My Story of Quitting My Job, Going All In, and Being Scared – Part 1

Going All In - Get Busy Living

I don’t want you to believe that my life is perfect. I’m not a fan of people online only show and write about the great things going on in life. Especially from people who write about personal development or how to make money online. They choose only to publicize what’s awesome about their life.

That can create a false sense of reality for all of us. It’s easy to leave out the struggles and only show the good stuff. It makes it seem like life should be one easy ride to the top. That doesn’t help us at all.

I like real people. People who will tell you how they failed before but also what they are doing about it.

Success isn’t just about the results you get. It’s about how many times you get your ass knocked down, but get back up.

I can do more to inspire you to take the action needed in your life by sharing what’s not perfect about my life and what I’m doing about it.

I’m no one special. I am not immune to problems, failures, worry, stress, and most of all fear. I just do my best to improve myself so that I can handle it. It’s not always easy, but the other choice is to let it get the best of me.

I have come a long way in three years when I decided that I was going to seriously turn my life around. I am proud of that, and my life has had many great moments. It’s also had its failures. I’ve screwed up. I’ve made dumb mistakes. I’ve sat on my couch cause I have so much on my mind and wondering when it’ll all get better.

About a year ago, I had to make a huge decision. One one hand, the decision would fulfill a dream. One I’ve been putting off for years. On the other hand, it would leave me with an uncertain future.

It’s been almost a year and I’ve kept my story silent because I wasn’t sure how it would turn out. I’m finally ready to open up and share what this past year has been like.

2011 – Life Changing

Many of you know my story that two years ago I released my first iPhone app, Photo 365 in August 2011. It came at a time in my life when I finally decided to take control of my life.

One year before that, in October 2010, on a drive home from work, I decided I was sick of the person I had become. I hated my job working in the restaurant business. I hated myself. Why was I unhappy? How in the world did it get to this point?

I made a decision to stop all the shitty excuses and laziness that night. I wrote a letter to myself and taped it on my wall. Fast forward to the following year and the app came out. I was just so happy that I actually started and finish something. If I didn’t make one dollar, the whole process was a great learning experience.

Then I was in for the biggest surprise of my life. My app got featured by Apple, not one week, not two weeks, but three weeks in a row.  It reach rockstar status when it was App of the Week.

I earned about $30,0000 that first month. I couldn’t believe that this was happening to me. I had struggled to find ways to make money online for many years and now I had a way.

That money didn’t go in my pocket. I ask my parent’s accountant what should I do so I wouldn’t have a huge tax bill next year and he said create a LLC. That’s what I did and I officially had a business.

I remember someone online asking me if I was going to quit my job. That was the ultimate goal. I had been wanting to do that since 2005. Quitting my job right away didn’t cross my mind though.

If I had won millions of dollars I would have, but I knew realistically that I wasn’t going to be earning an average of $1,000 a day forever. So I was going to wait until my sales continued to do well enough that it could cover my living (mortgage, insurance, all that stuff) and have money left to invest back into apps.

That was the ideal situation. Be able to pay myself every month, and have enough to spend on my apps.

How long would I wait? I wasn’t sure. Not too much loner I hoped. I wanted to see how Photo 365 would do.

So I kept working in the restaurant business. The job I hated. The one I’ve been trying to leave. The one that made me feel sick to my stomach driving to when I had to work. The one where I worked nights, weekends and holidays. How bad did it get? I grew to hate Christmas. It used to be my favorite holiday, but when it was Christmas I knew I had to work and it would be busy.

Despite having that app, this blog, and a new attitude about life, my frustrations about work remained the same. Not having a definite date when I could quit made it worse.

I did not want to quit yet because the security of a paycheck. It was my worst enemy! It was so hard to give up. With a paycheck, I knew how I was going to pay my bills every month. Without it, I wasn’t sure.

2012 – Waiting is the hardest part

Life wasn’t all bad though. I got married in October 2011. In 2012, I wanted to travel more since we were married. My wife and I drove up the coast from Los Angeles to San Francisco and went zip lining and white water rafting in Costa Rica. We took short trips to Atlanta and Orlando.

The job I hated did have one benefit and that was taking multiple vacations. I always hated coming back home, because the next day I’d have to go right back to work.

Photo 365 was consistently earing $50-100 per day. Doing some quick math, it seems good, but not enough to quit my job. The money I did earn mostly was going back into new features. One that would hopefully increase sales.

I started seeing other apps similar to mine enter the market so I had to try and stay on top.

