How to Get the Most out of the Holidays with a Side Hustle

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

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The holidays are such a fun time.

It’s everyone’s chance to tear away from work, spend time with people you love and in general take a break.

Unless you’ve got a side hustle.

Then you’re left wondering how to get the most out of the holidays while still keeping up with your side hustle.

For side hustlers, a break from your full-time job is your chance to catch up on all the work you couldn’t bring yourself to do during the normal workweek.

Here’s the thing though, you can’t do that for forever.

And, if you’re not careful, you end up missing out on a huge chunk of valuable time that you may never be able to get back with friends and family.

My Story

I have a blended family. I have 3 daughters from a previous marriage. You can read more about that journey here.

My wife and I split half of our week with the girls, and the other half as newlyweds (we haven’t been married THAT long, okay?!)

It dawned on me a while ago that I only get 26 weekends and 1 major holiday with them a year.

When that hit home I decided to make a career switch. I realized I couldn’t afford to miss holidays or weekends worried about getting a deadline finished for a client so I could support them.

I knew something needed to change.

I needed to figure out a way to make the most of the time I had with them.

There’s Hope

But I found out that just because you’ve got a side hustle doesn’t mean you’re doomed for a life of filling your margin trying to get things done for your after-hours work.

There are some things you can do to make sure you’re not missing those moments and put your mind at ease.

So, when you ARE spending time with your family you’re not actually worried about your business.

1. Know What You & Your Family Need

Not everyone or every family is the same.

There are different seasons in life that will require more or less from you when it comes to the relationships you have.

So, the main thing to do is determine how much time you need for yourself and how much time your family needs from you over the holidays.

You do that simply by asking.

I know that seems so simple, right? But, have you done it?

Have you sat down with your wife or kids, mom or dad and talked about what their expectations are for you and your side hustle over the holidays?

I tend to believe that most people are reasonable.

If you make an effort to consider their hopes and dreams for the holiday and then communicate yours you’ll likely be able to come to an agreement where no one’s shouting at you to put your phone down at lunch.

The problem is when we spring a side hustle deadline on our family the morning of Christmas Eve.

So, take your significant other aside tonight. Have a glass of wine together and ask them what they are expecting over the holidays for you and your side hustle. Let them process it verbally (albeit candidly and unfiltered), or give them the space they need to internalize the question, consider their calendar, and come back to you at an equally romantically-intentioned space in a few days. The response will be varied, but the appreciation and conscientiousness will likely be reciprocated. Take the first step.

2. Do the Prep Work

I’m convinced that lack of time has much less to do with not having enough as it does with HOW WE USE the time we have.

I was at a conference recently where a speaker asked the audience how many people felt like they didn’t have enough time to do everything they needed to do.

Nearly everyone raised their hands.

Then he asked how many people watched at least one show on Netflix this last week.

Nearly everyone raised their hands, again.

If we’re honest with ourselves we’ve all got a fair bit of free time on our hands. We’re just not using it in the best way.

The best thing you can do to make sure you’re not scrambling to get things done before your dad starts slicing up the turkey is to MAP OUT YOUR PROJECTS BEFOREHAND.

Remember school?

You’d get this awesome thing called a syllabus at the beginning of the semester. It was a magical piece of paper that would tell you all the due dates, quizzes and tests.

Having a side hustle isn’t like that.

No one’s mapping timelines for you. You’ve got to figure all of that stuff out on your own.

Most people with a side hustle determine whether or not they have time for a project by tossing a coin up in the air.

If it lands on heads, they say yes. If not, well, they’ll probably still say yes.

The problem is THAT IS A HORRIBLE WAY to maintain a side hustle, especially over the holidays!

You have to have a better way of determining timelines than your best guess.

When you’re just getting started this is hard to do. But, over time you begin to see patterns in how much time it takes you to do certain things.

For instance, after a while, I noticed that it would take me about 10 hours to do a home page once I had everything I needed.

How did I know?

I timed myself.

I use an app called Toggl to time different tasks I’m doing.

It helps me know what tasks eat up most of my time during a project and in the long run, tells me how much I should be charging.

So, what should you do when you first get a web design project for your side hustle?

If you answered start looking for the right color palette you’d be wrong.

You map out a project in segments and then assign a time frame for each of those segments. Then you look at your calendar and see when you can fit in time for each of those segments according to what you already have going on.

This will help you know if you have time for the project in the first place OR it tells you what you need to communicate to the client about what they can expect.

Which leads me to my next point.

3. Set Good Boundaries with Clients

It’s no one else’s job in life to set the boundaries you want EXCEPT FOR YOU.

If you let other people determine your boundaries for you, be prepared to have an absolutely miserable life.

This from a recovering people pleaser.

When you’re working hard on your side hustle it’s so easy to just say yes to everything in fear that if you use that scary word that starts with an “N” and ends with an “O” you won’t get the job.

The honest truth?

“No,” is your best friend.

“No” will keep you out of a lot of trouble and has the ability to keep you healthy and sane.

“No” can be the difference between having a side hustle that you hate and one that you love especially over the holidays.

