The Toughest Lessons I Learned When I Became Self Employed
March 8, 2012 in Turning Your Dream Into Reality
One of my favourite missions in life (yes, I have many, I’m a scatterbrain like that) is to help every single person I meet (whether face to face or virtually) live the life they want. Broad mission I know, but I usually start with career. “What is your passion and why aren’t you using it to make money?” is my initial question. Fear, more often than not, is the answer.
Fair enough, having the pressure of making all the decisions about the business, not knowing whether you’ll make any money at all that week, feeling like a failure – it’s all terrifying. Most things that seem amazing are terrifying though, hence why most people stick to the safe option and stay as an employee.
There are many benefits to being self-employed. I choose my own hours. I can choose my own clients. I don’t have to worry about a boss not letting me take sick leave or holidays. BUT amongst all the “Yay, I’ll take the morning off to see a movie” frivolity, there have been some difficult (and often terrifying) realisations.
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Great opportunities don’t simply come to you.
I actively started advertising for my teaching services about a month before I resigned, which meant that I already had a small handful of students before my regular pay check fizzled out. As much as I wanted to have faith in word of mouth spreading the news of my greatness like wildfire, I kept my advertising up for almost an entire year. Just as well – I only became fully booked late last month.
You may know how talented you are (and your mum might too) but that doesn’t mean that potential clients will find out about you through the grapevine. Don’t rely on your reputation being built for you, you need to build it yourself. Get out there and pimp/network your butt off! Take a squiz at my post on self promotion if this idea freaks you out.
Aim to send 2-3 emails (or make as many phone calls) every day to people about your services. SHOW them what you’re capable of. Yes, you may have to do a little work for next-to-nothing (or literally nothing) to get your foot in the door, but if this is a company you really want to work with – do it. Don’t get sucked into the “creatives work for free” trap though – decide if this is an important contact to have that will lead to future projects, or not worth your time.
You have to work hard to build your brand and reputation in the marketplace, so remember to schedule a serious chunk of time each day to getting your name out there, particularly in those first 12 months. You’ll thank your past self later down the track.
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Passion doesn’t pay the bills.
This one is a very sad but very true statement and one I wish was a lie. It made me sad just typing it! Just because you have a burning fire of enthusiasm inside of you, doesn’t necessarily mean that what you love to do will be successful financially. I lost thousands of dollars on my first business venture a few years ago and was just lucky that I’d decided to keep my 9 – 5 Â job that time around.
When I first quite my “day job” I decided to hang onto my casual weekend work initially just to have the peace of mind that at least rent would be paid every month. I was willing to risk a lot of things but the roof over my head was not one of them. Make sure you have savings or a little income trickling in to keep your stress levels from shooting through the roof.
Think carefully about how you are going to profit from your venture. We creatives tend to snort at the word profit (because we’re über cool and don’t want to be greedy), but darling – you gotta live and you deserve to be successful! The way I went about things was to have ideas for a few different revenue streams – at the moment I teach singing, I sell an eBook (on this very topic) and manage social media for brands. I love the variety and the security that three income streams provides.
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Rejection comes to visit (and overstays his welcome). Often.
Yes, you will have people who don’t like your style, your product, your service or the way you wear your scarf. Everyone says “try not to take it personally” but you do. Every time. This is completely normal and I would tell you it gets easier – but it doesn’t, not really. You will always feel defensive about what you do, especially if it’s creative, because it’s a part of you. It’s something unique that you came up with and it has pieces of you all the way through it.
What you do need to do is come to terms with the fact that your product/service is not for everyone. Some people (your target market) will go gaga over it and that’s amazing! You don’t need everyone and their twin sister to buy seven of them each, you just need your little group of fans to adore it and tell their like-minded friends about you.
Take rejection graciously – you never know what bridge you may want to cross later on, and you don’t want to wander over and find that you burned it six months ago. Always ask for constructive feedback whenever you receive a rejection – there may be something you’re not seeing that could be altered slightly to appeal more to your target market. Find out why they passed you up and what you could change to have a better shot later down the track. Learn from these hurdles folks!
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Are you looking to venture into self employment?
Do you have any questions you like to ask or fears you’d like to voice?




Love this post Kimberly. I would love to quit my day job, but you nailed it, I am incredibly scared about giving up the security of a regular pay check! Your reality checks are noted – thank you for keeping it real xx
Thanks for this, Kim! It’s just what I needed to start off my day (the fourth one as a self-employed girl!). Thank you!
You are so welcome lovely, I hope some of it helped. Always hear whenever you need – hope it’s going well! x
Kim you star.
There’s nothing like having someone who’s actually done all this to have for advice. I’m trying to balance the incredibly scared/living the dream/making a living thing.. It’s tough, but I know that it’s all worth it in the end.
No matter how we each go about it, we’ll all have a story to tell, and we will have learned things one way or another.
You always seem to nail the timing with your posts,
Thanks once again for the inspiration!!
xx
Aww thanks lovely. I hope that I can help guide people like yourself that are just starting out and assist in any way I can! It can definitely take a little time to get things going, but I can tell that success will hit you fairly promptly – you’re a superstar designer! Glad you enjoyed the post – thank you for the sweet feedback. xx
Thanks so much for this post! As I am consciously working to become self employed, I love reading posts like this.
Hi Hannah, you’re very welcome. I hope it came at a good time for you! If you have any questions regarding self-employment and the road to get there, please feel free to ask! x
This post is just plain awesome! Not only am I bookmarking all your tips for when I AM self employed, but I think in a subconscious way, you’re hurrying up the entrepreneur inside of me :) Thanks lady
Thanks for your beautiful comment Tara! Apologies for spurring on your inner entrepreneur – there’s plenty of time! ;) xx
Great post! I have officially been self employed for a few months and love it. Though I very much relate to your first photo!