I turned my focus into making more apps. I thought with more apps, I could have more revenue every month. I spent money on new apps like Gratitude 365, Bucket List, and Life Quotes.

It all didn’t turn out so well.

Gratitude 365 has done okay, but never got featured and took off like Photo 365.

Bucket List and Life Quotes have bombed. I researched the bucket list market and thought I could enter with a better version. I screwed up by hiring a designer and then not using any of her designs when she was done because it didn’t look good. The next guy I hired didn’t do a good job. Finally I found a good designer.

When it was all finished, I just didn’t like how it turned out.

The life quotes app started as a Bruce Lee quotes app, but I had to change the name since I didn’t have permission to use his name. I loved how it turned out, have gotten great feedback, but from a revenue standpoint, I could just buy one new pair of shoes.

So both those apps bombed and costs me thousands of dollars. An expensive learning lesson.

I was getting frustrated. 2012 was supposed to be the year when I could quit my job. However, app sales weren’t improving. I was losing money instead.

For 2012 my apps earned $27,548. Better than nothing, but not what I had hoped for. Even if I withdrew that money and didn’t spend a single penny on outsourcing, it’s not enough to live on. I was spending most of it on updates and new apps so I didn’t have much left over.

Towards the end of 2012, I didn’t know how much I could keep working.

If you are or were in a job you hate, you know just one more day is way too much. It is a struggle to get in the car and make the drive to work. There would be days when I wished for an accident just so I didn’t have to work. Yes that’s how bad it was.

Despite some failures, I didn’t give up on apps. I kept believing it’d get better. I reminded myself to be patient. Waiting was the hardest part.

2013 – The Big Turning Point

In 2013, I did have one thing to look forward to. My wife and I had our big trip coming up in January 2013. A trip of a lifetime. We were going to go back to Taipei and from there travel to Sydney and Hong Kong. All flights in business, first class, and even in a private suite. All free because of the points and miles I collected for one year. I had been waiting for that trip since the day I booked in July 2012.

We were going to be gone for four months. I couldn’t wait.

I could not ignore the reality of my situation after those four months though. Was I going to go back to work just so I’d have the security of a steady paycheck? Or finally quit, be free, and go full time with blogging and apps?

Some people are fortunate that they know they are ready to quit their job because their side business surpasses what they are currently making. It makes sense to quit and financially it’s a seamless transition.

Some don’t have that luxury. They quit their regular job before they have a backup plan financially. Sometimes it’s a leap of faith.

Sometimes they get laid off so they have no choice.

I didn’t want to use my savings, but I would have to until I could reguarly pay myself from my business. When would that be? I still didn’t know.

My wife had been trying to find jobs, even entry levels, but couldn’t get hired. So weird. Maybe I married a secret criminal.

I didn’t want to work another year. I didn’t want it to be the end of 2013 and thinking about wasting another year in a job I hated. I would be so mad at myself. I could not wait for the perfect time anymore.

I’m gonna do it!

I made the decision to not go back to work when I came back. I was going to go full time with my online businesses. If I had more time, I figured I could get more results. I would also be much happier not having to go to work.

However, I have said I was going to quit before, but chickened out.

2007 – 2009

I went to Taipei in 2007 to study Chinese. That is around the time I began to hate my job. I didn’t know what else to do. No other job I looked for online interested me. I hoped by going away, I’d figure out what I wanted to do with my life.

In Taipei, I stayed 1.5 years, learned Chinese, had a great time, and met my future wife.

My goal was figure out what I wanted in life, and find a way to make money. I read The 4 Hour Work Week in Taipei, and it changed my whole attitude about work and life. I really wanted an online business that I could run from anywhere.

I did not want to be working at the restaurant when I came back home. No way in the world. I’d rather die than do that. My hope was that I would find ways to make money online while I was away.

I tried some different online businesses, but they all failed. I got caught up on how much money these gurus promised I could make and thought it’d be easy for me. I didn’t work hard enough though. I lost interest quickly.

One major problem was my lack of effort. Why? Because I didn’t have a deadline. I had no idea when I would move back home. I just kept extending my stay because I was enjoying it there. I thought I’ll figure it all out before I come back home.

In January 2009, after 1.5 years living abroad, I came back home.

Did I have a thriving business online? Nope. Not even close. I no plan B,C or Z. I had bills that needed to be paid every month. I think you know what I decided to do.

I went back to working at the restaurant. My life went right back to how I left it.

Back to 2013

Fast forward to four years later and I saying I’m going to quit my job again. This time was different. I did have an online business. It did really well when it first started, but 2012 didn’t make enough for me to quit.

