Why, If You’re Not Completely Satisfied, It’s Time To Quit Your Job

#noregrets, right? So why aren’t you relaxing on the beach with me on a Monday morning, or sailing through the Whitsundays on a Tuesday, or in a few months from now, exploring the Australian outback on a Thursday? Where are you?

Are you in your office cubicle? Are you looking at the clock? Are you thinking about everywhere else that you would rather be than where you are?

If you answered yes to either of those last two questions,

What are you doing and why are you doing it?

You can’t quit, you say? Well if you have a mortgage, kids, and/or some other big adult responsibilities, I have to admit that I cannot relate and maybe traveling like this isn’t going to work for you.

BUT if you’re in your twenties or thirties, have no mortgage and no kids, what’s your excuse for not making a big change to start loving your daily life?

Let me tell you what some of mine were and what some of yours may be:

1. Student loans: I am still paying these while I’m traveling, most of the time. I did pay ahead, though, especially when I was living at home and had more money to put toward my loans. Because of this, I don’t have to pay every month, but I try to so that I don’t have to deal with as much interest. The way I see it is that I am going to have to pay these loans for many years to come, so why miss out on other things that I want to do now? The loans aren’t going anywhere, so I am.

2. Car payment: I didn’t have this because I drove THE oldest car and refused to get a new one in fear of being stuck to any one place because of a huge expense, but one of my friends who is traveling does have one, so you can read about that below.

3. Rent: I waited for my lease on my apartment to be finished before I left the country. My last day at my job was only a week and a half before the lease was up.

4. A career (that maybe you don’t actually enjoy but feel like you should, and you don’t want to abandon it since it pays alright and you went to school for it): Obviously, I am defining that confused feeling about how to decide if what you chose to do when you were 18 is still the right career path for you.

5. Fear: It’s hard to give up everything and walk blindly into the unknown. It took me about a year of deliberation about what I needed to change in my life before I made my decision. At some point, you just have to jump and trust that you’re going to land safely somehow.

There will always be excuses, but if you’re not absolutely happy and you’re one of the people that constantly thinks about leaving your job or tells me how jealous you are of my current nomad life, make a move! You CAN do this! You CAN live a different life!


Okay, so maybe you don’t want to be a nomad, maybe you want to start a business of your own. Maybe you want to retreat to study a subject that’s completely different or change your career path or maybe you want to do something else entirely. In case that’s what you’re thinking, I talked to some friends who also quit their jobs to get some feedback about why they did it and what they are doing now:

Phil DiMuro- Former Sam Adams Salesman and Founder of Loople Mobile


Why did you quit your job? Ultimately, the decision came from inside. Since I was a child I always had a passion for entrepreneurship. From my first few volunteer opportunities with Relay for Life up until building Loople I’ve always looked at problems in unique ways. This has really helped me grow and develop throughout the years. When you have that passion it forces you to ignore all the reasons “not” to do something; “You are too young,” “Why leave a great job,” “Secure pay check,” “Steady Income,” “Challenging future with so much unknown” but deep down inside your gut tells you to ignore these things and take the damn leap. That is exactly what happened in my experience. I loved my job but I knew decades from now I would regret not doing it now so here I am in an abyss of the unknown… and I couldn’t be happier.

What is your plan? My goal in life is to spread positivity, creativity, and passion with everyone I interact with. I find that learning through others is critical to becoming successful yourself. My goal is to continue launching Loople Mobile and focus all my efforts on this (my first official startup). My end goal is to build companies my entire life. I love working hard and building something bigger than myself and that couldn’t be more true than in the world of startups. I hope to look back decades from now and say that taking this first leap is what helped create the man I wanted to be in the future.

What did your family think? Honestly, I’ve been amazed at how supportive everyone in my life has been. From my family, friends, my girlfriend. Everyone has played a part in motivating me to take these risks.

Are you scared of running out of money? Absolutely! To be honest this is probably my biggest concern and Dave [cofounder] and I talk about it daily. From everyone you talk to, they say starting a business takes twice as long and three times the amount of money you expect it too. Judging by that math running out of money is obviously one of my largest fear. With Loople our first round investors have allowed us to fund our development and marketing for another 6 months but my personal bank account doesn’t have that same livelihood. I’m driving for Lyft and Uber on the side to subsidize my bills and I have additional money saved for emergencies but I hope I won’t have to use this to keep myself afloat while Dave and I don’t take salaries or stipends. We are 100% independent from investor money and we plan to stay that way for as long as we can.

