6 things I learned in my first year after quitting my job & freelancing full-time

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It’s been almost a year now since I made the somewhat nerve-racking decision to quit my full-time job without having a new one to go to.

I had been working in different marketing roles for over 7 years. I really enjoy marketing but I had reached a point in my career where I felt like it’s time to change direction a little bit.

I was (relatively) financially secure and decided now is the time to experiment and try a few different things.

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So I started to take on odd jobs and projects – some several days per week over a few weeks and others just one off projects. Anything from copy writing, managing events, market research and marketing automation projects to managing Google AdWords accounts and everything in between.

What was suppose to be a short-term thing until I find the next full-time gig has now turned into a longer-term situation. Mostly because it works really well for me. I love the diversity of the work I do and people I work with. I love the independence of being a freelancer.

While it’s been a fun and really interesting year, it’s also been a year of learning.

Being a freelancer sounds great – things like flexibility, independence, being my own boss and interesting work come to mind.

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But, in the last year I’ve learned how quickly FREE-lancer can turn into STRESS-lancer, NOSLEEP-lancer, LONLEY-lancer or just BORED-lancer.

So how do you make sure you’re a happy and successful freelancer? Here are the six things I’ve learned in the past year.  

There is nothing more valuable than a great network

The power of (and support from) my network has been by far the most positive and encouraging aspect of the past year.

I knew I had a big, very well connected network. I also knew that in a small place like Auckland (and New Zealand on a whole) – where everyone knows everyone – this network would be very valuable.

So the first thing I did when I started to look for work was get in touch with people I knew. Before I knew it I had several work offers in front of me.  

What surprised me was the kind of people and connections that popped up.

One of my first jobs came to me thanks to a connection from a friend of a friend who I had met once for coffee a few years ago.

At the time, she was thinking about a career in marketing and wanted to talk to someone in the industry (me).

Now, years later she saw on Facebook that I was looking for work and connected me to someone she knew who was looking for marketing support.  

The lesson here is; you never know who can make an introduction for you so make sure you keep track of your network and have ways to connect with them.

LinkedIn is great for that. I generally make it a point to add everyone I interact with on LinkedIn so even if I don’t speak to them for years, I still know how to find them.

Email addresses and phone numbers can change as people change jobs. LinkedIn won’t.

Pro Tip: Look after your network. And don’t be afraid to use it. Make sure you don’t spam people but the occasional message to remind people that you’re available for work can do wonders.

Know when to say NO and when to say YES

When I first started out, I basically accepted every job that was offered to me.

I think that’s natural and necessary when you start out as a freelancer because you don’t know yet what market demand is like and what types of jobs are available.

So unless you can afford to be without income for a few weeks you basically have no choice but to say yes to everything.  

But in my case, it meant I ended up doing a lot of work I didn’t enjoy.

And because I was busy doing that work I wasn’t looking for new projects anymore and missed out on jobs that would have been a lot more interesting and probably also a much better fit for my skill set.

I’ve learned that it’s important to find the right balance.

I sat down and figured out how much I need to earn to pay the bills and now make sure I have enough work to get me there – and sometimes that means accepting jobs that are not super interesting.

But the rest of the time I make sure I have work I enjoy. Sometimes that means I have a few slow weeks before the next ‘right’ job comes up. And of course it sometimes means I miss out on opportunities to earn more.

But to me, doing work I enjoy is more important that money.  

Of course, you might feel differently about this. For you, earning a lot of money might be the most important thing right now. Or it might be flexible hours, specific types of clients or something else.

Regardless, by understanding what matters most to you and knowing how much you need to earn to pay your bills you are in the best position to know when to say NO and when to say YES.  

My Tip: Work out what matters most to you and how much money you need to pay your bills. Those are the two key factors that will help you decide when to say yes and when to say no.

Find an efficient way to manage your work

Initially, I thought all I really needed was some tool or template to send invoices.

However, as my workload increased and the number of project and clients started to add up I realised I needed a better system and processes to manage my work – jobs, tasks, contacts, leads, etc.

And of course send my invoices. I also struggled a bit with the lack of visibility into how my freelancing business was tracking financially – I wanted more visibility into how much I was earning and how much I had in the pipeline.

While I really love the flexibility of being a freelancer I’m still a bit of a control freak at heart so basically flying blind didn’t really work for me.  

