How to Navigate Tough Times in Your Freelance Business and Come Out On Top

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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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You’re going to face tough times in your freelance business. How you handle them can make the difference between you coming out on top or having to shut down entirely. Check out this podcast to hear my own personal journey through a tough season and how you can thrive no matter what you’re facing.

I got Covid-19 this last week. Not just me but my whole family.

Me, my wife, Sarah, my kids all the way down to my two-year-old.

Covid sucks, like a lot. BUT, having Covid when you have to take care of your kids who also have Covid is way worse.

Thank God for my wife Sarah!

Unfortunately, it gets worse.

This was just the cherry on top to a really tough season.

4 days before I got Covid I had just returned home from spreading my dad’s ashes. He passed away 3 days before Thanksgiving in 2020.

Can I be real for a second?

I haven’t felt like doing much at all. The proverbial “wind in my sails” has almost completely be snuffed out.

If you get my newsletters you’ve probably noticed that I haven’t sent many out lately if any at all.

And listen, I hestiate to mention my dads passing as it might cheapen the whole thing. And, I want to honor him as best I can.

But, I can’t help but think that there are probably some other folks out there that are struggling right now, too.

You’re facing some tough situations and you can’t seem to muster the energy to put into your freelance business or side hustle like you once did.

What Do You Do During Tough Times in Your Freelance Business?

So, I’ve been battling the question, “How do I keep going when I want to quit?” or “What do I do during tough times like this in my freelance business?”

This is certainly not the only time I’ve faced this question BUT it’s definitely made me consider it again.

So, here are some things that I have found that help me keep going. Hopefully, they’ll serve as some encouragement to you with whatever you’re facing so you to can keep moving forward even if you feel like giving up.

Here are 9 things that can help you keep going when your facing tough times in your freelance business.

1. Figure Out if Your Problems are Self-Inflected

At the very start, we should probably clarify that there are two very different sources of the “tough times” you might face in your freelance business. Those are:

  1. External Issues
  2. Internal Issues

External issues are things that happen outside of your control. There the things that insurance companies call an “act of God.”

So, things like a global pandemic OR a flood hitting your city and washing away your laptop. Pretty rough…not much you can do about those things.

Internal issues are things that you do have a certain amount of control over. The degree of control you have might vary from one to the other BUT for the most part these are things that you can do something about.

Now, here’s the key:

If you find yourself always in the same situation OR there is a pattern the problem is likely an internal issue OR it’s self-inflicted.

Don’t start throwing knives at me just yet!

As tough as it is to hear, we create a lot of problems for ourselves and blame things like fate or other people.

Of course, I’m not talking about things like a death in the family. But, I am talking about things like:

  • Taking on projects with bad clients
  • Not organizing your time well
  • Procrastinating until the absolute last minute

It’s my belief that a lot of trouble you face in your freelance business can be avoided by having a little bit of foresight and learning from your mistakes of which I have made more than the average.

The issue isn’t really making mistakes as much as it is learning how to keep from making them again and again.

So, if you find yourself and your freelance business in a perpetual state of emergency it might be time to go inward and take a look at whether or not you’re creating some of the issues yourself.

The good news is, if you created the issues, then you can fix them.

2. Get an Account-A-Bili-Buddy

Nothing will help you navigate tough times in your freelance business like a friend that encourages you to keep going and gives you insight.

I am a huge fan of finding a good community to be a part of as a freelancer.

If it weren’t for my wife Sarah and the people that are closest to me, I would absolutely not be where I am today and I would have given up on a lot of things a long time ago.

A community will keep you from making rash decisions. They’ll keep you from giving up before you really should. And, ultimately, it’s way more fun to do life as a freelancer with a few like-minded people around you.

AND, best news, it works both ways. You get to encourage someone else in their tough times, too!

But, here’s the thing, a good community doesn’t happen by accident and it sometimes takes a while to find the right one for you.

You’ve got to be intentional about finding one. So, look for a Meetup group in your area. Reach out to a few people you know.

I’ve meet some great people through something called Creative Mornings. There are a lot of local chapters. AND, if there isn’t one in your area, START YOUR OWN!

And, hey, if it’s not love at first get together keep looking. There are a lot of folks out there who need encouragement just like you do and are looking for someone to hold them accountable and help encourage them to keep going.

3. Throttle Up or Down on Your Strategy and Expectations

When things get really crazy in your life you have the ability to change speeds. You can choose to switch gears with what you’re doing and how much you’re doing it.

There are 3 main gears you have in your freelance business:

  1. Growth
  2. Maintenance
  3. Pause

When you hit tough times in your freelance business it’s okay if you choose not to grow. You can either go into maintenance mode OR pause altogether.

Both of those gears are completely valid options.

So, you should probably think about and prepare for what you need to be doing to grow, what you need to do as a bare minimum and a have a game plan to pause if that has to happen.