What have you gotten out of this experience so far? Well to start? Everything! The last two years building this business with my partners has been the most challenging, demanding, rewarding thing I have ever done. I’ve learned everything from how to legally register a business/trademark to guerilla marketing a local startup. Building a business takes everything you got and even though my business is very young I can say without a doubt… I understand why 95% of startups fail. Every day is a new challenge, a separate roller coaster to face, and the downs aren’t easy. It takes a lot of motivation to stay positive and focused. Online resources like TED, Live Unbound, and youtube videos of Successful Entrepreneur speeches help me stay positive. Local startup groups, your fellow entrepreneurs, and your closest friends and family help get you through this all. The biggest thing I’ve learned is build yourself a safety net of mentors, positivity, and support because that will help you get through the “down parts” so you can truly love the “up ones.”

How long did you consider it before you decided that quitting your job was the right choice? I’ve always known that when one of my ideas got far enough along I would need to make the choice so I’ve honestly been planning this for years but I’d say the last six months it was clear. I had enough time/money/and resources to finish building this project before fully launching it which was when I knew I needed to fully leave my day job to make Loople a success.

What are your plans for the future? Start bringing in money instead of spending money. Ultimately that’s my end goal and everything we do with Loople will be focused on growing our user base so we can eventually turn this into a truly successful business.

**If you want to get some real candid feelings, check out our “Baltimore Buzz” Blog article from Day 1 with Loople. This was an article I wrote off the cuff and I’m proud of everything in it. It really embodies how I felt after taking the leap of faith and I couldn’t be happier looking back today.

David Phelan – Former Project Coordinator and Cofounder of Loople Mobile


Why did you quit your job? After college, I jumped straight into the workforce for three years. I had a great salary, security, and lived right near my friends and family. Life was easy, but I gave it all up. I was presented with an opportunity to work with two friends on a startup business. I always wanted to work for myself and this was something I could not pass up. I knew that down the road I would kick myself later in life if I didn’t take the leap. I know it will be extremely difficult, but nothing is ever easy and I look forward to the doors it will open in the future.

What is your plan? Currently, I am working with a startup company called Loople. I moved down to Baltimore full-time to help make this business a success. I am not taking a salary for now and I am living on a very tight budget.

What did your family think? My family was extremely supportive. My Dad had success starting his own business and took a huge risk doing. I always admired this and wanted to follow in his footsteps. Aren’t you scared of running out of money? I am absolutely terrified. For the first time in a while, I can’t do everything I want to do anymore. I need to budget very tightly and every dollar matters.

What have you gotten out of this experience so far? After a month, I have learned the startup life is a roller coaster. There are days where it seems like nothing can go right and other days where you make huge breakthroughs with your business. It has been an incredible learning experience. Also, I always respected people who made this leap. However, I never thought I could do it myself. I have always made the smart choice, but I proved to myself I could step out of my comfort zone and take a huge risk.

How long did you consider before you decided that quitting your job was the right choice? Quitting my job was the hardest thing I have ever had to do. I was not scared about leaving the company, but I felt like I was letting everyone down. I had made so many relationships within the company that went so much deeper than co-workers. After many sleepless nights, I finally put in my two weeks notice. The moment after, I realized it was the right decision.

What are your plans for the future? Honestly, it is very difficult to plan ahead because it is hard to know where our business will be in a month let alone a year. All I can do is work as hard as I can to make Loople a success! I look forward to hearing what the future holds for us.

**Download the Loople Mobile App to support Phil and Dave!

Stephanie Lees – Former Server and Corporate Trainer, currently a self-proclaimed “Free Spirit”


Why did you quit your job? Most recently I was working at a server at a fancy French Bistro in the city [Philadelphia]. Mostly I quit because I knew that I could easily get another serving job…and that that place would most likely hire me again either way. This trip [to Israel] was only supposed to be 3 weeks. It ended up turning into 6 weeks completely by accident. I had been working at a fancy .com as a Corporate Trainer prior to being a server. I enjoyed telling people that I was a Corporate Trainer because I felt like it made my sound important and successful. In reality, I was barely making any money at all and I was totally being taken advantage of. I quit after finding out that the company was doing some business that I didn’t find so ethical. The only reason that I took the serving job in the first place was because I wanted something more flexible and was planning on going back to get my Masters.

