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Entrepreneur Stories of Quitting 9 to 5 Job

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39 Successful Entrepreneurs Share One Tip To Quitting Your Job and Running Your Own Business

December 19, 2016 By Neil 5 Comments

I knew within a few months of landing my first job after university that I wanted to quit and run my own business.

I had my first taste of business during my first year of university when I was 19, I setup a company that served shisha (flavoured tobacco) at club nights around London.

I felt on top of the world. I was making money and enjoying myself. Something I had not ever experienced.

That's the one thing I really miss, working on something you are so passionate about that it doesn't really feel like work because you are having so much fun! 🙂

See, there are times in investment banking where I genuinely think, “it’s been a good day” and feel motivated on my way home from work.

But that’s only a few days in a month.

I want to be able to enjoy every single day of my life, and retire knowing I’ve loved how I got there.

And that my friend, is why I plan to quit by the end of this year!!!! Yes planning to QUIT by the end 2016!

Taking the plunge to quit my job however is not going to be an easy one and I didn't come so close to making this decision overnight. It took me a long time, sleepless nights, and a lot of hard work to set up the foundations of my business.

I know that many of you are also going through the same journey and are in the process of taking control of your own destiny. Therefore, I figured it would be very useful for us to get one tip from 39 successful entrepreneurs who have already been through this stage of the entrepreneur's journey.

The advice is friggin awesome and so inspiring, you’re going to love it.

Brennan

​

Firstly, understand that you’re selling a product or your time as a service. Unlike being employed where you are selling your experience in that role, with your business it’s more transactional, and therefore you are selling an outcome. Brennan used to do web development for companies, and said he wasn’t selling web design as that’s just a tool, but what customers really wanted is the ability to get enquiries or sell online.

Secondly, realise the relationship between how money changes when you run your own business. As an employee, your salary is the final amount that goes into your bank. As a business owner, you now have expenses and overheads to pay. Your revenue is not the final balance in your account and therefore it’s important you plan your finances accordingly.

This leads onto the third point. With running a business there are a lot more less glamorous tasks than you might first think. Brennan cited, The E-Myth book (it’s on my books-to-read list) and he mentioned an example where a lady was looking forward to running her own bakery, but only after a few months she was miserable. She enjoyed baking but not the other things that go with running a business, like, accounting. (sorry accountants out there). That’s why Brennan recommends having a plan in place to manage all the bits that go into running a successful business and possibly getting experts in these fields to help you.

Lastly, you need to have an action plan and implement it everyday. You’re not going to have this huge profitable business tomorrow. You need to show up everyday, and overtime that stacks up into a big result!"

Brennan helps freelancers and consultants grow their business. His one goal is to make you better off than you were before you met him. Double Your Freelancing.


Ryan Robinson

Don't launch until you have a growing, sustainable number of paying customers. I learned this lesson the hard way and ended up having to move in with my parents just a few months after quitting a job and banking on the quick success of the side business I had been working on at the time.

A few years down the line, I'm now back to being self-employed. My personal rule is that I'm not allowed to quit my day job until my side business is generating at least 75% of the amount of income my day job also pays me—that way I'll be able to make a smooth transition without much change in lifestyle and spending straight out the gates. I'm confident I'll be able to pick up that extra 25% (and beyond) relatively quickly after unlocking a significant amount of time to work on my business full-time, but if you've never worked for yourself before, that can be a risky gamble.

It takes a lot of discipline and a rigorous routine to stay on track with your business goals. When it comes to calculating your income percentage that your side business needs to be bringing in, it can be different than mine, but it should be based upon your risk tolerance. If you have a family, dependents, or you'll be incurring a lot of new expenses (think: health care, self employment tax, office space, online tools, unpaid vacation or sick time), then you have more to consider—your savings cushion and side income level may need to be larger.

It's a very real possibility, especially if your business is less than a year old, that it'll end up growing much slower than you expect or plateau at the exact wrong moment, so it's important to protect for the downside.

