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How I freelance through the holiday season

Tis the season to spend money.

Booking vacations to relax or travel time to see family.

Buying more than usual due to all the tempting sales from Black Friday and Cyber Monday.

Starting your gift gathering.

Money just burns through our pockets this time of year.

I know it may sound crazy sound crazy but, the holiday season is the best time to make money.

While most people are thinking about Black Friday, Cyber Monday, and overall holiday shopping. I like to shift my focus to earning more this time of year opposed to spending more.

I’m a regular guy, and my pockets are burning just as much as yours but… I’m looking to offset all the spending. This happens by switching my freelance model up a bit.

3 things are likely to happen this time of year which makes a perfect storm for some holiday freelancing

  • My day job slows down to a crawl
  • Clients are busy with their personal life
  • I’m in the house much more

Without further adieu, let’s get into the details!

Day job is slowing down to a crawl

Meetings are fewer. People are on vacation. Deadlines are pushed back.

Needless to say, it becomes a real challenge to get the same amount of work done during this time of year compared to the rest of the year. This results of very “shallow work” or just less work.

I’m usually operating at a fraction of my typical workload resulting in me having more energy to do things outside of work.

It’s also common for my boss to tell me just take the day off due to the normal operations slowing down so much. Believe it or not, I very much welcome surprise days off.

In the past, I would just take the day, go home, sit around and look lost because I’m used to working during that time. When I ask my co-workers what they plan to do, it’s often the same, go home and harass their pet until their kids come home to resume the usual schedule.

This is a prime time to freelance! I’m already in the mindset of getting work done and have time during the day to do so.

If you’re salary, you are doubling up your income for a day. If you’re hourly, you’re offsetting a slow day at work. Sounds like a win-win situation to me.

If you have the luxury to freelance from home (which you should be doing!), it’s that much more of a win since it feels less like work when working from home. Especially when you’re used to going into an office daily.

Clients are busy

This is an unexpected plus for me that use to make it horrible for me this time of year. Especially when I freelanced full-time.

In the past, I would starve for work because my client would be on vacation or just too unresponsive to get anything worthwhile done.

Literally, the same situation people have at work that results in slow days.

The difference here is that you have more control over things.

Opposed to letting things get slow, around the start of fall I tell the client I have a retainer of 10 hours minimal to manage my bandwidth more through the holiday season. Surprisingly, I have yet to have a client be against it. From their perspective, they are having me do well over 10 hours of work a week.

This also incentives them to do one or 2 things

  • keep steady work flowing in by giving me more ownership of the work I should do or beefier tasks to keep me busy
  • keep me retained and prevent me from leaving their project resulting in them needing to replace me

Either way, it’s a win for both of us.

A side effect of getting more ownership over the project and tasks I work on, it positions me to introduce the possibility of a rate increase.

When freelancing, more ownership results in more pay. Just pitch the benefits to the client using this time frame as an experiment to justify your pitch.

For whatever it’s worth, each time I was giving more ownership to make decisions opposed to a beefier task, it always resulted in an increase in rate.

Pro-tip: Getting to know your client is essential. During this time of year, things can get more casual as everyone is winding down and taking a break. I often find myself having more casual conversations with my clients about common interests, family, etc. This helps as it strengthens the working relationship. Take this opportunity to get to know your client, it works in both you and their favor.

Pro-tip for the other pro-tip: Double down on client relationship and send an Amazon gift card based on something you spoke about during this casual time. (Sorry for the pro-tip inception!)

Stuck in the house

I live in Michigan. Around this time of year, it’s dark at outside at 4:45pm and usually cold enough to deter you from going out as much.

This is the perfect recipe not to leave the house!

Not to mention most of my friends/family are in the same boat, resulting in me being home all the time. While I’m saving some money on not going out as much, I’m still at home bored out of my mind.

I think it goes without saying, capitalize on this situation if you live in a similar climate.


  • capitalize the slow days and unexpected off days
  • make sure you have worked lined up from your client
  • take advantage of the increased home time
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© freelance after five 2019
no gmo's, gluten or themes were used in the making of this!
by @FreelanceAfter5