You've pulled yourself out of debt, are saving a reasonable amount of income for your retirement, have built an emergency fund, and your daily needs are easily met with your income. Congratulations! Now what?

That's exactly where I was in 2007. I sold my business and generated a huge windfall — over a million dollars. I paid off all my debt. And then I looked around and said, “Oh, crap.”

I had absolutely no idea what to do with my money. Previously, any extra money I'd earned was immediately stuffed back into my business, and I had been running deficits nearly everywhere. This was the first time in my adult life I'd ever had my head above water, financially speaking.

Over the next three months, I proceeded to blow over $50,000. Oh, don't get me wrong — it was fun! I bought a new car (that I still drive), some really beautiful artwork from artists I loved (that looks great on my walls), and thousands of dollars in clothes, new furniture, and other indulgences, such as $4,000 custom hand-made stereo speakers (that I'm listening to right now.)

It was fun…for a couple months. Then it got boring.

My Spiral Into Depression

Like many lottery winners, I spiraled into depression. The business I had spent six years of my life building was gone. I felt adrift — like I had no purpose. Despite having been “successful”, no one knew who I was. I had marginalized most of my personal relationships in favor of growing my business and working myself to death. And money wasn't going to buy me out of the situation.

Slowly, I pulled myself out of my depression. I realized I had the opportunity to make myself into anyone I wanted to be. I could do anything I wanted. I had complete freedom. The thought was both exhilarating and terrifying.

I bought a shelf full of self-help books and read them all, relentlessly seeking to answer the many questions I had. Some of them were philosophical, like “What made me successful when so many others have failed?” Some were practical, like “How do I invest my money?” But all of them led back to one deeper question: “What should I do to be happy?” I soon realized the latter question was incorrect. The better question was, “Who should I be to be happy?”

In December 2007, I started blogging. I exposed a significant amount of my business life and thoughts. I wrote about my successes and my mistakes and failures. I enjoyed writing, doing videos, and interacting with my readers. Helping others figure out their purpose, their businesses, and their websites and blogs was a fantastic experience.

Spending With a Purpose

I made a point of trying to achieve greater states of happiness on a daily basis. Instead of being merely content — or even apathetic — with my current state of being, I realized I could be happier daily. And suddenly it hit me: I understood what I wanted to do with my money. I wanted to outsource pretty much everything I hated doing.

In order to live a simpler, calmer, but more effective life, I had to drop the shackles of wanting to do everything myself. To allow time to meditate, think, write, and create, I had to get rid of the drudgery of daily tasks. I realized my money could serve a fantastic dual purpose: To allow others, whose passion is cooking, cleaning, or assisting in various ways to help me — while I supported them by giving them income to do what they loved.

My life fundamentally changed that day. I started hiring people to do everything I didn't want to do. The first step was to hire a cleaning service. Then I hired a personal assistant to work out of my house, filing papers, doing laundry, and organizing. I hired virtual assistants to do all the menial tasks I hated doing: bookkeeping; video editing; audio editing; even setting up my Facebook fan page. (Lisa, my VA who set up the Facebook page for me, said happily: “I can't believe I get paid to do this!” And I realized…we're both lucky.)

My Daily Routine

I wake up in the morning and my VAs have sent me their updates. I am building a business where I create how-to videos for small business owners and bloggers who want to drive more traffic to their sites and get more customers.

I learned meditation, and currently spend about 40 minutes a day relaxing. I also spend a few hours a day doing the parts of my business I love, from creating videos to writing to programming. When I walk down to the kitchen, it's clean; Elia, my housekeeper, comes in every week to make sure it's spotless. She spends 2 hours cleaning our kitchen; total cost to me: $30.

My VA in the Philippines edits my videos and does a fantastic job for $3.33/hour.

Whenever I do an interview with another entrepreneur, I send it to another VA in the Philippines, who, for $9/hour, edits it perfectly, getting rid of all the strange pauses and “um”s. I send the edited interview off to a transcriptionist. For less than $30, I get back an excellent transcription, often 12-16 pages long.

Lisa, my VA here in the U.S., has set up an entire website and integrated it with a shopping cart for my customers to order products and access them once they have ordered. She charges $30/hour (my most expensive staff member) and she's worth every penny.

I treat my staff members well, and they love the fact that they can work from home and get paid great wages ($3/hour in in the Philippines is equal to about a $65,000/year wage here in the U.S.) They are happy — I can see it in their emails and text chat messages.

My partner Richard and I fight less. There's no scrapping over who will do a certain task. If no one wants to do it, we work together to figure out how to hire someone.

A Disease Opens My Eyes

I was recently diagnosed with Celiac disease. The management of the disease may sound simple, but it's not: eliminate wheat, oats, barley and rye from your diet. Most restaurants have very
few gluten-free items; I'm lucky if I can order one non-salad item from a typical menu. Some restaurants are impossible to eat at; soy sauce, for instance, has wheat in it. I've gotten sick from things as odd as bacon, cake frosting, and ranch dressing.

After a few weeks of eating mostly hot dogs and tuna fish, I grew tired of my limited options. I thought about learning to cook, but it wasn't something that excited me. So we hired a personal chef to cook our meals — one who understands the challenge of cooking gluten-free. We pay her $10/hour, including travel time to deliver the food to us, and she gets a fun side job.

In a randomly-chosen week before I hired a personal chef, I ate out four times and went to the grocery store twice. I spent a total of $179.91 on restaurants and groceries. Last week, I spent $215.49, including groceries, for eating out and paying my personal chef. My “eating out” expenses dropped from $86.14 to just $32.28 — over 60% less! My total spent was $35.58 more, but to me, that's a small price to pay for gourmet food of my choice delivered to my door. Another remarkable and unexpected side effect was that I no longer have an urge to go out and spend money at fancy restaurants — I simply ask my chef to make what I want and deliver it to me.

It has been more than two years since I sold my business, and I am happier than I have ever been. I made different choices than most: We rent a house instead of owning (a savings of nearly $4,000/month in our neighborhood — more than our monthly rent payment!); we only have basic cable; we don't have a landline, credit card debt, car payments, or student loans.

I chose, instead of buying more Stuff, to live a more fulfilled life. For me, even more important than holding onto my money tightly was to learn to let it go — to give it to others in exchange for work well done, and to trust that they could do tasks well. It's one of the best decisions I've ever made.