What They Don’t Tell You About Retiring Early // Lessons From Jim Wang

As much as we love sharing our musings about our still-imaginary early retirement, we especially love sharing lessons from people who’ve done this crazy thing and retired early in actual, non-imaginary reality. Like our interview earlier this year with Robert and Robin Charlton, authors of our favorite early retirement book, How to Retire Early.

Today we’re thrilled to be sharing lessons from Jim Wang of WalletHacks.com. Jim retired at age 30 after selling his first massively successful first blog. But early retirement wasn’t what he expected. He’s clearly made a ton out of his years since then — including launching his current blog Wallet Hacks and other businesses — but the transition wasn’t easy or instant. He’s here today to share what they don’t tell you about retiring early.

I met Jim at FinCon, and knowing his back story, expected him to be a bit aloof, a bit unapproachable. He got paid a whole bunch of money for a website he built all by himself, you guys! But that was just me projecting — Jim is an incredibly down-to-earth, humble guy. Oh, and he’s hilarious. So I’m honored to have him guest posting here today!

Here’s Jim! 

At the age of 30, I retired.

Six years later, I run three separate businesses and love every minute of it.

Financial independence is a popular phrase lately and with good reason. No one relishes the idea of working 40+ years until “retirement,” when you can finally have some fun.

If you break from the conventional thinking, there are two conclusions — you can go the route of Tim Ferriss and “mini-retirements” or you can go with early retirement by way of core FIRE principles.

My personal story is a little different. I inadvertently built a personal finance blog that would be valued in the millions of dollars and found myself, at the age of 30, with the ability to “retire early.”

Even if I didn’t formally retire, the decoupling of work and pay was a big enough psychological step that I felt like I retired.

What I describe below is the moment and then months immediately afterwards, which were surprisingly challenging, and this transition period is what a lot of people don’t talk about when they celebrate early retirement.

You can try to imagine what that transition is like. Ms. ONL pondered this question of how well do we really know our post-retirement selves just recently and I commented that it takes time to discover your post-retirement self.

It’s not something you can envisage ahead of time but you can plan the discovery process.

This is a look into my discovery process.

Early Retirement and Rediscovery

There are two days in my professional life that I vividly remember.

The day after I quit my full-time job to work on my personal finance blog and the day after I no longer controlled it.

The day I quit my full-time job was the last day I ever used an alarm clock to get up for work. I woke up the next day, and it was a Saturday, excited and ready to get to work on my baby. My head was swirling with ideas and I was itching to get them on digital paper and into the world.

I was ready to get to work and work is exactly what I did. In eight years, I wrote 4,400 posts and over two and a half million words.

And I loved every minute of it.

The day I no longer controlled my personal finance blog didn’t feel much different than any other. It was just the culmination of several months of conference calls, meetings, and the drudgery of due diligence.

I hopped on the Amtrak Acela to New York, signed some papers, ate a delicious lunch, and rode the Acela back home with a bottle of Dom, a gift from my benefactors.

The two-and-a-half hour ride back was surreal. I sat in my seat with this box wrapped in shiny purple wrapping paper with a purple bow. I had just been come into more money than I’d ever seen in my life but I felt a little empty. The thing that occupied my mind was no longer there.

That’s what few people talk about when it comes to retirement.

You’ve been going to a place for years, working on projects with co-workers, thinking about those projects, being stressed out about deadlines and the work, and despite all that, you were doing good work and accomplishing big things. Then, in an instant, you’re not.

The next morning, I remember staying in bed for an extra hour because I had no incentive to get up. I was no longer excited.

It’s not an easy transition.

It took me a few weeks to break out of the funk. When people talk about how depression isn’t sadness but emptiness, I now understand. I was a little depressed in those weeks and months afterwards because I no longer had a drive. No reason to get up in the morning!

How did I break out of my funk? I stumbled onto a TED Talk by Simon Sinek that resonated with me. It was recorded just a few months earlier and it pushed me to ask myself why I work.

For me, the answer was always money — and then I stopped thinking about it. When I kept pushing, I realized that there were other reasons.

