Live an adventurous life by combining work + travel

Becoming self employed: How I ditched the 9-5

Becoming self employed: How I ditched the 9-5

At 23, I had no clue what I wanted to do with my life.

It was October 2011, and I was working as an office receptionist. Having already gone through numerous jobs in retail, customer service, administration, and printing, I could never find anything that stuck.

Every time I started a new job, I’d start hating it a few months in. This reception job was no exception. I would sit under fluorescent bulbs for 8 hours every day, answering the phone when it irritatingly rang every 5 minutes, placing letters into envelopes, and dealing with office politics in a job where age discrimination as prominent as segregation in the 50s.

But what else could I do? If I got another job, surely the same cycle would just happen over and over again.

Who would have thought that it would be something as simple as receiving an office delivery that would change my path from detesting every job I had to working for myself.

This is the story of how I took control of my career.


finding an idea

My first business idea presented itself when a box of wedding invitations were delivered for my colleague. She rushed out of her cushy office to open the package in front of me, and her face fell. She’d had the invitations made professionally, but the design was plain and boring.

Having studied Graphic Design, I thought hey, I could give wedding invitations a try! So I started creating some designs, had samples printed, listed them on Etsy, and waited for excited brides to start throwing their money at me.

But all I heard was crickets. No one was interested in my invitations, and after a few months I realised that the market I was designing for was very small. Sure, there are couples who want their stationery professionally designed, but most people also want to take part in creating it. In other words, I was offering a product that wasn’t a good match for the modern couple.

I felt deflated and spent a few months brooding, but then had the idea to try out some of my invitation designs as DIY printables. I would do the design and text layout, then give instructions for the couple to print it themselves.

My Etsy Shop

One of the designs in my Etsy shop.

This idea took off very quickly – I had my first sale within a month or two, so from then on I’d get inspiration from Pinterest, magazines, and wedding blogs to create new DIY printable stationery designs to add my shop.

After a year of selling my DIY designs online and getting to the point where I was making a few hundred dollars every month, I realised I needed to do something else. If I wanted to quit my full-time job, my Etsy shop alone was not making enough money for me to live off.

So my next idea was to try my hand at blogging. I thought I’d create an online space with useful information on weddings, and direct traffic from the blog to my Etsy shop. I purchased an e-course from lifestyle blog A Beautiful Mess and spent a few weeks completing the lessons to get my blog started.

I saw a slight increase in sales but unfortunately not much of it was coming from my new blog. The increase had come from the additional time and effort I’d put into maintaining my shop, creating new products, improving my photography, and using Pinterest to market my products.

I also struggled to make my blog stand out. The wedding industry is a saturated market. With professional photographers contributing to many fantastic wedding blogs, my little one-woman band didn’t really stand a chance.

Screenshot PS blog

My Polkadot Stationery blog.

After 4 or 5 months, I considered starting a second blog. It was just before a trip Robert and I took to Bali and I was skeptical about once again sharing my photos on Facebook. I realised that I had so much more to offer than a few quickly forgotten photos, so I went about registering a domain name, designing a logo, and frantically posting content on my new travel blog.

This was actually a risky commitment, as the travel blog didn’t have any connection to my Etsy shop, so I’d basically be starting a second business from scratch. My Etsy shop would also grow less quickly as I’d have to put my time into blogging instead.

Still, I was really excited about it and had high hopes that I could make blogging a second stream of income. If I had two businesses each making a small amount of money, I might finally be able to make enough to live off.

Yellowstone National Park

My trip to Yellowstone, USA, a month before I opened my Etsy shop in 2011.

Taking the leap

It’s not easy to know when you’re ready to take the leap and leave the security of your full-time job. Do it too early, and you’re doomed to fail by running out of money and resources. Leave it too long, and your business may never get enough of your attention to get off the ground.

I worked for 2 full years after opening my Etsy shop before I made the tough decision to quit my job. I was nervous, but confident that I would try my best to make it work.