Now it’s 2013. If I wasn’t going to quit now, when would I? When everything was perfect? I didn’t know when that was going to be.

I really wanted to be free and not keep wasting my life doing something that made me so upset.

I had been waiting so long for the right time to quit. It was a scary choice to make. I had money saved, some stocks and mutual funds, but really didn’t want to touch it. I would have to though if I quit.

Would sales of my apps increase in 2013? Could I finally pay myself from my business? Or worst case scenario I go through all my savings and then what?

I knew I could have stopped spending money on updates to Photo 365 and Gratitude 365, but I believed sales would increase with more improvements. Maybe it would be a stupid decision. Maybe I should have stopped pouring money into them. As CEO of my life, it was a decision I felt was right to do.

Just to give you an idea of my apps sales from January 1 to May 31, 2013 I earned $15,685 which averaged to $104 a day. It’s good, but that money was going back into the business. I had a major update in the works which would use iCloud to sync photos between the iPhone and iPad app. I felt this feature would make my app stand out even more from the competition. It took a long time to get it working right and that meant and a lot of money.

If I could double my daily average then I would feel more comfortable. About $6,000 a month sounds a lot better. I’d have money to reinvest and could pay myself a little.

I just didn’t know when that would happen.

In late May 2013, we came back to Jacksonville. My wife asked me if I was going to go back to the restaurant when we came back. I liked the twice a month paychecks, but I hated spending just one hour at work.

No more waiting for the right time. I would figure things as as I went along. I thought if my back was against the wall, as it would be without steady income, it’d make me work even harder.


No turning back. No second guessing. No more paychecks. It was time to go out on my own.

My mom, who is the boss, was supportive. She knew my frustrations, but I know she didn’t want me to quit because it’s hard to trust people who work for you. She could trust me, but I’ll be the first to say I was a lousy employee. I did my job with no passion. I spent as much time as I could on my iPhone, iPad, or reading when there was nothing to do. I felt like being there was a huge waste of my time so I kept myself distracted.

If I had an employee like me, I would have fired him a long time ago.

Now I was in the position I’ve always wanted to be in. No more going to the restaurant. Freedom! I had more free time now, but would I fill that free time with ways to increase income or worry all day long?

I only had 4-6 months of money saved up before my savings would go empty.

In the next post, I’ll tell you how it’s been since I quit my job. I’ve had doubts. (Update: Here is part 2 of my story.) 


Photo by Play among friends

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  • Yo Benny! As a casual observer, may I ask how your relationship is with your mom? From my viewpoint, if your mom is your boss, then surely she’d accept you back and pay you no? If so, perhaps you are being overly stressed?

    If it was a corporate job, that would be one thing, but surely there’s an open door policy with your mom no?

    • Hi Sam, great question. My mom would accept me back in a heartbeat if I said I wanted to go back full time. But I’ve been wanting to get away from being there full time since 2006. That’s a long time of hoping and finding a way to support myself.

      Maybe it’s hard to convey what it feels like when I’m there and doing the job required. It’s not fun for me, even for one day. Lots of reasons.

      Once I quit full time, going back full time was not an option for me. I didn’t want that safety net. If I thought that way, maybe I wouldn’t work as hard to make it on my own. I wanted to move forward instead of looking back.

      • Nice to know your mom isn’t a tyrant! 🙂

        Well, if you’ve been wanting to quit since 2006 AND you’ve got this financial free pass, than the paralysis has to be you then, no?

        If my parents had a business where they’d always hire me back, and I knew I would never starve, and I knew I could one day take over the business, then I would go ALL OUT b/c there would be nothing to lose!

        Am I thinking about things wrong? On the flip side, b/c I had no backstop, I worked my ass off on Wall Street and then worked my ass off the first year of “retirement” on my site. I still work hard online b/c there is nobody to save me…. although that’s becoming less true now that there’s a free home to go home to back in Hawaii.

        • Well she can be a tough boss. 🙂

          Yes I was definitely holding myself back. Back then, I had no idea what I else I wanted to do. I definitely looked for jobs but nothing seemed interesting to me. So I was definitely scared to just quit because I didn’t know what else to do. But later on, after I had my first app, I was my own worst enemy. I had a way to make money and if I went full time on it, maybe I’d succeed. However, I was just scared. I had doubts. I’m human. I kept hoping that my online income would match my real life income and then I could quit without worry.

