enjoy? Maybe it’s cooking, writing, content creating, or maybe it’s even creating software that you promote on the AppSumo Marketplace.

If I would have stayed at Intel, my salary when I started was $55,000 a year, but if I would have worked there for the past 15 years, I may have actually become a millionaire. And then I could retire in the next 10 years and start finally living my life. I would have had 2-week vacations and it would have been okay…

But I don’t know if I would have really been fulfilled with life.

Instead, I risked it and I started a bunch of startups and tried a bunch of things out and I ended up making A LOT more than I did at Intel. And I also enjoyed the journey along the way!

Now the question is, you can have either one: The blue pill or the red pill — or whatever you want to call it — and that’s just really a decision you have to make today.

And it doesn’t have to be a big decision! It could be small decisions that you’re committing to. Every morning you wake up and you put one thing on YouTube. Or every morning you get up, and you write a little code. Or every morning you get up and you hit up one customer and say…

Hey, I want to do consulting for your marketing.
I want to do consulting for your social media.
I want to do consulting for your sales.

Whatever it is, just start planting that seed. Just once a day! Or even just once a week and guess what? Yes, your garden will be ready to eat in a few years.

BONUS: Learn How To Start A Business While Working A 9 to 5

How My Buddy Adam Gilbert Retired Early

So one of my best friends, Adam Gilbert, runs MyBodyTutor.

Now this guy had a Deloitte consulting job. So he would go in his professional suit to an office to calculate different stuff as an accountant or whatever — and he hated his life. Probably just like a lot of people out there who don’t have a job or who have a job but it’s soul-sucking.

He’s always been really into health and fitness, so he started helping people with fitness. And now for literally the last 13 years, every single week, he’s been coaching people on their health journeys — including me!

And now, Adam is more excited about life than he’s ever been before and wants to be a health coach for as long as he’s alive

So how did Adam get started?

He hated his day job, so he started advising some of his coworkers and friends for free, and he also started running Facebook ads right when Facebook started in like 2006, so it was really cheap at the time. And he was able to get some clients that way.

He started building up his clientele over time, and eventually was able to make enough money to live in New York, quit his job, and be a full-time health coach which he’s now super successful with.

#1 Tip for Early Retirement: Keep Your Cost of Living LOW

So the first thing you have to do RIGHT NOW (I did this for 10 years, actually to the point of holding myself back as I got into my thirties) is keep your cost of living low.

Straight up.

So whatever you can do to cancel your subscriptions — share Amazon Prime accounts (shoutout to JR who shares mine with me), share your Netflix account (shout out to my whole family who is on my account) — I lived on couches for a year, I lived in my mom’s house for two years, I lived in my aunt’s basement for a year.

There are ways of keeping your costs really low and what that enables you to do is you save a lot of money, but also you can then explore your career much more freely to find the things you actually truly enjoy without feeling the dependency of having to pay rent.

Give yourself a buffer by reducing your stress.

And guess what? When you find your career or things you really enjoy, you end up making a lot more money than the safe, traditional route that a lot of other people tell us we should be doing.

How else can you do this?

First, I think it’s good to get some momentum by just getting started.

Start selling some of your items, or just do whatever it takes to get money.

Drive Uber. Start a side hustle. Ask your friends if there’s anything you can do around their house that they’ll pay you for.

Just to get some things rolling so you start feeling good about yourself and gives you oxygen to start exploring what other careers you want to spend your time on.

How My Buddy Tynan Retired Early

Another example is my buddy Tynan.

Tynan’s been retired basically since he came out of the womb.

What I admire about Tynan is he has books on traveling, he does coaching, he does events, he’s got a lot of side projects, and he builds things that he’s really excited about.

There are two specific things that I think we can all learn from him:

  • He’s kept his costs really low so he wasn’t ever at the mercy of needing to have a job or do anything he didn’t really want to do
  • He shows by example that it’s a lot cheaper to live a really amazing life than all of us think

He owns an island (yeah) off the east coast, he owns a place in Japan, he owns a place in Hawaii, he owns a place in Vegas, and some other places — and you’re probably thinking that must be really expensive.

But actually, he got a lot of friends (including myself) to chip in, so we all can actually share these places.

He also bought a Bentley — and you’re probably thinking but Bentleys are like $100,000!!

He actually found one that was a few years old and got it for $20,000.

The point I’m trying to make here is that you can live an amazing life without having to have a ton of money or forcing yourself to do a bunch of work that you don’t even really enjoy.

How I “Retired” Early

So I’ve been semi-retired for more or less the past five years.

It’s not that I’m like this crazy rich person that has all this stuff — I just kept my cost of living low and I’ve saved really aggressively.

But I think what’s actually really fascinating about being retired is people think if they had all this money they finally go do a bunch of cool stuff. I went and lived in Malibu, I lived in Spain, I traveled to Tokyo. I got to do a bunch of really amazing life experiences.

I also created a podcast, we started this YouTube channel. I created other products like SendFox and KingSumo. I also got to be an advisor to AppSumo.

But I’ve got to be honest with you all…

Being retired wasn’t that satisfying.

It wasn’t really that fulfilling.

I enjoyed it and I had a good time, but it’s kind of fleeting. And I kept thinking to myself, what am I really doing here?

So through this experience, I’ve learned that a lot of the meaning we get from life comes down to you.

What matters to you? Go do that NOW.

In the last 3 – 4 months of my life, even though I consider myself retired (or reawakened), I’ve chosen to go back and be involved in the day-to-day of AppSumo.

And it’s been the most fulfilling work of my life.