Thanks so much Blaze, I’m glad you enjoyed it. Haha, I think the first photo represents those first few months perfectly. How is it all going? x
Hit the nail on the head as always! I love what you said about keeping a few streams of income, that’s what I’m currently working towards creating for myself. I’d love to know more about the social media work you do? Did you train for it etc or stumble into it? It’s something that really interests me, too! Thanks again for being so darn inspiring x
Hi Amy, thanks so much! I just find that there’s a little more security with multiple income streams. It’s not for everyone, but is definitely the way I want to keep working.
Great question re the social media work. I was nudged into it by a friend of mine who was unable to take a social media freelance gig and recommended me for it. Before that I had a little experience through fashion writing with brand social media, but not a lot. I have learned a lot about the online world through blogging for years and being on most social media channels and it was a fairly easy transition into brand management. I think I have an advantage being a blogger because I know how other bloggers want to be approached by brands (I have felt their frustration after receiving PR pitch after PR pitch not addressing the blogger by name or offering anything of value to them or their blog). One of my clients I approached directly as I could see they needed some help and I loved their brand a lot, but the others have just started coming out of the woodwork really. If you have any specific questions, please feel free to flick me an email at kim(at)dreamdelightinspire.com. xx
Hey RockStar!
LOVE this post as it brought me back to when I first started my consulting firm with $200. I had a bad boss that set out to destroy my career and I thought I had more to offer life so I quit and started my business and never looked back. You’d think people would be encouraging and want to help out a young fella in Business but I had a long way to earn the respect of my industry.
Sometimes you need to work hard in what you believe in and the world will come around to you.
I disagree with you about passion not making you money. Passion will make you money but only if you’ve set yourself up in a way that it can. That means having a clear path to generate leads through your passion and then a strong conversion process to turn them into sales.
It’s all part of the journey and I enjoying seeing yours unfold from the stories you share on Twitter.
Congrats on your success Kim! Keep living the dream.
Dream, Build, Inspire, Lead!
AJ~
Hi AJ, thanks for your amazing feedback. It is always very tough when you’re starting out for your industry to start taking you seriously. but it seems like you’re making your dream come true. Awesome!
Perhaps I should have said “passion alone won’t make you money”. Combined with a good business plan, product/service and hard work it definitely can, you’re right.
Thanks for your lovely words, means a lot. :)
You’re so right. You’re so right. You’re so right.
I love how you spoke the truth, but always with a positive spin. So many people talk up self-employment like it’s so easy, and other talk like it’s too hard. This was really balanced.
Bookmarked!!
You’re lovely Hannah, thank you for your sweet comment. It’s definitely tough starting out but it gets a little easier every day because you learn things so quickly. Glad I’m sending a balanced message! xx
This was great! I’ve been very inspired lately to start my own career, be my own boss. As I’m still at uni i’ve got some time to plane it all, and sort it all out, plus i’ve got myself a part time retail job that can pay the bills.
Thanks again for this.
thecollectiveedit.blogspot.com
Thank you Chalsie! Sounds like you’re in a great position to start some really exciting future plans. It’s wonderful that you already know what you’d like to be doing. :)
Good stuff Kim! I would hate to do something just for the money, which is why I’m constantly trying to do things for fun before the money becomes a focus. I started Financial Samurai almost 3 years ago for fun, with the anticipation it could provide some income. Then I started Yakezie.com 1.5 years ago for fun, with no income expectations just to have a home base for the Network.
Fast forward today, I think I’ll give my fun a shot, and then create something new for fun so that in a couple years, maybe that too will be worthwhile!
Best,
Sam
Hi Sam, thanks so much for stopping by and leaving a comment. It’s always best to do things that bring you happiness for as long as you can, I’m so glad to hear you’re able to do that at the moment. I’m impressed that you’ve got two sites up and running. What will be your next new, fun project?
Hi Kimberley,
My next project is taking the leap of faith and publishing my book, How To Engineer Your Layoff: Make a Small Fortune By Saying Goodbye!
People don’t realize how profitable it can be to engineer your own layoff and walk away with thousands, if not hundreds of thousands of dollars if done right.
I want to encourage people never to quit, but get laid off instead. Employee rights are more powerful that we all know!
Best,
Sam
Love this post Kim, it’s so honest. I’m just starting out on my own too and the self promotion is the worst for me. I can handle the hard work and love it, but I’m still struggling with the building new business part.
It’s tricky isn’t it Christina? Getting the word out there in the big wide world is always a struggle. Thank goodness for the power of the Internet these days, huh? Thanks so much for adding your comment lovely! x
Thank you so much for this post! I read it at the perfect time- I am going through the same sort of thing at the moment. I thought I was fairly highly motivated and disciplined before I started my business; turns out self employment takes the meaning of those things to a whole other level! I am struggling with self promotion, and I think once I get over my fears of not being good enough/not wanting to big note myself, my business can move forward. I have written a post about this subject on my own blog: http://veneciadesigns.com/the-epiphany/
Thanks again, will definitely be making Dream, Delight, Inspire a regular read from now on!
Renae xx
Hi Renae, thank you so much for stopping by and sharing your perspective! Being self employed definitely takes a lot of discipline, more than I ever imagined. You’ll always struggle with “not being good enough” but it’s moving past that and doing something anyway that helps move a business forward. There will always be people that DO think your work is good enough. Thank you for mentioning my blog in your post, I am so excited to read about how your business develops with your new-found motivation! xx
Kim, thanks for sharing your archives on twitter, otherwise I wouldn’t have found this post! So true and so scary for me right now, as I’m in the process of building a career out of my passion. Scared sh*tless that I don’t have what it takes. Time will tell.
Thank you for your wise words, beautiful lady! xx