I’d saved up enough money to live off for 6 months, though I knew that my savings would actually last longer than that as I was still making a little money through Etsy. I also got a part-time job at a print shop (1-2 days per week) to help cover my expenses.

After a few months, I finally started to see the benefits of putting all this extra time into my businesses. My Etsy sales more than doubled since the year before, and this blog is quickly growing into something that I can monetise.

If I hadn’t left my full-time job, I wouldn’t have been able to grow both my Etsy business and my travel blog nearly as much as I’ve been able to. Becoming self-employed was also a huge deal for my move to New York, as I had an income that wasn’t dependent on my location.

AGWT in New York City

Me after I moved to New York City, 2015

Responding to change

At the beginning of 2015, I realised that continuing to post on my stationery blog was futile. I didn’t have enough time for it and had lost all of my original enthusiasm now that I’d produced a rapidly growing travel blog. I made the decision to stop posting.

I wanted to somehow merge my new travel blog and my Etsy shop, so I started designing printable travel stationery such as travel journals, art prints, and trip maps, and attempted to direct traffic from my travel blog to my shop.

It’s been reasonably successful, and I’ve been able to get feedback on other travel related products that I can sell in the future.

Work and travel at the same time

These days, I’m able to work and travel at the same time

My tips for becoming self employed

  1. Find a killer idea. The entrepreneurial type is always on the hunt, looking for problems and thinking of ways in which we can solve them. It could be starting a blog, creating an app, or selling an online product. Sometimes the ideas are unachievable and sometimes they’re entirely possible, but the point is that we’re brainstorming until we find something that might work.
  2. Think about the skills and passions you currently have. I have skills in design so I used them to start a business designing stationery, and I’m passionate about travel so I used this as a base for my blog. I had zero blogging skills, but I came to learn them throughout the process of starting two blogs. Remember, the most important skill you have is the ability to learn.
  3. Implement your ideas. Figure out what steps you will need to make it work. If you want your idea to support your lifestyle eventually, you’ll need to think about how it can be monetized.
  4. Start saving money like crazy. Be prepared for no income for a long while. Overnight success is very rare, for most people it takes 1-3 years (sometimes more) to set up a profitable business.
  5. Have a plan before you take the leap. Make sure you can cover your expenses and give yourself a generous amount of time to get started. It’s easy to be optimistic about your plans but in reality, it might take longer than you think.
  6. Notice when things need to be changed. An essential part of being an entrepreneur is knowing how to respond to change, or changing things when something isn’t working. There’s no point wasting your time on a dying project (such as I did with my stationery blog) when you could be doing something more productive.
  7. Trial and error. Sometimes, a business idea that you thought would work will flop. I realised that with both my original wedding invitations idea and my stationery blog. But with a little trial and error, I was able to tweak my ideas to find something that works for me.

I’ve learnt a lot of things from becoming self employed, and can confidently say that it’s the most rewarding thing I’ve ever done. It hasn’t been an easy journey and it’s nowhere near completed, but I’ve never been afraid of a little hard work.


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Ashlea Wheeler

This post was written by Ashlea, a colourfully clothed and excitable vegetarian who loves photography and exploring the world. Find out more about me.

56 Responses to “Becoming self employed: How I ditched the 9-5”

  1. Marie @ Marie Away

    I feel like I am where you were in 2011, and kind of unsure where to go from here. Thank you for sharing this, it really inspires me to take control of my own career path. 🙂

    Reply
    • Ashlea Wheeler

      I hope I’ve been able to give you an insight into where to go from here! It’s a really tough decision to make, but if you try and fail there’s no harm done. Best of luck starting your own career Marie 😀

      Reply
  2. Marc

    Ashlea, this is a great article! It was inspiring to read how you have found your way and became self-employed! Both thumbs up!
    Cheers from Germany
    Marc

    Reply
    • Ashlea Wheeler

      Thanks Marc! I had some people asking about how I became self employed, and I realised I’ve never really put the whole story into words before, so here it is 😀