The last thing you need when you're trying to grow your new business is the pressure of struggling to make ends meet.

Ryan Robinson is an entrepreneur and content marketing consultant. He teaches over 200,000 monthly readers how to start and grow a profitable side business on his blog, ryrob. This month, he's also challenging himself to build a completely new business from scratch in 30 days, in his Validation Challenge.


John McIntyre

Why do you want it? If you kinda want it, then you won't get it. If you REALLY want it, then you'll get there eventually (assuming you don't randomly get hit by a bus ;D).

I wanted to quit my job and start a business because it meant I could earn money ANYWHERE in the world, with nothing but my laptop and an internet connection. That is extreme freedom. And with that freedom, I wanted to do interesting things... travel, make music, learn languages (I'm currently spending a lot of time with music).

So why do you want it?

You've gotta dig deep inside yourself and figure that shit out. It's no use looking for the answer in a book, or in my story, or in any place other than inside yourself.

And when you've figured out what you want, you need to be sure that a business is the best way to get there.

Because hey - maybe you'd be better off moving to Silicon Valley and joining a startup (if you want to change the world, say), or getting married and having kids (if you care more about love than freedom).

Life is short. Do what makes YOU happy. If business is the vehicle to get you there, great. But if it isn't, don't let the hype and glamour around entrepreneurship make you ignore what YOU truly want deep down.


John is The Autoresponder Guy. I help people who are sick of the rat race become freelance copywriters even if they have no experience. The MC Method


Michelle Schroeder-Gardner

​My top tip would be to start your business on the side first, if you are able to. Doing this will allow you to fully test your business idea, while still having the comfort, stability, and income of your full-time day job. This will lead to a lot less stress as you'll still have a day job to fall back on while you test different business ideas!

Michelle is a personal finance blogger at Making Sense of Cents, where she helps people earn more, save more, and live more. She shares how she earns over $100,000 per month.


Eli Seekins

Quitting your job is exciting. But it can also be depressing and stressful if you don't meet your goal. I know from experience. If you plan to quit by a certain time and don't make it, it sucks.

When I finally quit my job, I sort of just went for it, and only had about 1 month's worth of savings.

I'm a risk taker at heart, and I believe that sometimes you just have to take a leap.

But I don't recommend that route for everyone.

The safest way is to build a side hustle. Like a blog for example.

It takes a lot of work, and a lot of sacrifices. You'll have to give up hobbies and being social. You'll have to spend all your free time working.

And then once your side hustle is making enough money to support you, then quit your job.

It's tough. But totally worth it.

That moment when you finally reach your goal feels amazing.

Don't try to rush it. I made that mistake. It takes time. You have to be patient, and you have to be determined. 

Eli helps entrepreneurs make money online. He’ll help you start your blog or business with a boom, get noticed quick, become an authority and make the money you deserve. Launch Your Dream


Joshua Ballard

Moonlight in your evenings before taking the final plunge, but remember that you will probably never feel 100% ready. Take the leap of faith before you know for sure. Otherwise you will just keep changing the bar on where "ready" is.

Founder of Paradox Marketing, an Inbound Marketing Agency in Australia. When he isnt out combing his close proximity for the perfect coffee he is trying to find a way to make his PC accept even more monitors.


Minuca Elena

Start your business while working in a full-time job. You will not earn a lot of money at the beginning from a new business. It takes time until you learn how to do a service that you will provide or create a product you will sell. Even then, you have to invest time in building an audience, create a brand, growing a subscribers list, pitching to clients. It could take a few months until you earn the same amount as your salary. That is why you should start your business part-time and resign from your job only when you earn enough money to support your monthly expenses.

 Minuca Elena is a freelancer that create expert roundups. Her posts provide quality content, bring huge traffic and get backlinks. She also helps bloggers connect with influencers.