I know personally that I struggle when I feel like I’m not in a growth season. So, I have to keep reminding myself that slow growth is still growth nonetheless.

It may be taking longer than what I planned or hoped for BUT I’m still in the fight. I’m still going.

And, you can too!

Most of us think too short term. So, if our freelance business doesn’t skyrocket in 3 years we feel like giving up. BUT, you’ve got a lot of life ahead of you.

I know for myself, I’m still going to keep going no matter how old I am, 60’s 70’s whatever! As long as I have the physical ability to keep going and a laptop I’m going to be working toward building something.

You might find other people who are awesome at just crushing their goals in life in a short season of time BUT you will be hard pressed to find someone who is willing to keep going no matter how hard it gets like I am.

AND listen, I’m not saying this to impress you, I’m saying this because I fully believe you have that ability too!

Your opportunity to build an amazing freelance business whether it’s in web design, web development or whatever ONLY ENDS the day you decide to quit going for it.

You might have seasons that you need to slow down or even detour altogether BUT listen to me THAT IS NOT FAILURE.

If you just keep going you will one day look up and find yourself have gone further and accomplished more than you through you could.

4. Create a Parachute as You Go

There’s a lot of wisdom in having the foresight to realize that when times are good you should probably be preparing for when things aren’t so good.

Now, I’m not trying to be an eternal pessismist. This is just the natural rhythm of life.

There’s a harvest in the Spring. Then there’s a Winter. If you didn’t store up for yourself in Spring to prepare for Winter, then tough luck.

You can do that by setting aside money from each project to give yourself cushin AND by finding other people to help you if you need to offload somework.

It’s never a good idea to take the total amount of money you get from a project and put it straight into your personal checking.

Now, if you’re living from one project to the next that’s another topic altogether.

But, in general, you need to be constantly setting aside a portion of your earnings for a rainy day fund. So, that when it rains, or something crazy hapens in your life, you can have the ability to throttle down a bit and focus on yourself and your family.

There’s a lot I could say about how to budget what you’re making on your projects. AND, we’ll go into that a bit more in-depth this year.

You should also try and find other people that can help you during seasons like this. That could be people that you can just hand projects off to like a peer OR it could be someone that you can pay as a contractor or an employee.

If you ever want to have a vacation OR ever need to step away for an emergency you can’t just leave your clients holding the bag. SO, find some people that can lighten your load along the way.

5. Think About What Really Matters

I’ve gotten the chance to really come back to what really matters to and my family during this season.

I’ve asked myself some hard questions like “Do I really want to be doing this? Does this really matter all that much in the grand scheme of things?”

You shouldn’t shy away from questions like that when you face tough times in your freelance business.

These can be good opportunities to reevaluate the direction your headed and whether or not it’s time to course correct.

The worst thing to do is just keep going at all costs. That’s a sure fire why to find yourself running a freelance business or doing a job you hate.

It might be that you find you’re doing exactly what you need to be doing OR it might be that you determine you need to make a few adjustments.

Either way, don’t miss the opportunity to evaluate where you’re at when you hit those rough patches.

6. When All Else Fails, Just Keep Going When You Hit Tough Times in Your Freelance Business

There’s no way to sugar coat it.

You will have seasons that you have no clue what you should be doing and whether or not it’s worth it to continue.

I’ve been there. And, it’s not fun.

I don’t really now what to tell you about what you should should or shouldn’t do. But, I can say, it’s never a good idea to make a big decision when you’re in that frame of mind.

I know personally, there came a time over these past few months that I realized my feelings weren’t going to change. My motivation wasn’t going to suddenly turn on.

If I was going to keep what I had worked so hard to build over these last several years, I was going to have to put one foot in front of the other and just keep going.

If you find yourself in that same position, I want to encourage you.

Keep going. Don’t give up. There might be a time to call it quits BUT don’t let that be right now.

I had a pastor tell me that you never know when it’s time to quit until the day after.

Now, that might sound like a Jedi Mind Trick BUT it’s solid wisdom. Most of us give up too early. We throw in the towel way before we should.

So, when all else fails, just keep moving.

Do one simple thing that you know you need to do and nothing more.

You don’t need to conquer the world. You don’t need to have the biggest month you’ve ever had. You just need to put one foot in front of the other.

Courage to Keep Going Through Tough Times in Your Freelance Business

I hope my own journey has given you courage to keep going when you face tough times in your own freelance business.

The truth is those tough times are bound to happen. So, whether or not you’re experiencing them right now OR yet to experience them at all get ready because they’re coming.

But, thankfully, it’s not the end of the world when you face them.

You can prepare for them AND if anything else I’m here to help as much as I can. Feel free to sign up for a time to chat with me.

a man at a desk with a silhouette light to represent the tough times in freelance business


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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