Top Challenges Freelancing From Home as a Dad

Being a Dadpreneur doesn’t come without challenges. I’ve been a freelancing stay-at-home Dad since about 3 months before my first son was born. He’s now 5, and I feel like I’m just starting to figure it out. But I hope it doesn’t have to take you as long as it took me. I want to walk you through some of the top challenges I’ve experienced, and what I did to overcome those challenges. Now my oldest son is only 5, so I haven’t experienced what it’s like with older kids, but I imagine it gets easier the older they get because they start to understand more how Dad working affects their life positively. So young dads with babies, toddlers, and young children will likely face the most challenges, and that’s who I’m speaking to.

Your children want to play with you, and they don’t understand why you’re glued to your computer for several hours each day.

Since my oldest son is now 5, it’s easier to explain to him what I’m doing and how it impacts his world. But at first, there was a lot of miscommunication. He thought I was ignoring him and that I didn’t want to play. He thought I was trying to escape him, and that I cared more about my computer than I did him. Now, he understands that if I don’t work, we don’t have money, and if we don’t have money, we don’t have a place to live, nor can we buy food. Most importantly, he realizes that he doesn’t get any toys. He seems to care more about the toy part since he was born into a world expecting a roof over his head and food in his belly by default. Not all children have that.

For the first year of his life, it wasn’t too difficult because he was perfectly fine to just hang out with Mom most of the day. He also couldn’t walk yet, so he didn’t really try to bother me much. There was the occasional hand slid underneath the door and light tapping as he wondered what I was doing, but that’s more adorable than it is annoying. And even then, I would sit him on my lap sometimes while I worked or he would crawl around the office, but overall, he wasn’t bothered by me spending time on my computer working. He was in his own baby world.

But then he became a toddler and as many toddlers do, they start to break away from their mom a bit as they wean from nursing and cling onto their dad more. In his broken language, he never failed to express his discontent with my staring at my computer screen and his desire for me to play with him. So it was a struggle between the ages of 2 until about now with him being 5. When he started speaking, it did get a bit easier, so around 2 and a half there was some burden lifted in me being able to explain to him why I couldn’t play when he wanted to. He heard my words. He still struggled to understand the context but at least he felt heard.

Now he understands the world much more, surprisingly well for being only 5, but there are still limitations. And the fun part is, my second son is around 18 months, so the challenge is beginning all over again. But it is different because he has a brother to give him attention to, not just me. So I have to say, the second child is easier and if you’re starting freelancing and you already have a few kids to entertain each other, then it could be easier, but it still won’t be easy all the time.

So my best advice for Dads who are trying to work from home as a freelancer is to pause what you’re doing, look your kid in the eye and hear them out. Then tell them without any frustration, “You want to play with me. I want to play with you, but right now I have to work. I will be done in 1 hour and then I’ll take a break and we can play. What would you like to do when I’m on my break?”

You’re focusing on helping them set their sights onto the future when you will play with them so they aren’t so focused on the fact that you can’t play with them now. You’re also hearing them so they feel validated, and you’re expressing that you want to play with them. All a child wants is to be loved by their parents and to feel as if they want to be with them.

My first strategy, which was a total fail was, “Oliver, I’m working, let me work. I can’t play, just go find something to do.” And this was all with an angry tone of course. I basically confirmed his fears to be true that Dad didn’t want to play with him and didn’t want to be with him. In reality, I would rather play with him than work, but I made it seem as if I would rather work.

The reason why I emphasize being a freelancing Dad even though many Dads since 2020 are working at home, is because when you’re freelancing, you have much more control over your schedule and interruptions are more acceptable. I don’t know what it’s like to be working 40 hours per week for an employer on a strict schedule, from home. I imagine the stress and pressure is even greater when you’re working all day 5 days per week. For me, I work 25 hours per week max so my kids are used to me not starting work until 9 and being done by 4pm with at least a 1 hour lunch break in the middle. And they expect 3 day weekends every weekend since I usually take Fridays off.

So there is more balance with my schedule than there is for a Dad who is working 40+ hours per week from home. And if you’re that guy, then I encourage you to keep following this blog and watch my videos so you can learn how to work towards only having 20-25 hour work weeks. 40 hours per week is too much while you’re raising a family, it really is. The demands of family life are substantial and important.

