Freelancers’ Fall Checklist

Freelancing Basics | Sep 08, 2016

As the first leaves start turning yellow, many of us who are well past our school days can’t help getting into a ‘back to school’ mindset. For a kid, this time of year might mean buying some new clothes or a fresh knapsack; sometimes it involves digging out books or notes from the previous year, picking courses, or figuring out a route to a new school. Often these activities are accompanied by a combination of dread and excitement. Dread because the more carefree days of summer are quickly fading into the past, and excitement because a new school year is a chance to learn new things, make new friends, and get a fresh start.

Fall is also great time for freelancers to step back and take a clear-eyed look at how you’re doing. It lets you head into the next season tuned up and ready to go. Traditionally September to early December is a busy time of year, so when better than these last hazy weeks of August to take stock of your life as a freelancer and make some changes to help you make the most of the new season?

This checklist may look daunting. Our goal is to surface the range of areas you should consider re-evaluating. Not all of these will need your attention, so it’s up to you to focus on the ones that will have the most impact.

 The Checklist:

    1. Review Your Finances. Have you collected all money owing to you? Are you saving enough? Have you put enough away for taxes? Are you capturing all your expenses to minimize your tax bill? If not, set aside some time and get this done. You’ll thank yourself next March when you’re completing your taxes.


    1. Tools Update. Are you taking advantage of some of the new apps out there? Are you effectively using your tools or have you developed inefficient workarounds? Have you downloaded the latest versions? If you’re on the go a lot, do you use mobile apps that will move things more quickly and/or help your organize your workload? Are there email lists you should unsubscribe from? (Unless they’re very good, at best newsletters can be a productivity suck and at worst they can add noise and clutter to your inbox).


    1. Review Your Client List. Who have you worked for in the last 18 months? What are they paying you? Who are your repeaters? Who haven’t you been in touch with that might be worth connecting with? Who are you charging rates from 3 years ago that you need to flag for an update?


    1. Review Your Work. Take a look at your last 6-12 months of work. A hard look. Are you still doing work you can be proud of? Is any of it getting stale? Repetitive? Uninspired? Get a trusted colleague to give you feedback. Be your own critic and try to figure out what you need to do to get back to producing the kind of work you want to be known for.


    1. Professional Development. Are there skills you’ve been meaning to learn? Courses you’ve wanted to enroll in but haven’t found the time? Books you’ve wanted to read? If you find conferences beneficial, have you checked out what’s coming up so you can plan to attend? Professional development takes time, whether self-taught or through a third party. Identify what you what to learn so you can plan for the time and money it takes to actually do it.


    1. Consider Your Marketing. Are you happy with your use of social tools? Does your portfolio/website/Facebook page need a refresh? Have you checked the analytics tools to review where your traffic is coming from? Does your brand need an update? When was the last time you met some new people? What else can you do to draw more attention or land new clients?


    1. Social Supports. Are you happy with where you work? Are there alternatives you’ve been meaning to explore, such a co-working spaces, a local library or others – but haven’t had the time? Do you have enough social interaction during the workweek or is it time to join a meetup for freelancers? Are there people you’ve been meaning to get to know, either because you like their work or you think they can offer advice or insight about freelancing? Find a friend in common who can introduce you to them or send them a message. If you don’t have their email, try to contact them through LinkedIn. Most people are generous if you don’t waste their time.


A tune up is defined as “a general adjustment to insure operation at peak efficiency” or “a process in which small changes are made to something (such as an engine) in order to make it work better.”

Even those of us who are happy and successful freelancers can benefit from a little tune up every now and again. Although it takes self-discipline and valuable time, it can help you gain better control of your life as a freelancer and fulfill the freelance promise – to make a decent living, do great work and get professional and personal satisfaction from your work.



“Freelancers’ Fall Checklist” was originally published on in September, 2015.