Luckily one of my clients, a company called Roll, actually had the perfect solution for me. Roll develops workflow management software for creative businesses and freelancers. It’s an easy way for me to manage all my work in one place. I capture leads and contacts, manage my jobs including setting tasks and tracking time and in the end, send invoices to my clients.

I also use Roll to keep track of payments (to make sure invoices are being paid on time). With Roll I have all my data in one system and can see exactly how I’m going, what I need to focus on and how much money I’m making this month – giving me the piece of mind to focus on doing great work for my clients.  

My Tip:  Invest some time into finding and setting up the right systems and processes for you. It might seem like a waste of time in the beginning but trust me, it’s worth it. Check out Roll, but there are also a number of other tools and systems out there you can use to manage your work so find the one that works for you.  

Don’t sell yourself short!

Looking back now I realise I often sold myself short in the early days – and probably still do on occasion.

The best example of this is that the hourly rate I was charging in the beginning was too low.

I basically just calculated the hourly equivalent to what I would be earning in a full time job. But that didn’t take into account that I no longer had things like paid annual leave & public holidays, an office to work from, a work computer and phone, access to things like stationery, printers, internet and so on.

Not to mention the risk and uncertainty that comes with short-term project work. It wasn’t until I had a few conversations with other people in this space that I realised I wasn’t charging enough.  

So for the next project I increased my rate – and I never got any pushback from clients.

But raising rates is about more than money.

I also, on occasion, hesitated to take on work because I wasn’t sure if I was qualified or experienced (enough).

I think it’s really important to know what you don’t know and tell a client if you’re not the right person for the job. Otherwise you end up with very stressful work and disappointed clients. In my case however, I was being a bit too cautious.

After the first few projects, and great client feedback, I realised I needed to be a bit more confident and have some faith in my skills and ability to figure things out if I don’t already know them.  

My Tip: Be realistic about your skills and experience. But if you know you’re good at something, back yourself and be confident. Don’t be afraid to request an hourly rate that’s reflective of the skills you bring to the table.  

Be clear about payment terms before starting any work

Discussing money with clients is still something that makes me a bit uncomfortable.

In the beginning I would often agree to do work without any formal agreements or discussion around when and how I’m being paid.

I invoice all my clients and usually put ‘due within 14 days’ on the invoice. But that doesn’t mean all clients follow through with that.

Some clients only process invoices monthly and have certain dates that invoices need to be submitted by. At one point a client owed me several thousand dollars and didn’t pay for over 5 weeks after I sent the invoice.

And it was difficult to chase them because we didn’t really have a formal agreement in place.  

Long story short, I’ve learned that it’s a lot easier to clarify all of this upfront. Now I usually send an email with my payment terms and ask the client to confirm that everything is all good with them before I start any work.

That way I know what money is coming in and when and am in a much better position to chase payments if they are delayed.  

My Tip: Make sure you and your client understand each other’s payment terms and timeframes before you start any work. It’s as simple as telling the client your terms or asking them for theirs prior to commencing work.

Don’t forget to enjoy the perks of being a freelancer.

Like most people who get into freelancing I did so because I wanted more independence, freedom and diversity.

But when I first started out I pretty quickly found myself basically working normal office hours, Monday to Friday, mostly at client’s offices.

And some of the work I was doing wasn’t very interesting or challenging.

I kind of ended up being like an employee that instead of working for just one company, was working for several.  

That wasn’t really what I had in mind. I’ve learned that the freedom and flexibility to work when and where I want is really important to me – more so than making a lot of money.

I want to enjoy life more.

My big passion is kitesurfing and to me there’s nothing better than being able to sneak in a mid-week session when the conditions are great and the beaches are empty and that plays a major factor when I consider taking on new projects.

I prefer jobs that I can do anywhere over those that require me to be at the client’s office during certain hours – even if that means less money.

The reality is that most projects I work on are a combination, with some time spent at the client’s office and some off-site which seems to work really well for everyone involved.  

My Tip:  Being a freelancer comes with risks and uncertainty. So make sure you also leverage the benefits of it and don’t just end up working non-stop (unless that’s what you want to do – in which case; keep going!).  

Summing it up

There’s a lot more I learned this year but those are the top 6 things that stand out for me. I would love to know what your biggest learnings have been. Share you experience in the comments.

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  1. Great read. I’m taking the plunge soon so soaking up as much knowledge as I can from those who have been there/done that. Thank you for sharing!

  2. Hi Lisa, thank you for sharing this experience. Do you have a resource you can recommend for sample contracts for freelancing? Thanks.