Siobhan Johnson

Think things through and ensure you have enough savings, and potential leads for your business. Things take a lot longer than you think to gain momentum - an extra six months working my day job and working on my business at the weekends would have given me a lot more security and a lot less headaches. But things gaining momentum after a while is the natural way of things - anyone who is an overnight success is a) lying b) spent months before they launched practicing and c) burned out after a month.

Siobhan Johnson quit her (first and only) 9-5 after less than a year to run her Tarot, crystal and healing business, and her second business, a coaching and freelance writing business.


Roxanne Chia

Have enough savings and someone on whom you can count to support you (not only financially) for the next one year while you build your business. Have a Plan B as well, in case things don't turn out the way you want or expect them to.

Roxanne recently quit her full time job in teaching to pursure her passion in jewellery Trouvee.Co, and beauty blog, The Skinny Scout.


Katie Gannon

Get really clear about your choices and next career steps. Scientific findings suggest that you make better career choices when you use a combination of a system for dealing with all of the relevant information and your intuition to make the right choice for you. If you are struggling to make a decision, ask for support.

Katie helps professionals and graduates to change career through 1:1 support, CV reviews, courses, articles, resources and inspiring stories. Grown Up Learning


Renee Groskreutz

Don't be distracted by new ideas. Pick a focus and give it everything that you have every single day. When you hear a good idea, write it down and tell yourself that you can investigate it at a later date.

Your Answer Finder-Outer and chief cook and bottle washer at I Teach Blogging WordPress Support & Maintenance. Podcaster and speaker too because I love it all.


Andrew LeBaron

Take action today and follow someone who is already doing it.

Andrew buys and sells, fixes and flips, and holds real estate. True Freedom Achievers


Raelyn Tan

Don't quit until you have a complete business plan - what you'll be doing each month, how much you're expecting to bring in, how much money you need etc.

Raelyn Tan is a blogging and digital marketing strategist.


Benjamin Tyler

Stop trying to compete in the online world and focus in your local community. It is easier to enroll clients and get paid your real worth when you network in-person.

Also, when building out products and services, start between $1,500-2,000 USD. Don't short change your value and abilities. You deserve to get paid and surround yourself with clientele that wants to invest in themselves. There is a threshold between those that are searching and those that know they want to take their lives to a new level. It is in-between this price range where you will find those that want to make their vision a reality. 

Benjamin Tyler is the founder of Client Enrollment Academy, which helps coaches, practitioners and service based businesses master the client enrollment process.


Kayla Sloan

Save as much money in your emergency fund as you can before you quit. This will give you peace of mind if your business doesn't take off as quickly as you are expecting.

Inspiring others to talk about money as openly as we do. We’re sick of it being a taboo subject. Financial Conversation


Colleen Davie Janes

Have a product and a viable plan to get out there and make money asap. Don't quit without knowing exactly how you can make money right away. Otherwise you will become desperate and end up back in a 9-5.

Owner of Ace Your Video, that creates high quality, cinematic videos for entrepreneurs and local small businesses. Also offers coaches a DIY Video Course, and helps transition successful entrepreneurs into online video.


Rebecca Harpain

It is easy to forget that there are 7 BILLION people on this planet. No matter how small of a town you live in, the internet makes it possible to find the people who want to pay you for the gift you can give to this world. Don't rob them of the chance to work with you because your 9-5 covers the bills.

Rebeccaca works with entrepreneurs who have a clear direction for their business, but aren’t confident that their web presence shows how amazing they really are. Dual Arrow Marketing


Erin P.S. Zimmerman

Don't wait. Each of us has a different path when it comes to how and why we quit, but as soon as you feel yourself being unfulfilled in your current role/situation in some way, make a plan, and leave. I am not saying don't give notice. Give plenty of notice. To yourself, your employer, and your colleagues so that everyone can be prepared. But don't do what I did and stay unhappy and feeling stuck for 2 years after realizing what you are doing isn't for you. Know that you CAN make a bigger impact, and the quicker your prepare, the quicker you can start!

