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5 Mistakes New Freelancers Make

The freelancing life can be a dream. Skipping the traffic of the commute, waking up late to work in yoga clothes, going to spin class in the middle of the day when it’s not crowded. No demanding boss, no annoying coworkers trying to take the credit. Ahh, this is the life.

Yet, for first-time freelancers, it can be a big life change to work for yourself. And, running your own freelance business does not come without some challenges.

When I started freelancing, I was excited to live life on my terms. I had gotten an adorable puppy to keep me company while I worked from home, I had lined up my first clients, and I was ready to take this “working for myself” thing head on! But, if I’m being honest, I wasn’t completely prepared for it. My puppy got separation anxiety when I actually left the house on the weekends, not all of my prospects turned into paying clients, and I stressed out about working for myself a lot more than I thought I would. After a few years, I’ve got it under control, and I want to share with you a few mistakes I wish I hadn’t made along the way. Here are a couple of things I wish someone had told me before I got started – and some tips on how to set yourself up for success when YOU start your freelance career!

1. Prevent the loneliness

There are some days in an office when you think that if one more person tries to talk to you and distract you from your work, you will scream! But when you work alone, and especially when you work from home, you will really miss people. Yes, even the annoying ones. After days on end of working from home (and only spending time with my puppy), I really craved real human interaction. The emails, phone calls and Google Hangouts I had setup with my clients weren’t exactly cutting it, and I started to get seriously lonely.

How can you prevent getting too lonely? Proactively schedule coworking dates with friends who also have flexible schedules! I scheduled working for part of the day with a friend who was also a freelancer, and scheduled an afternoon Soul Cycle class with another friend who could take time away from the computer in the afternoon. If you’re really missing the social interaction, invest in a desk at a coworking space. It’s okay to be a social creature!

2. Get organized (to get paid)

When you work in a big office with an IT department, an HR department and a Finance department, you don’t have to do much other than fill out the forms at the beginning of the year to get paid. You bring in a copy of a check to setup direct deposit, you work hard, and voila! You get paid twice a month.

This is a completely different story when you work for yourself. When you are the one in charge of your paychecks, you have to manage and track your time, send invoices, follow up on invoices (and sometimes follow up on invoices again), setup business bank accounts, calculate taxes, fill out tax forms, track expenses, and more. This means you better be ORGANIZED!

When I started out, I didn’t realize how much time – and how many steps – went into getting paid. And then, I didn’t get paid for any of my work right away. (Maybe it was because I didn’t send out the invoices yet?) A friend recommended that I use a time-tracking and invoicing system called Freshbooks, and it has been a godsend. As a freelancer, you will be that girl with all the business organizational apps on your phone, because it will make your life so much easier. Try some of these apps from a post I wrote recently to get yourself organized.

3. Follow up, follow up, follow up

Unfortunately, just putting your nose to the ground and working hard will not make you a good freelancer. You can be the most talented web designer in the world but if you can’t network, follow up, and be persistent, you won’t land any business. More importantly, building meaningful personal connections and always “being on the radar screen” is important to the success and longevity of your freelance career.

(Insider secret: Most, if not ALL, of your income will come from clients you have worked with before, or from personal referrals from people you have worked with before.) 

I am not amazing at organizing my email inbox, and have struggled valiantly to follow up regularly. When I started freelancing, this was a big issue. I’d have great conversations with people at events and think they’d be a wonderful client to work with, and then I wouldn’t send the right emails to followup to make it happen. And a month later, when I finally got back to them (oops – ugh!), the project opportunity to work with them had passed. I had to followup more if I was going to make this work.

Make follow up part of your routine. Set yourself a schedule to write to your clients once a week with an update, or potential clients, every few weeks. Stay in touch with people who are well-connected that might refer your business, and attend networking events where you know your clients might be (so you can say hi). You don’t have to write long emails, just send an article they might like. Try using Boomerang for GmailFollow Up Then, or simply adding reminders on your calendar to follow up with someone who says they aren’t ready just yet to work with you. Believe me, freelancers who follow up are freelancers who win business!

4. Manage your cash flow

Freelancing or consulting is an exciting business model because of the lack of overhead costs. You need your computer and your brain, and you’re in business! But, when you start freelancing, you need to give yourself some time to establish yourself and get new clients. And it is stressful to not have any money or any prospects for money for 30-days out or more. While I’ve never run into the problem myself (phew!), I know several freelancer friends who have panicked about making rent at the end of the month because of the timing of checks processing at the bank.

When you start off, set aside a little seed money, and keep a little bit of money around – i.e. in your savings account – at all times. The cash flow of freelancing can be very uneven. Even if you start off with a million projects, it may be a little while before you actually get money in the bank. You bill at the end of your work, they have 30 days to pay you, they’re often late, and all of sudden, it’s 3 months later and you are only just getting access to the money earned for your hard work.

And why do you need to keep saving? As a freelancer, you will not be paying taxes directly out of your paycheck each month. You need to be prepared to pay a lot in taxes come April. Don’t let it throw you off, so be prepared for it. The cash flow issues stressed me out, especially on how to do my taxes, so I decided to work with an accountant to get me on track. It has been completely worth it for me, so if this is not your strongsuit, consider hiring one!

5. Ask for help

In corporate jobs, there are onboarding trainings, all-hands meetings full of professional development activities, and training libraries ready to use whenever you need them. There are people at the office you can ask for help with anything, from understanding your health insurance to using the right template for a project to using the paper cutter.

As a freelancer, these resources and guides don’t exist and you will feel clueless. Completely clueless. I had no idea about the taxes (see above and my amazing accountant), and I was overwhelmed by organizing my schedule. And there was no “how to be a freelancer” roadmap, in the way that there was a clear job description when I was an Editor. The best way that I learned how to navigate the waters? I asked other freelancers. Listening to their tips, stories and advice has helped me tremendously. When you have questions, ask someone. I guarantee you, they’ve been through it and would be more than happy to save you the time and pain of figuring it out on your own!

Moreover, there are so many resources for freelancers online that I’ve become dependent on! I pulled together a list of blogs that will be useful to any freelancer. You can also turn signup to be a member of Freelancers Union, or check out resources from the Small Business Administration or your local Chamber of Commerce on setting up a business.

You can absolutely get the answers you need to successfully build your dream freelance career!

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3 comments

  1. just trying to help Replied

    Hopefully the accountant also set you up with the required quarterly estimated tax payments? It’s definitely not just due in April for those of us who are self employed!

  2. I think the cash flow item is what I struggle with the most – I would love to finally go fully freelance, but I can’t imagine how that’s possible for anyone without at least 6 months living expenses saved up! (probably more??) I often wonder how confident people are when they finally take the leap …

    Anyway, thanks for this post and all the great resources – I always get excited about my future freelance life. :)

  3. Amanda Replied

    it’s funny, this post just made me SO happy that i’m not freelancing any more. i tried it for 2 years and about 2 months ago landed a dream job at a tech startup. now i can focus on my career without having to worry about all those little things mentioned above, and i’m making way more money. i totally applaud those who freelance and make it work. good on you! i just found it wasn’t for me.

    another little resource i use for networking is meetup.com. great communities doing cool stuff. through one of the meetup groups i’m in i went to a UX talk on Big Data at Google last night!

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