But you have to be brave enough to use it.

And believe it or not most clients are fine with it. And, the ones that aren’t probably aren’t great clients.

Every time in the interview stage I’ve told a client I couldn’t make the deadline they were hoping for they’ve thanked me for my honesty.

And, more times than not they’ve told me they could move the deadline around to fit my schedule better.

Because, here’s the thing, most people say yes and then just don’t do it on time.

People appreciate honesty and clients will respect you more for it.

You will gain WAY more than you will lose when you use the word, “no” when you should.

So, tell clients upfront what your blackout dates are. If the project is not done and it’s Thanksgiving just tell them you won’t be working on it. The truth is, they probably won’t be available to get you the content you need to complete the project anyway. They ALSO have turkeys on their tables.

Most people understand that you need a break and will work with you if you’re upfront about it.

4. Schedule Your Day

In some cases, you might not be able to get around it. You might have to work some on your side hustle over the holidays.

It doesn’t have to be the end of the world, though.

If you know you need to work a few hours on your side hustle over the holiday you could always wake up early and knock out a few things. OR stay up later when everyone is Black Friday shopping and all the kids are sleeping.

Just like a normal day, there are moments that aren’t 100% filled with other stuff.

The key is to schedule out your day and talk it over with your family.

Don’t do it on the day of Thanksgiving. Let them know a few days before that you’ve got a few deadlines weighing on you that you have to finish.

Then ask if there’s space in the day for you to work.

More than likely you’ll be able to work something out.

My wife and I have even used time in the car to get things done. She’ll drive and I’ll be busting something out on my laptop.

It’s all about intentionality and communication.

5. Be Fully Present

After you’ve scheduled out your day make sure that YOU BRING YOUR WHOLE SELF to the time you’ve set for being with friends and family. Start a conversation. Ask someone else about their recipe. Get invested in people while they are in front of you. This will help them see you are making an effort in every sphere, and not just focusing on your side hustle during a longer than usual ‘bathroom visit’. These are relational seeds that harvest when you *do*need to make an exception for a last-minute Black Friday unresponsive website emergency (please see #6 to decide if this is a real emergency).

A good to-do list can really help with this.

Without those, it’s like there are all these little flies buzzing around in our head. We know they are there but we don’t put enough effort into getting rid of them. So, they annoy us the entire time.

I have a note on my computer called “Brain Dump.” When I’m feeling overwhelmed I write down absolutely everything I can think of that needs to be done.

  • Clip my fingernails
  • Shave
  • Finish the revisions on the homepage for my freelance client
  • Finish wireframes for the redesign at Showit
  • Hang the shelves in the baby room

Those are all legitimate things by the way ?

There’s just something about getting it out of my head and onto paper that helps me not think about the tasks I need to get done so much.

Doing things like that can help you give your full attention to the people right in front of you rather than worrying about the things you need to get done for your side hustle.

Another thing I like to do is leave my phone in another room. I don’t just turn it off or silence it.

I put it behind a door in a room that I’m not in.

Whatever tricks you have to stay focused on the people right in front of you DO THEM.

The bottom line, just stay present when you agree to be there.

6. Pick Who You Please

Sometimes it’s inevitable.

Thanksgiving dinner is going along great and all of a sudden you get a phone call from a client. Something has gone wrong and they need your attention immediately.

What do you do?

After you’ve done everything you can to communicate how you don’t work on certain hours over the holidays.

After you’ve done everything you can to communicate with family and friends what your schedule is and what they can expect of you.

You’ve got to make a choice.

Who are you going to please?

You can’t please everyone and it’s crazy to try.

So, you’ve got to pick. Family or clients?

My suggestion: pick your family.

Clients don’t love you as the family does.

Clients aren’t there for you when you’re really struggling.

The worst that could happen is you lose a client and they give you a bad review.

That’s nothing in comparison to losing a mom, dad, son or daughter.

The key is you’ve got to make the decision now. If you wait to make it right at the moment it’s so natural to go to “what’s on fire” so to speak.

If all else fails you can tell them you’ll call them back or work on it as soon as the time you’ve set aside for them comes around.

Believe me, it’s not the end of the world for them OR for you.

And, your family is MUCH MUCH MUCH more worth it.

Wrapping Up

There’s this really popular idea amongst entrepreneurs these days.

It goes something like this:

“Grind, grind, hustle, hustle, NEVER STOP WORKING!”

The problem is people only SAY that. No one’s ACTUALLY DOING IT.

I consider myself to be a pretty hard worker. I put in hard work every single week typically on multiple unrelated projects.

But, I’m not always working. I can’t. No one can!

I know that I work better when I spend time pouring into my family and taking time for myself to recharge.

I’m more productive, more creative and much happier when I’ve made sure I’m doing what I can to rest recharge and spend time with the people I love. When I go to the gym and also come home for dinner.

So, don’t sacrifice your entire holiday on your side hustle.

If you work hard beforehand and make sure to communicate to both your clients and your family you can have an amazing holiday that you will remember for the rest of your life.

Wreath on a Door


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.



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