Erin helps business owners leverage social media to connect with their ideal clients, audience, and peers to bring EASE into their biz and life! Elephant Social


Amber Temerity

Don't let your eagerness to flee overwhelm your sensibilities. I get it, you're burnt out, but if you quit before you're financially safe enough to do so, you'll end up even more stressed and risk having to dive back into corporate to make ends meet; balance eager with logic, and make the leap when you know you're safe to be in the negative for a couple months without risking financial ruin.

Amber is a time management expert who helps online business owners get out from under the overwhelm and automate systems that allow them to find freedom through business. Thrifty Guardian


Shay Klomp Bueters

There is a reason for that inner voice quietly whispering in your ear to move in the direction of your dreams. You are meant to share your gift with the world!

Shay Klomp Bueters is passionate about helping people live healthier, happier lives by ”breaking –up with sugar” and finding foods that truly nourish the body. Contagiously Healthy


Erica Blair

Make use of Facebook groups. They are one of the best ways to conduct market research, get exposure, and find potential clients that exist online now. If you're not sure of a business idea, you can use Facebook groups to ask questions as part of your market research, test different routes, and actually connect with people who can serve as clients or collaborators down the road.

Branding & Marketing Strategist. Erica Live


Anna Lundberg

The number one reason why people fail to make the leap from a full-time job into starting their own business is that they’re not clear on what exactly it is they want to do. My advice is to really understand what you’re escaping to; i.e. what’s missing from your current job, what are you hoping to achieve with the change, and how does this fit in with other areas of your life (e.g. family and friends, travel, other interests…)? Once you know what it is you really want, then you can work out a plan as to how to get there: how much money you’ll have to save, where you’ll need support, and the steps you’re going to take in order to achieve your goal.

Anna S.E. Lundberg is a personal coach and business consultant. She has built a portfolio career in which she now coaches individuals through the transition from a full-time job to starting up on their own business.


Tina Dietz

Take a phased approach to give yourself more flexibility and stability when you're first exploring starting a new business. If you don't have experience as an entrepreneur, you're not just putting together and marketing products and services, you're going to go through an entire identity change and learning curves galore. Give yourself a series of experiments, and work with a qualified coach or mentor to shortcut your learning curve. When you're ready to step off fully, you'll feel it deeply and be much more prepared for long term success.

"Internationally acclaimed business coach, audiobook publisher, popular podcast host, launch specialist and bestselling author. Launch Your Audiobook


Fatema Karim

Take some time out to plan ahead. It is a big step, therefore, work on preparing your mindset. Also, start saving early.

Empowers online entrepreneurs to become high performers and scale in their business through teaching/consulting. Fatema is also an avid coffee drinker and loves to travel. Biz Empowered


Rob Cubbon

Start earning money while you're working by doing (freelance) work for clients in the evenings and weekends. Build a website and start creating content.

Rob Cubbon is an Amazon bestselling author, online teacher, graphic designer and ex-slacker who wants freedom for you and success for your business.


Jon Haver

The key to achieving the goal of leaving your day job and building a succesful online business really comes down to 3 things I believe...

First - You need to be crystal clear on WHY you want to leave the day job. Challenges will be faced and you have to have your reason crystal clear so that you can push through!

Second - Find a way to add value to a market, whether that is as a service or information or a product... whatever you do will only be successful if you are providing value to the marketplace.

Third - Grind through the work...work your face off and don't stop until you have achieved success! 

Jon is a huge geek when it to comes to automating and outsourcing any activity. He shares everything about building an online business that is hitting $20-$40k per month! Authority Website Income


Ryan Biddulph

 Follow your fun. Build a business that you genuinely enjoy building. What can you gab about all day long? Blog about it. This passionate, inspire, fun energy helps you circle the globe whether you have no savings or ample savings because you'll detach from outcomes and gradually build up steady income streams when you're focused on following your joy, creating and connecting versus worrying like hell about money.