But it’s also been the most challenging work I’ve done in the last 10 or 15 years.

It’s the same as playing poker with money vs. poker without money. There’s steaks on the table. This game matters a lot. There’s a lot more to gain. But there’s a lot more to lose. And with retired life, there’s really nothing to gain or lose.

So I’ve noticed that working and having people around and having things matter may be challenging to me, but it has also been really, really rewarding.

What Does Your Retirement Plan Look Like?

I’m curious, what does retirement look like for you? Let me know in the comments.

What does your retired dream life look like?

It’s not something that’s going to happen in the next 20 years. Let’s actually make it happen in the next 12-24 months.

There’s three types of people in this world:

  • People who make it happen
  • People who watch people who make it happen
  • People who wonder what happened

You have to make this choice for your own life. No one’s going to go make it for you.

I notice for myself sometimes that I’m waiting.

I’m waiting for someone to give me permission. I’m waiting for something to get fixed. But the reality is that it’s up to you to start making changes and start making things happen.

How to Create Your Retirement Dream Life

So how do we actually start crafting our lives so we don’t have to wait 10 or 20 years like our parents’ generation did and really be able to retire or reawaken and start living that perfect life right now?

Some questions to start thinking about around what your dream life actually looks like so you can start living it right now:

Where do you want to be in the world?

Do you actually like where you’re living?

I know for me, I was living in San Francisco and I was tired of all these nerds in hoodies and Patagonia being like How many employees do you have? What’s your funding? How are you changing the world? I’m like yo dude, I just want to get a taco.

And so I knew for me, I was tired of San Francisco and so Austin, Texas was the place that I felt really at home and relaxed and excited to be living.

So where is that for you in the world?

Who do you want to be around?

What’s the community that you want to actually start building?

Is it going to be in Austin, Texas? Is there an online community? Maybe if you’re in Europe or somewhere more remote, is there a place where you actually can feel good about who you have around you?

You’d rather be with first-rate friends in a second-rate city than with second-rate friends in a first-rate city any day of the week.

Think about that.

First-rate friends, second-rate city.

So think about where’s the community around you that really helps you thrive.

In your free time, what are you doing when no one’s looking?

So, for example, for my buddy JR, I organized one of his baby-daddy showers and I put on a great event because I was just really excited to honor him in that moment.

Now, think about it for yourself: What are you doing for free in your free time? Maybe you’re baking, maybe you’re playing music, maybe you’re learning to surf.

The things that you’re doing in your free time that no one is forcing you to do — is there some way to make money from that experience?

Guess what — you probably can!

Hard work = satisfaction

Do you want to work on something meaningful or do you want to just coast through life?

I think there are things that we do that feel good, but I think it’s the hard work that feels great.

A question you can really think about here is, what are you the most proud of?

For myself, what I’m the most proud of has been the hardest work.

So for AppSumo, it’s been the hardest work I’ve done in a very long time, but it’s also been the most rewarding and I’m experiencing the most growth now.

The Argument Against Retirement

I want to give you a counterexample to this whole early retirement thing.

I have a friend who works at a corporate company — I’m sure you guys have all purchased something from this company — and he makes half a million dollars a year.

What’s fascinating about him is that I think he likes his job. I don’t know if he loves it, but he’s definitely learning and growing there. But what’s fascinating about him is that it gives him the flexibility so that he can do content creation on the side. And he can be a good father and a good husband on the side.

And it gives him a good balance of whatever that life is that he is actually looking for, even though he’s not retired.

Create Your Own Retirement Playbook

The one thing I hope you take away from this video is that there’s no right or wrong way to do life. It’s about figuring out what you really WANT to do in life and what things will help you actually live your dream life.

It doesn’t have to be about sucking it up now, so one day you can hopefully retire and live a little.

Spend some time trying different things out. Study successful people’s playbooks (like mine that I’ve shared with you here, but find some other ones too) and try them out to see how they feel to you. Maybe you try mine and you don’t like it. Maybe you try being a corporate lawyer and that’s not for you either — but maybe it works for someone else.

Focus on Lifestyle Rather Than $$$

The thing that’s really important to keep in mind is that a lot of people who want to retire early, also want to be millionaires.

We’re on this planet with our paper money and digital money and this whole “million” thing became really cool.

And it is kinda cool. When I became a millionaire, it felt nice.

But there was no celebration. There were no stickers. My dad didn’t give me a badge or anything.

What I think is more interesting is actually living the lifestyle you want to live and figuring out how much money that takes. And like with Tynan, it could be a lot more affordable than you think.

What you need to live your dream life is almost never a million dollars.

It’s almost always less.

One of the books that I love about this concept is Die With Zero by Bill Perkins. If you have any money left over when you die, you wasted time working that you probably could have been doing something else.

If it’s $1 million dollars for you or even more than that, that’s great! There’s no right or wrong answer. But I think the point I really want you to take home is how much do you actually need to live your dream life?

If you want a house, a few kids, a car, a couple vacations — actually calculate that number and think about how much it is, or how much you need to be making yearly for that to happen and you’ll probably realize that it’s a lot less than you thought.

And then, think about what kind of work you’re excited about doing to make that money and you’ll be living your dream life now vs. later.

Make your own choices. That’s how you’re gonna be able to live your dream life, whether you retire early or not.


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One response to “How to Retire in the Next 12 Months”

Thread Stories Buy Edition Juttis, Kolhapuris.
March 29, 2022 at 4:04 am

It’s nearly impossible to find educated people about this subject, but you seem like you know what you’re talking about!

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