      Reply
  3. Eden

    This is such a wonderful and inspiring post! I feel like I was you before working the receptionist job. I just finished graduating University and all I could find was a receptionist position and yes, age discrimination is huge. It wasn’t until last year I decided to quit my job and get my Masters degree. Now I want to start my own business. Thanks for sharing your tips!

    http://www.mintnotion.com

    Reply
    • Ashlea Wheeler

      I’m so glad you enjoyed it Eden! We all like to think that discrimination is no more, but age (and gender) discrimination is so prevalent in today’s society. I always felt like I was looked down upon for being so young, and being female didn’t help either. It’s as if young women in the workforce are only good for filing papers and addressing envelopes, and every time I spoke up about it I’d get told that I should just deal with it. To hell with that!

      Good on you for continuing your studies and aspiring to start your own business, I’m sure you’ll be successful 🙂

      Reply
  4. Lizzie

    I love reading other people’s stories about how they came to be freelance and yours is so interesting! I love your designs and I think they work perfectly alongside the blog.

    It’s definitely about knowing when the right time is to quit your job. I’d been wanting to go freelance for a year or so before I actually did, but instead I kept hopping from one job to the next because I thought it would be safer. It got to the stage where I thought ‘going freelance’ was just a dream that I might be able to do 10 years down the line, but then my boyfriend got offered a job in Spain and, well, I took the plunge. It’s hella scary to start with, but I’m so, so glad I did it.

    If you’ve got the right mind set there’s money to be made everywhere! I love being self-employed – definitely the most rewarding decision I’ve ever made, too 🙂

    Reply
    • Ashlea Wheeler

      Thank you so much Lizzie! It’s great to hear that you like my designs 😀

      I think that’s the hardest thing about becoming self employed, knowing that you’ll be leaving that safe place of having a steady job. It’s a scary prospect! And I don’t think it gets any less scary, you just get used to the idea after a while. I’m so glad you were able to pluck up the courage, well done!

      Reply
  5. Mikaela Swedlund

    Thank you for this post, it was very encouraging. I am wrapping up two years of teaching in Korea and am in the process of figuring out what is next. I have also had numerous jobs in the past that made me cringe, and I don’t want to go back to that.
    It is such a scary thing, to live without the “normal” ties. But that is what I want. Thanks you for the great advice!

    Reply
    • Ashlea Wheeler

      It’s definitely scary not having a steady income, but it’s also invigorating. Knowing that you’ve been able to do what you want without having to rely on someone else is an amazing feeling. I hope it all goes well for you Mikaela!

      Reply
  6. Renuka

    Great ideas and tips! Even I was contemplating on starting my own business, but I am still not sure what that would be. But I guess, as you said, there is no harm in brainstorming. You never know what may work! Thanks!

    Reply
    • Ashlea Wheeler

      I think the key is to know that you’re ready to start a new project, and just keep your eyes open for something to come up. It’s amazing how many opportunities we skip over every day. Good luck with finding an idea Renuka!

      Reply
  7. Mariel

    I’ve always felt like my purpose/destiny/whatever-ya-wanna-call-it lies off the beaten path. Compared to the rest of my peers, I’m not all that “successful” (I don’t have a 9-5 at which I’m climbing the corporate ladder and am not entirely sure where I’m going), but my entrepreneurial spirit is strong and the conventional life/career isn’t something I’m willing to settle for. Anyways, I find your story entirely relatable to my life! I enjoyed reading about the path you took to get to where you are now 🙂

    Reply
    • Ashlea Wheeler

      Thanks Mariel, it sounds like you and I are very like-minded! I think success should be defined with what makes you happy rather than what other people say it is. For example, my success is certainly not that I’ve made lots of money (which I haven’t, I’m quite broke haha) but that I’ve been able to create something that I’m passionate about and that’s growing and developing every day. To me, that means I’ve succeeded in what I set out to do 🙂