When I look back to my time in the corporate world, there were things I enjoyed about working. As I pondered my why (beyond money), I believe I had two more — accomplishment and learning.

The #1 reason I worked was for the money — we all need to eat, a place to live, and toys — but there were others now that money was satisfied.

But when you retire, money gets taken off the table as a primary motivator but it’s rarely the only one. I would later realize that learning was a proxy for growth and progress, which is itself a stand-in for accomplishment.

I needed to feel like I was working towards a goal, overcoming challenges, constantly improving in something, and building something.

For years, it’d been my blog. That was gone.

What I discovered in my head needed to be tested. So I challenged myself to pursue something I knew would give me a sense of accomplishment and learning.

I started playing golf. Golf is a wonderfully frustrating game with a steep learning curve. My dad started playing many years ago and I would watch him practice in our backyard. He would hit golf balls into a net and do it over and over and over again. For hours. It looked hard and it was very hard.

I had friends who loved it and so I had plenty of people to play with. Within a year, I could hold my own and not be frustrated the entire time I was on the golf course. No other game is measured by how frustrated you get.

As I improved, I did feel a sense of accomplishment. I felt like I was progressing along a learning curve. It checked all those boxes… but it wasn’t enough. A test of “why I work” revealed it was more than accomplishment and learning. Golf is fun but it’s just a game. There are no stakes.

In the end, I went back to “work.” I realized that money was still a powerful force but not in the way I originally thought about it. I wasn’t motivated by the accumulation of money, it simply put that work in the proper context and more readily provided feedback on my performance.

I partnered with someone to build a meal plan subscription business (we send PDFs of recipes, not physical food) that is doing well. I started a new personal finance blog, since my interest in personal finance never waned, and it’s growing nicely too. I added to the list of “things I wish I knew about business before I started it” and loved the challenges.

While those projects make money, my interest in them is more about building something valuable, learning how to help those businesses succeed, and hitting milestones I set for them.

Generating a personal profit is not priority one but it’s still important as a gauge of progress. It gives the project a sense of tangible value and that is still important for me.

Nowadays, I wake up excited to work on my projects. I may have “retired” years ago but I haven’t stopped working.

=============================

How I Would Do It Differently

All in all, things turned out great.

As I look back on my process, and think about how I might have done it better, it may be valuable to think about “encore” careers. It’s the career after your first one(s), the one that you hope to retire from early. It’s one where personal meaning and impact matter more than income, though it should still bring in some income.

A prime example of this is Bill Gates and the Bill and Melinda Gates Foundation. Bill Gates made a fortune with Microsoft and his second career in philanthropy brings him personal joy and fulfillment, while having an impact in the world.

There’s an entire body of knowledge about encore careers. There are even companies who will help you find the perfect encore career! (Though I’m not entirely sure those are necessary.)

If I were to do it differently, I would’ve planned my encore earlier. In my specific case, as an entrepreneur, I would’ve started building the next project on the side to get the ball rolling. Businesses take time to ramp up and those early months and years can be very difficult. When you’re spending hours and not seeing much progress, it’s nice to have a day job where I can get still that feeling of accomplishment and growth. I can have wins in other areas to cover the drudgery of the start.

If you’re years away from retiring, it pays to start thinking about it now. You want to be ready to enjoy retirement, not seeking to fill an empty space, and now is the perfect time to do it. Think of it like planning for a vacation — except it’s a permanent vacation from your 9-to-5. :)

We all need to be working towards something, whether it’s our golf swing or a worthy cause, and it’s important to find that “something” as soon as possible. There are a lot of hours in the day and finding ways to fill it may be harder than you think!

Jim Wang writes about money and personal finance at his new blog Wallet Hacks. You should check it out because it’s amazing. Oh and sign up to the free email newsletter so you don’t miss a thing.

Chime in!

What do you think about Jim’s idea of getting an encore career moving before you leave your first one? We’re already doing that with this very blog you’re reading, as well as a few other projects behind the scenes — we totally buy into the idea of smoothing out the transition that way. And can you believe he wrote 2.5 million words on his first blog?! That’s almost ten times as much as I’ve written here… and I have a LOT to say. ;-)