What is your plan? My plan when I doubled the length of my trip was “why not.” I was offered room, board, and education on my heritage for free. That’s not the kind of thing that you pass up.
What did your family think? I didn’t ask what my family thought. I just told them what I was doing.
Are you scared of running out of money? I’m not scared of running out of money because I know that I’m not going to be traveling for that long anyway. I wasn’t living pay check to pay check in America and my expenses here are minimal. Anyway, if I needed money I could always babysit, clean houses, or tutor English and be paid under the table.
What have you gotten out of this experience so far? I found a new sense of self. It’s been incredibly deep and spiritual. I’ve been challenged and pushed and ripped open. I’m exploring a new lifestyle and a new sense of belonging. I’ve just spent 3 weeks in seminary (intense religious school) in Jerusalem, the holiest city in the world. I’m so happy that I opened myself up to be able to have this experience. It’s so easy to live without living and without ever considering why you are alive. People live with their eyes closed and their ears shut, worshiping money and the weekend; using people and themselves as objects. They stumble through life blindly without true purpose, tripping over their egos while staggering along as part of the herd. Instead of being at home working mindlessly and meaninglessly, looking for other jobs and binging on alcohol, popcorn and Netflix; I’m polishing my soul and reconnecting with my core.
How long did you consider before you decided that quitting your job was the right choice? After 4 months of being aware that I was suffering, it officially took me just under a month to gain the courage to officially quit my job. I knew it was the right choice right away because of the relief I felt at sending that email. Three days later I became even more sure that I made the right choice when I left work with a super swollen, very painful dominant hand. I know that you aren’t supposed to walk around looking for signs, but either way that was a pretty clear sign that I needed to move on
What are your plans for the future? My future plans are to be determined. I know that the way of the world is change and that opportunities come around all of the time. I’m reluctantly heading back to America in a couple of days because I still have an apartment and some other things to take care of. Besides that, I’m either looking for a job selling wine in America or I’m coming back to Israel to spend more time in seminary and on self exploration. I haven’t come to a decision yet on which path I will choose–I feel that there are really strong reasons for doing either. I’m gathering all of the information and putting it out there for things to fall into place–wherever they fall into place.
Advice about quitting your job from Steph: Life is amazing and you deserve the best of everything. If you aren’t satisfied in your life, if you’re unhappy or worse: you need to make a change. Absolutely it’s terrifying but it’s worse to live a shell of a shadow of a life. The world was made for you and it’s waiting to help you become the person you are meant to be. “Ships are safe in harbor but that’s not what ships are for”

Kelsey Karli– Former Social Worker from Pennsylvania, currently living in Australia


Why did you quit your job? I was working for four years as an adoption social worker in PA. I had always wanted to move out of PA and thought that after I was there for 2 years I would leave. I ended up staying longer as I enjoyed my work helping families with the process of adoption, paperwork, and getting to see the families interact with their new children during post visits. There never seemed to be a good stopping point to leave because I was always in the middle of working with families. I then started looking for social work jobs in CA in the fall of 2014, but did not move on the plans as I was not even sure I wanted to continue in the social work field. I found out about work and holiday visas in the fall of 2014 and decided that traveling for a year in Australia would be a better option at this time. I’m 27 and the visa is only valid for those up to age 30, so I decided now was the time to go.

What is your plan? I started looking ahead into the next year to figure out when I wanted to go and decided that leaving in April 2015 would be the best time. It was probably not the best time to leave from work during a busy month, but I would be able to finish reports and visits for a few of my families and then leave since they would be finished. Leaving for Australia at the end of April 2015 with the plan to return to the U.S. at the end of April 2016 seemed like the best option. I am a bridesmaid in my cousin’s wedding in June 2016, so I wanted to get back with a little time to help her prepare for her wedding. My plan in Australia is to just go with things as they arise. Being open to try new experiences, meet new people, don’t stay in an area for too long as I want to see and do so much during this year of travel.

What did your family think? I mentioned that I was thinking of doing this work and travel to Australia to my mom in November. She had always wanted to travel to Australia as well and just said I should do some research before going. When I saw my relatives at Thanksgiving, my cousins (who knew I wanted to move to CA) asked when I was moving to San Diego. I mentioned that I was looking into another option first and told a few of them that the plan was Australia. They were surprised, but thought it was cool, especially if I actually followed through. I mentioned it to my brother on the way home that night, he thought it was great. In Mid-February, as I was ready to apply for the visa, I told my dad my plan. He was surprised, didn’t understand why I was going so far, and asked why I just couldn’t go to CA. I then called my sister that next night and told her. She said she would miss me, but it sounds like a great opportunity. Once my visa was approved, I called my brother and sister to tell them it was a done deal; I was going. My sister started to cry and my brother was jealous and said he hopes he can visit. Mom is/was very supportive of this trip/adventure and while dad is just nervous I’m out by myself and so far away, he enjoys seeing the pictures and updates from my adventures. I am so grateful for supportive family and friends and I’m excited that some of them plan to visit me down under this year.