      Reply
  8. Maria

    I can see part of myself in the story. I’m 23, I recently quit my job because it was draining my energy out and I didn’t enjoy it no more… Starting my travel blog and developing it was my N1 passion. I have no 9-5 job for 2 months now and I’m still trying to figure out what am I going to do with my life, what should I do to make a living, because earning enough from a blog isn’t quite realistic… I’m happy to hear you found out what you want to do, I will continue to search myself and my place on the world and on the market but your story is truly inspirational! Keep up the great work!
    – All the best, Maria

    Reply
    • Ashlea Wheeler

      Earning enough from a blog is totally realistic if you want it to be! It might take time, but if you continue to put hard work and passion into it then it will eventually develop into something that can support you. It’s nice to have a side income while you make that happen though, we all gotta make money somehow 😉 Thanks for sharing your story Maria!

      Reply
  9. Jessie Broad

    Oooh you are so inspiring! I am working hard to try get my blog more awesome and into freelance writing so that I can work and travel, I love reading about peoples success stories. It helps me know that what I’m doing is on the right path, that what I want to do is possible! So thank you for this post, I know it helps a lot of people including myself!

    Reply
    • Ashlea Wheeler

      As long as you’re willing to put in a little time and effort, anything is possible! I’m sure you’ll make it Jessie, keep trying and you will get there eventually 😀

      Reply
    • Ashlea Wheeler

      Thanks Sher! Looks like you’ve found a really interesting way of travelling and making money on the road. What is the product that you sell at the markets?

      Reply
  10. Nikki

    Great post! I recently have gone full time freelance to be a travel journalist and it is definitely both freeing and stressful as I learn to make dollars stretch, am constantly hitting the ground running to find paying assignments while also maintaining my blog, http://www.thepinthemapproject.com. I actually just picked up a temporary office job to accrue some more money in savings before traveling for a month to Europe this summer. At the end of the day it really is about passion and drive to make your dreams a reality.

    Cheers!

    Nikki
    http://www.thepinthemapproject.com

    Reply
    • Ashlea Wheeler

      You’re absolutely right Nikki! Freelancing is both freeing and stressful, it’s a whole different experience from working the 9-5. But it pays off big time if you can keep at it long enough. I love your story, just read your post on things to consider before going freelance and it sounds like you and I are at a very similar stage of our self-employment! Keep in touch and let me know how it’s all going for you down the track 🙂

      Reply
  11. Camila

    Blogging and reading about the stories of amazingly inspirational and yet relatable woman like you has really inspired me. I’ve been thinking for months and then came to the conclusion – I’m not an entrepreneur, I will never have a business idea, but what I have is my writing and my 3 degrees in comms and literature and I would like to get into freelance content writer!

    Reply
    • Ashlea Wheeler

      I’m really glad you were inspired by my story Camila 😀 I would never say never, as sometimes these ideas can pop up out of the blue, but becoming a freelancer can be just as invigorating!

      Reply
  12. Diana Southern

    So great to read an inspirational story like yours, Ashlea. I can’t believe how many people I know who put up with a job they hate without doing anything about it. I was a serial job hater, too, before I quit in March 2014, and the toughest thing for me was to convince myself that I could figure out a way to make it work. You’re so right about trial and error being a totally normal part of entrepreneurship. We just have to keep at it to find out what works best. 🙂

    About a year after quitting my job, I may be far from a fairytale ending, but I am SO HAPPY now that I’m calling all the shots. I no longer dread the day when I wake up in the morning!

    Good luck with the blog and your Etsy shop. Love reading your posts!

    Reply
    • Ashlea Wheeler

      Thanks Diana! It’s great that you were able to take the leap too. It’s easy to feel like giving up when something doesn’t seem to be working, but we’ve just got to keep trying until we find something that does. I know exactly what you mean about not dreading the day now that you’re calling the shots! It’s so wonderful when ‘work’ is something we actually care about 😀

      Reply
    • Ashlea Wheeler

      Thanks Carly! You should stop wishing and start doing – no need to be a graphic designer or blogger to be self employed, you can do almost anything as a freelancer!