  3. Nice post, had the same experience with you when I started my freelancing. Talking money makes me comfortable until I realized that if talking about value dnt make me feel uncomfortable, then money shouldn’t because in freelancing, it is simply an exchange of value for money. More like trade by barter system.

    I also agree with you on the idea of payment terms. I will also add that such terms should be put in writing plus consequences of late payment, some clients are funny sometimes.
    Nice post

  4. I’ve just done the very thing—I’ve quit a job and am jumping into the freelance world. Thanks for the tips, and for emphasizing the value of networking. You never know where your next opportunity will come from.

  5. I found myself in an unexpected situation in a very niche market area. Still getting established and I know it will take time but the list is very helpful and its great to see you doing so well. I am excited about the future and will make use of your experiences moving forward.

  6. Nice tips. In my experience as a newbie freelancer, I started with a very low hourly rate since I am still building my reputation on the freelancing platform.

  7. Thank you Lisa, For being so honest, and writing a great article.

    What you have mentioned is a clear reflection of my life right now and what I have encountered with clients in the past and as how professionally I deal with them at present.

    I live and work in Dubai, UAE and you work in New Zealand. Regardless of where we are geographically, it’s the same as a freelancer.

    It’s entirely up to the individual freelancer themselves as to how robust of a life you’re going to have professionally and personally.

  8. Good points Lisa. I’ve been self-employed for 25+ years and can say it’s not for the faint-hearted. Having (and maintaining) a network is crucial as is believing in yourself.

    As an aside, I visited your beautiful country years ago (I was in Auckland and New Plymouth).

    Best of luck with your business.

    1. Thanks Shawn. Glad you liked my post and can relate.
      I’ve actually just come back from a weekend of surfing near New Plymouth 🙂 It’s a beautiful spot.

  9. Hi Lisa,

    You told a really recognisable story, I had the same struggles and also doing kitesurfing at the times when I like to do. For me it’s difficult to get clients react quickly, most of the time it takes ages before a project is finished… That’s important because otherwise I earn insufficient money. Do you have any advice?

    1. Hi Bert. I totally know what you mean. I currently have a client who asked my to do work for them 4 weeks ago and we still haven’t started because they still haven’t managed to get organised internally. In general I find sometime people don’t seem to respect your time as much when you’re a freelancer. They sort of just think you will sit and wait and be always available when they are ready to move ahead.

      To be honest, I still haven’t really found the best way to deal with it. In most cases open and direct communication seems to help. I set a very clear expectation with my clients about how much time I allocate for them in which timeframe (e.g. 5 hours per week) and that I have other work during the remaining time and might not be available to them. I also always try to set a clear timeframe for a project. For example, I say to a client I have allocate 6 hours per week for the next 4 weeks to this project. I then set very clear milestones together with them around what each of us needs to do when to make sure we complete the project in the given timeframe. I always make sure that my clients understand that I work on a number of projects at any given time and might not be available for longer / additional hours unless agreed upon.

      To be honest, this approach doesn’t always work. But in most cases it does make a difference is clients understand your availability and time constraints.

      I hope this helps a bit. Super keen to hear other options on what has worked for you and others to deal with this challenge.

  10. Thanks for the tips! I find myself in a similar situation, with only about 6 months freelancing under my belt. My biggest struggle right now is learning that I don’t have a ‘regular job’ and embracing the perks of being a freelancer, just like you mentioned above. It’s comforting to know other people in my position go through more or less the same issues!

    1. I just jumped in full as a freelancer and can see how all these scenarios can play out for each one of us, I love Millo’s blogs!

      I like to remind myself the WHY I made the desicion of freelancing so that I can really enjoy the journey:

      – Because I dislike the 2 hour daily commute to an office

      – To have a healthier lifesyle

      – To spend more time with my children & wife

      – Because I was making a rich company become richer!

      – Because I like variety of projects

      – Because I can meet a lot of new people

      The list goes on! Like many things I think we shall never forgot the WHY!

      Ohh also, always remember your Boss who loved to play Creative Director!


      1. Hi Shalom. Great comments. I totally agree. When things get tough it really helps to remind yourself why you choose freelancing in the first place. Do that I often realise that the pros by far outweigh the cons.

  11. This is an amazing list! I think it is something that every freelancer should read because being an at-home worker is great but it definitely has drawbacks. Thank you for sharing 🙂

    1. Hi Robert, thanks so much for your great feedback. It’s always good to know that others feel the same way 🙂

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