I never got too caught up in planning. I followed my passion. Which is why most folks look at me like I'm from Mars when I tell them I live for months or years in places like Fiji, Bali, Thailand or Costa Rica, while running my blog.

Most folks obsess over tips or trips or techniques, following these ideas so they can give themselves permission to quit their job and circle the globe. I decided to hit the road. Happened to make some scratch before I left. Here I am, 6 years later, still circling the globe.

I didn't wait to travel.

I went.

Follow your joy guys!

This ain't a world of doings.

It's a world of beings.

Be your fun. Be your passion.

Build your business around that being.

Ryan Biddulph can help you retire to a life of island hopping through smart blogging at Blogging From Paradise.


Jessica (Tyner) Mehta

Just like having a baby, there's never a "perfect time" to quit your job and start a business. After all, 90 percent of startups fail, and in any other circumstance those aren't the kind of odds anyone would gamble on. Planning and saving can do a lot to get you prepared, but it likely will never make you feel certain. If possible, save at least six month's worth of living expenses. If necessary, get any certificates/licenses/etc. taken care of while you still have a stable income. Set a time frame that's reasonable yet challenging to go all in, and don't make it any farther out than 18 months. Within that time frame, force yourself to give it your all. It might seem like holding a part-time (or even full-time) "steady" job is a safety net, but it will quickly become an anchor. You can't give everything to owning your own business when you're still even partially relying on another job to keep you afloat. (The one exception? If you can turn a job into passive income).

Jessica founded MehtaFor, a writing services company, in 2012 which serves a variety of clients including Fortune 500 enterprises and major media outlets.


Catherine Wood

My advice for aspiring entrepreneurs is to decide what criteria is needed in order to give up your 9-to-5 (money saved, clients generated, products produced, etc.) and then make a firm commitment to yourself stating by when you will pursue it full-time. Don’t wait for the fear to "go away" because it never will. Do not be committed to needing to know all the answers before you get started because clarity comes from having already taken action, not from waiting. You’ll be able to start taking action when you give up the need to get it perfect; each failure brings you that much closer to your next success. So start before you’re ready, before you have the time or the money. By simply committing to pursue your dream and follow your passion, you will create the time and money, and you'll be amazed at how opportunity welcomes opportunity!

Founder and executive life coach of Unbounded Potential in Washington, DC.


Kristen Edens

Dreams and visions are what keep us focused but it takes more time, energy, and money than what we plan for to make it happen.

Content writing and development service for business. Services include content creation for websites, newsletters, blogs, social media profiles, and marketing copy. Kris also provides coaching on "social success" for quiet entrepreneurs. Kris the Scribbler


Lori Cheek

Entrepreneurship is being on a mission where nothing can stop you. It will take twice as long as you'd hoped, cost exceedingly more than you'd ever budgeted and will be more challenging than anything you'll ever try but if you give it your all and refuse to give up, you can trust it will be the ride of a lifetime. My advice to other aspiring entrepreneurs is to be brave and follow your instincts. You can't cheat the grind, but if you give it your all, you can trust that the payoff will be worth it.

Founder and CEO of Cheekd— a hyper-speed mobile dating app that makes missed connections obsolete. Lori, was recently listed as "The Digital Dating Disruptor" and "One of the Top 10 CEOs to Watch.”


Ana Hoffman

Don't quit until you get your feet wet with your new business. Might sound like a good idea to learn how to swim by jumping in with nothing to keep you afloat, but that doesn't work out well in most cases.

Start pulling a stable (doesn't have to be big!) income from the business, then consider diving all in.

Ana Hoffman is the founder of Traffic Generation Cafe, a blog that brings together the most profit-pulling free traffic generation tips, hacks, and resources.


Maureen Witten

Fail fast and learn to become resilient. It took me three expensive and painful years to get to where I am today, but I'm so glad I stuck it out! Once you get that first taste of success, you'll be hooked!

Emotional Eating Coach and Intuitive Eating Counselor. Maureen helps women stop eating their emotions so they can live a healthier, happier life. Be Yourself Wellness


Emma Drew

Try to build up some income before taking the leap. We are all busy people and it means putting in long hours, but you'll need to know that you can make money!