      Reply
  13. Karen

    this is so inspiring to me! I’m 23 and a recent college grad, and I don’t want to have a 9-5 forever – I would love to travel and work on blogging as well! I’m still figuring out what I like and trying to make my passions a reality 🙂

    Reply
  14. Tiffany

    Thanks for sharing your story! Very interesting! One day I want to quit my job as well to travel. Have to pay off the student loans first!

    Reply
  15. Nico Vermeulen

    Thanks for sharing your story and these tips with us! I’m about ready to take a big leap of faith into full time photography and blogging. I’m really looking forward to spend more time just learning how to improve my skills and see my passion grow! Thanks for being a kind of inspiration 🙂 I’m keeping your tips in mind!

    Reply
    • Ashlea Wheeler

      Not a problem Nico, I knew that some of my readers were interested in hearing my story 🙂 You won’t believe how much your skills will grow once you have some time on your hands! It’s amazing how much your creativity develops once you get rid of other distractions. Best of luck taking the leap 😀

      Reply
  16. Sophie

    I found you randomly through bloglovin. I am just starting out on this creative journey of a blog. But I don’t feel like I have a killer creative idea. I write a little bit about makeup, positivity, and writing. Although I hope that in the future, I could make some money from the blog, I started it mostly to make friends. But even that is tough because I’m not completely one thing or another. Thanks for sharing about your journey.

    Reply
    • Ashlea Wheeler

      Thanks for your comment Sophie. It’s hard to find a particular direction to follow when you’re first starting out, but I wouldn’t worry about it too much. As you get better at blogging and start realising what your readers want to hear more about, it gets easier to figure out. Keep at it and I’m sure you’ll find your way! 🙂

      Reply
  17. Katie Featherstone

    Thanks Ashlea. I’m 23 right now and know exactly how you felt back then… I’m hoping things go the same way for me as they did for you, but for now I will have to focus on actually finding a 9-5 to quit. haha! Thanks for the inspiration. Etsy is a good shout!

    Reply
    • Ashlea Wheeler

      Don’t worry about finding a 9-5 if it’s not for you! Well, I suppose you’ll have to make decisions as they come, but the biggest regret for me was that I let it go on for so long before actually getting started on making a change!

      Reply
  18. Karen

    I loved this article! I’m 23 now (about to turn 24) and I can definitely relate. I would LOVE to do travel blogging or other freelance work with blogging as a central part of it, but unfortunately I don’t have any training in things like graphic design or web design to help me work remotely. I haven’t given up and I’m still thinking of options!

    Reply
    • Ashlea Wheeler

      I’m glad you can relate, Karen! It’s never too late to start learning, if you’re interested in any sort of job that would allow you to be location independent (such as Graphic Design) there are plenty of courses, some of them online, that you could take to start building up your skills. Give a few things a try and see what appeals to you 🙂

      Reply
  19. Wendy

    Hi Ashlea,

    Just found your blog through Bloglovin. Congrats on your journey so far, I look forward to seeing more! My husband is a photographer and has been an entrepreneur since 2004. I joined him in 2011 but we really weren’t prepared enough for it, so I feel like the advice of working to save up to quit your job, and also having a plan for your new business is so vital and something people really need to think about. We’re launching our new dream business next month. We’ve been planning for over a year and working to save up money. It’s still going to be scary when I quit my job but I’m so ready for it! Have a great week 🙂

    Reply
    • Ashlea Wheeler

      Thanks Wendy! You’re absolutely right, knowing when to take the leap is very difficult and if you’re not fully prepared, then it may not work out. Planning and saving are the keys to success! Best of luck with your new business launch! It will be scary but it sounds like you’re fairly prepared, so all you can do from here is give it your best shot 🙂

      Reply
  20. bethan

    I’ve just read a few or your articles and you sound like an amazing person with an amazing life! I’m only 16 but I’ve always wanted to travel and have had this craving to explore the world for a few years now. Recently, I have realised how repetitive and structured life can be – you are expected to go to school, then college, then university and then have a job and a family and so on…and that doesn’t sound like the life I want. I’m still not sure on what job I will have but something to do with art i think, however, thankyou for sharing your journey so far and all the tips for travelling, because I intend to explore the world and break free from peoples expectations of how I should stay in line.