Are you scared of running out of money? I have had at least a part-time job since I was 14 years old. I have saved most of my money over the years, as I am not really interested in shopping for clothes or random items. I had a decent amount of money in my savings before I left for Australia to cover expenses for my visa, flights, an agency to help with the travel plans, and spending money in Australia. I also still have a car payment for my car back home, so I am aware of how much money I need to keep in my savings throughout the year for that expense. During the first three months I have been in Australia, I have actually only worked a total of 4 days. I have not really worried about my expenses as I know I have a cushion to use, so I have planned excursions, gone to a week of surf camp, gone out with friends, and attended sporting matches. I have taken advantage of free events in the cities, walk mostly everywhere to save on transportation, book longer stays at the hostels to save some money, and traveled on Sundays as it is the cheapest day to use the public transportation. There is also always the option to work for accommodation at hostels if needed and I’ll take whatever work I can find.
What have you gotten out of experience so far? This has been the best experience I have ever had so far. Traveling solo was a scary thought at first, but as soon as I arrived at my hostel, I met other travelers and bunk-mates that had just arrived. We paired up and explored the city, attended sporting events and shows, went to the bars, and participated in the events at the hostel as a way to learn more about the area and meet new people. During this experience, I have really tried to step out of my comfort zone and try new experiences and foods. Even though I was independent and living on my own back home, being here has forced me to figure out plans and finances, and really learn more about myself and what circumstances I can handle.

How long did you consider quitting your job before it was right choice? I had wanted to change my job by moving out of state for over two years. When I found out about the work and holiday visa in October 2014, I started researching over the next couple of months. I did not start any of the paperwork on the travel agency or visa until February 2015. My visa was approved the second week of March, and it was right after that I informed my supervisor and co-workers I was leaving. I gave a six week notice and left work the third week of April and was on a plane to Australia 12 days later.

What are your plans for the future? To be honest, I don’t really know. I know I want to continue traveling, and see more of the world. I at least have to go back for a few months for my cousin’s wedding, but then I’m not sure if I plan to move out to CA or if I stay close to my family for a little bit and work to save up before traveling again. I have met so many wonderful people while traveling who live in various parts of the world. I have made friends for life. I know I want to go travel through Europe soon and because of this experience I know I have places to stay and travel guides when I plan my next travels.
Advice about quitting your job from Kelsey: Life is about taking risks and figuring out who you are. It’s also important to see more of the world than just the few states around you. Learning new customs and immersing yourself in a new culture is important and helps you to grow as a person as you are exposed to many different types of people. I know stepping out of your comfort zone is scary. Leaving a professional job after 4 years to go travel might seem like a crazy idea, but this has been the best thing I have ever done. Go before you have too many responsibilities. Travel with your partner, friend, siblings, or go out on your own and meet some new people. The desk jobs will always be there when you get back. Realize that money is not the most important thing, but experiences are what will last a lifetime. And oh yeah, have some fun!!

These brave people took a big risk, but it was worth it. They don’t have it all figured out yet, but they’re happier because they shed the parts of their lives that weren’t allowing them to be true to themselves and their dreams.

As I’ve said, I was completely torn over what it was I could do differently to stop being one of those people staring at the clock, waiting for Friday, complaining about Monday, and constantly counting my vacation days to get out of my cubicle. And one day, after months of thinking about it, I thought F*** it. What did I have to lose, money? What was I saving for anyway: The big trips I wanted to take but didn’t have time for? A house someday because that’s an “adult” thing to want? I can’t explain how much I’ve changed in the past 3 months: I no longer feel the anxiety and stress that I once felt, I no longer have the burning desire to be anywhere but where I am, I no longer have to fake wanting to do what I am doing, and now I don’t have to wonder what else there could be outside of office walls.

I am working right now, in Brisbane, for the next two months before traveling again. I am working in places that are getting me closer to my goals, and I’m still making time for myself. I am also keeping in mind that if I ever feel unhappy in a job, I’m done. My philosophy here is that I can leave whenever I don’t like something, so I try to be very honest with myself. I’m working in the industry that most interests me, and I know that I can pick up and go whenever I choose. I’m not sure what the future holds, but I’ve learned that instead of over-thinking it all, it is best to just do whatever I feel is right for me at that time.

The reason I want to share these stories is because I want for everyone the same that I want for myself: to look back on life and be proud of the choices I made and the chances I took.

It’s time to be honest with yourself are you ready for a change?

steve jobs

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