          Also taking over the business was not an option for me. I don’t want it. It’s not for me. I know the amount of work and stress involved and it doesn’t matter how much money I can make from owning a restaurant. I’d just rather not. 🙂

          • Gotcha. OK, I agree. It seems like you were your own worst enemy. You’ve got like the IMF and the US Treasury behind you man. You CANNOT fail!

  • That’s pretty interesting

  • Samuele

    Benny, with you I discover the blog world (I’m italian, it’s a bit different here), and I was waiting for this post series for a long time. I love it. When the next? When the next? 😉

    • Thanks for reading! The blog post will come out the following Monday. Was hoping for today but it’s not ready yet. Stay tuned! 🙂

  • Great post Benny! Thanks for your transparency and being so honest. I know exactly how you feel about the tension of leaving a “regular” job and wanting to break out on your own. I work in a job right now that is mind numbing and, sadly, I’ve become an expert at distracting myself in the hopes it will get better. 2014 is the year where it finally ends and I make this work come hell or high water. I look forward to your next post and thanks again for sharing!

    • Thank you Bob. I wanted to write this because I know there are people in situations now that I was in a year ago. Next part next week. Wanted to finish it for today, but it’s not quite done yet.

  • Sally Yan

    Looking forward to part two.

  • Marina Reede

    Hi Benny! I am excited to read more (as I always am!)! Also, I finally got an iphone a couple weeks ago so I just got your gratitude app tonight 🙂 Thanks for sharing your story and all the motivation!!

    • Always great to hear from your Marina! Thanks for downloading the gratitude app! Hope it changes your life. 🙂

  • Sue Hull

    Hi Benny
    Your story is very interesting and very enjoyable to read. You are on ‘your’ journey at long last, stay strong and keep working on it, you are amazing.
    I have worked from the age of 17 and now 64…from small and large corporates,
    three of my own businesses and contract work in the south pacific. I am now working on a web site for my own ‘Life Coaching’ business to support clients in food, body and mind which in the pinnacle of change. The best fun at the moment is the creation of a web which is ‘me’ for my clients…love helping people.
    Looking forward to your next story
    Cheers Sue

    • Thank you Sue. It sounds like you’ve been able to do really well during your life and now living on your own terms and you’re making a difference in people’s lives. Thank you for the motivation to stay strong. I definitely will because there isn’t another option for me. No turning back.

  • Sue Hull

    Benny I forgot to mention I have failed in my life many times.
    Rebuilding financially, relationships, health and work. These are stories that have made me who I am today. Strong, confident, wise and flexible. I am very aware of who I am and what I want and with intuition, creativity and support in business at long last I feel free. I know it wont take you as long as it has for me.
    Money can give you comfort but very rarely does it bring happiness. Be passionate
    and happy with your courage to change.

    • Thanks for adding that Sue. Hope anyone who reads it will be inspired that even when life gets down, there is always a way back up.

  • Tomi

    Thanks so much for this post Benny. You really inspire me to make changes in my life. I listen to your podcasts everyday for motivation. Can’t wait for part 2 of this story. Thanks again

    • Thank you Tomi! That’s the result I want with anything I record or write. 🙂

  • Hey Benny, great story, and thanks for sharing! Even though it sounds like the conclusion is still unfolding, it sounds like it’s going to have an amazing next chapter. I’d like to share with you something that you may not have considered as an option: relocating to Asia. Josephine and I have lived the last 3 months in Chiang Mai, Thailand…where a studio apartment with wifi and utilities runs about $250…per MONTH. Two weeks of app revenue will cover your housing costs for a year! Food is cheap, and western food is always available(albeit closer to food costs back home in the US). And there is a huge community of American expats doing online businesses, yoga teaching, blogging, you name it. If you don’t mind a bit of adventure and getting out of the “comforts” of the US…you can focus on building your business/apps without the added stress of higher costs of living in the US. Then when you hit your big payday…you can look if it makes sense to live in the US again.

    • That is cheap!! If we move to Asia, it would be back to Taipei though, where living cost is cheaper than the US but certainly not as cheap as where you are.

      Reasons being wife’s a single child and her parents live there. She wants to spend time with them. It’s home for her. She keeps hinting about moving over there, but it’s tough for me. I like my comforts of living here, but at the same time lots of great reasons to live there. We’ll see! Are you two going to WDS this year?

  • spurthy

    It feels so pity that life is of full problems , which one cant ever know from their own life

  • Mike Wong

    I would be more inspired if you were making no money from your app and quit a job where your mom wasn’t the boss. $27,000 is not a lot of money but some people make that in one year working full time and they get by. Plus you had savings.