    Thankyou again for the motivation,
    Bethan

    Reply
    • Ashlea Wheeler

      Thanks for your comment, Bethan! I’m so glad you’ve realised that life doesn’t have to follow a standard path, and that there’s so much more to it than just being a face in the crowd. Travel can be a fantastic way of enriching your life, and your passion for art should be a great skill to base your career on. Best of luck creating an exciting life for yourself 🙂

      Reply
  21. Nama

    I cant even begin to say how thankful I am for reading this article.Iv been working in an architectural firm for 2years and honestly hated it.I am currently struggling to find work and like you scared to fall into same monotonous habbits in a new working enviroment.Im starting to think this is all gods way of telling me to take that leap and start own thing where Ill feel more fufilled and motivated.I have Always had this innate passion for design and after reading this article I am more employed than ever to reignite the passion to start my own business where i get to do what I love which is design.Ashlea I dont think its a coincedencs that you landed on my pinterest feed at 4am especially when my life is at such a crossroads.Thanks again for this article I almost cried as I could relate soo much.Regards Nama

    Reply
    • Ashlea Wheeler

      Thanks for your wonderful comment, Nama! It’s so great that you’ve been able to see the path that would make you happy in life. All you have to do is make a plan, and start taking steps to make it happen 🙂 Lucky for you, design is a great skill to have for self-employment as it’s in demand, and can be completed from anywhere. Best of luck with your positive life changes!

      Reply
  22. Karolin

    Ashlea,

    This is an amazing article ! One that I can actually relate to. I am now on my late 20’s though and just like yourself I’ve been through customer service, receptionist , retail and even health insurance. I have two children and I’m tired of working for someone else on a 9 to 5 basis . I am currently in the process of reinventing myself and hoping to find something that I can actually enjoy life and my children and earn money that I can live of. I’m definitely going to keep you tips in mind!

    Thank you,

    Karolin

    Reply
    • Ashlea Wheeler

      Thank you! I’m so glad you can relate – reinventing yourself can be scary and challenging, but if you have the drive, then you can achieve anything. If you manage to create a more enjoyable life for yourself and your children, then it will all be worth it! Good luck, Karolin!

      Reply
  23. Elizabeth

    Wow! This really spoke to me. I am 23 and work as a receptionist in an office and hate my job more and more every day, but don’t see the point in quitting because I will keep doing the same thing over and over. So yeah, the first lines of this blogpost kinda stopped me in my tracks haha!

    You’ve inspired me to start looking into creating a blog and maybe an Etsy shop.

    Thank you 🙂

    Reply
    • Ashlea Wheeler

      I’m so glad you enjoyed the post, Elizabeth! I can definitely relate to that feeling of being in a job that’s unenjoyable and mundane. Getting creative is a great outlet and can absolutely make you some money, though it might take a while – so make sure whatever choices you make will be financially smart as well 🙂

      Reply
  24. Kelan Kline

    Awesome article!

    My goal for 2017 is become 100% self employed! We started our blog in August 2016 and continue to see growth which is exciting. I also went back and got my NYS Home Inspection License. I have been an entrepreneur trapped in the 9-5 since leaving college almost 5 years ago.

    My wife has a solid job as a NYS teacher with benefits and a pension so making the leap won’t be that difficult of a decision. It actually might happen sooner than we thought.

    Your article got me jacked up and high on life! Stories like these have a HUGE impact on others, more than you know. I can’t wait to be able to share my story similar to yours.

    God bless and keep up the amazing work!

    Follow us on Facebook, we would love to do the same.

    – The Savvy Couple

    Reply
    • Ashlea Wheeler

      Thank you Kelan! Taking the leap to becoming self-employed not an easy decision, and it can be quite intimidating to follow through, but you will not regret it! Self-employment is truly awesome. I really hope your plans work out and that you achieve your goal of becoming self-employed this year 🙂

      Reply

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