Emma Drew quit her full time job in 2015 and hasn't looked back since. She now spends her time helping others to make money online.


Benji Hyam

Create a business that you're passionate about and that you would do even if you didn't make any money. Reasoning: Most companies won't make money right from the start. Dealing with the mental frustration of working tons of hours for little to no pay is hard, especially if you don't love what you do. I would've given up many times already if I didn't love working on my business.

Co-Founder of Grow and Convert and Wordable. Previously ran marketing at two venture-backed startups in SF.


Pauline Paquin

One advice I would give budding entrepreneurs is to make sure you can afford it. The last thing you want is to have to abandon a project that needs a few more months before it takes off, because you can't pay rent. I would target at least 12 months worth of living expenses, so you don't end up flipping burgers at night after you work on your stuff. Downsizing to a smaller place and minimizing your spending can go a long way.

Pauline left the 9-5 at 29 to live life on her own terms. She is currently based out of sunny Guatemala. Reach Financial Independence


Dominic Wells

Start out learning and getting your business set up before you are ready to quit. You will of course get much more momentum and success once you go full-time, but if you can get past the learning curve before you quit your job, things will be much easier.

Building and selling done-for-you affiliate websites to save people time getting started. Human Proof Designs


Laura Pennington

Make use of all your non-job hours - wake up early, stay up late, and put in some hours on the weekend. It's much easier to scale your side business up this way so that you have the confidence to leave your job.

Laura Pennington left her job as a burned out inner city teacher to pursue her dream of freelance writing full-time. She's been working for herself since 2013. Six-Figure Writing Secrets


Crystal Johnson

Make sure you have something that people actually want or need; talk to your potential clients, know who they are, and understand the problems you will solve for them.

In other words, validate your business idea by speaking with the very people who will buy from you.

Through this validation process understand how you can differentiate your business so you stand out from your competitors.

Ask questions like,

"What frustrates my potential customer about what my competitors currently offer?"

"What needs are my competitors not filling for my potential customers?"

"What keeps my potential clients up at night?".

Research the Red Ocean, Blue Ocean Strategy to help you through this process and get crystal clear on this!

Crystal Dawn Johnson is a sales & business coach who helps online service businesses attract ideal clients so that they can have the freedom and income they desire outside of a 9-5.


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Comments

  1. Eli Seekins says

    December 19, 2016 at 9:21 pm

    Great post Neil!

    I’m super passionate about this topic. Everyone’s entrepreneurial journey is different. There are so many different paths you can take.

    Glad to be a part of this.

    Reply
    • Neil says

      December 20, 2016 at 8:24 pm

      Cheers Eli, I love this stuff too, which I’m sure you can now tell 🙂

      Reply
  2. Ryan Biddulph says

    December 20, 2016 at 7:56 pm

    Hi Neil,

    Thanks for sharing my thoughts among these pros 🙂

    Following your fun is a critical component of any venture. Because when you face resistance, you will either do the fun, freeing thing or surrender to your fear. Can’t have it both ways. If you follow your fun, you will do the fun, freeing and at times scary things that help you leave your 9-5 behind to build a thriving business venture.

    Ryan
    Ryan Biddulph recently posted…10 Tips to Detach from Anchor Like Blogging OutcomesMy Profile

    Reply
    • Neil says

      December 20, 2016 at 8:31 pm

      Totally agree Ryan, “following your fun” is why I’ve stopped previous businesses and is why I’ve got this far with my current business. This reminds me of something I read recently, “start a business you’re willing to help people for free”. That’s not to say you should offer free services, but it’s a good way to test your passion.

      Reply
  3. Isaly Holland says

    December 24, 2016 at 7:28 am

    This is an amazing post! I love hearing other peoples thoughts on raking such a big leap in life.

    xoxo
    Isaly Holland

    Reply

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