Another challenge freelancing Dads face is the mental pressure of providing for a family and not having a guaranteed paycheck on a consistent basis.

I know what it’s like to be the only income earner and to feel the pressure from your wife mostly, as the kids aren’t aware of financial needs when they’re young. Your family expects you to provide money so you can survive. And when you’re just starting a freelance business, your income fluctuates more wildly. That fluctuation directly correlates to your skills and nothing else. These skills don’t just include the skill you’re selling as a service, such as video editing. It also includes your sales skills and communication skills. It includes your money skills and your money mindset. It includes your attitude and confidence.

But when I’ve had low times and my wife gets stressed, it’s very uncomfortable as a dad to feel like you’re a failure, to feel like your family is relying on you for their survival and you’re not providing for their needs. During my rough years, I felt very ashamed when we had to use Christmas or birthday money to buy clothes. And in all that, I’ve been blessed to have a wife that never gave up on me. She never threatened to leave me. She never stopped loving me. She knew I was trying my hardest, but that it took time to develop the skills I needed to succeed. But that doesn’t mean she wasn’t stressed. Raising a family has enough stresses on its own, so throwing in financial issues really can bottom you out.

My advice when providing for your family as a freelancer, is two-fold: gain the skills you need to find clients fast. That means studying how to sell and practicing every day. And we’ll go deeper into sales in other articles and videos. But I procrastinated learning sales for a whole year and half and I would have started making money so much sooner if I made that a priority. Two, get on the same page with your wife regarding your financial priorities, your financial plan, and how you want to spend and manage your money. You have to be completely united on that. I took on too much of the financial management and planning burden because I didn’t want to stress out my wife, but obviously it became a self-fulfilling prophecy. My not talking about it enough with her is what caused anxiety and ultimately led to us getting into $20,000 of credit debt. When I learned how to sell, I paid off that debt in 6 months.

One last challenge I wanted to discuss today is not being able to block focus.

I don’t know about you, but I naturally like hyperfocusing for a couple hours at a time and then taking longer breaks. I don’t like dipping in and out of a task. So as you can imagine, working at home with kids put me in a situation where I couldn’t go a couple hours uninterrupted. You may be thinking, “Well can’t your wife keep the kids away from you?” Ha. She’s tried. On days when the kids are occupied with play dates or other activities, it’s much easier, but some days Mom has things to get done too and the kids get bored. That’s when she can only do so much to keep them away. I don’t believe in coercing your child through threats and fear to get them to stay away and let me work, so we have to have more patience and be better planned. When we plan enough activities for the kids, then I have fewer interruptions.

And any stay-at-home parent will agree that sometimes your children just need a switch in the person watching them, and we as parents sometimes need a break from watching the kids before we get impatient. That’s another reason I only work 25 hours per week so that my wife can have breaks from taking care of two kids, and sometimes one kid is hanging out in my office playing on their own and the other is with her. That’s especially needed now when the two siblings start to get sick of each other and need to be separated.

Anyways, I’ve had to learn to focus in smaller chunks of time. That’s a reality, at least while your kids are younger. But as long as you stick with a very consistent work schedule, your kids will have an easier time not interrupting you as often, and your wife will have an easier time planning her needs and chores around when you’re working.

And in case you don’t already know, my kids are homeschooled, as you may have already guessed, so that means they aren’t away being taken care of by someone else for 6 hours per day. I can’t give advice to that working parent at home because they have several hours per day without kids. So when you do have more interruptions than you would have in an office, you need to be very diligent with your to-do lists, staying organized with what tasks need to be done for what client and what tasks need to be done for your business directly, and make sure those tasks are prioritized and include deadlines where necessary. Then when you get interrupted, you know what you’re currently working on because an app is telling you.

All in all, being a freelancing dad and “digital homebody” has challenges. I still have challenges I have to deal with, but I’ve overcome many of my early ones, and the pros far outweigh the cons. Life itself doesn’t come packaged without stress, but it’s how you handle the stress that matters. Do you respond to a new problem with frustration and blame, or calm and responsibility? Stress is a good thing when we are positively meeting resistance with an attitude of “I can solve problems. I will solve this one.”

To any freelancing dad out there, you’re on the right track. Good job on keeping your priorities straight and remembering what matters most.