Paolo, we are a single-income family, and my husband is considering becoming a freelancer. What should I tell him?

You’re in a situation that’s both exciting and, let’s be real, a bit nerve-wracking. Your husband wants to step into the world of freelancing, and as a solo-income family, that decision carries a lot of weight. The first thing you should say to him is that you hear him, you see the ambition, the desire to create something on his own terms, and that’s something to be acknowledged and respected. But it’s also important to have a conversation that’s honest and grounded, because freelancing can be a fantastic journey, but it’s not an easy one—especially when you’re carrying the financial weight for the family.

Start by acknowledging that you understand why he wants to make the change. Maybe it’s about seeking freedom, being more in control of his time, or pursuing a passion that he can’t express in a traditional job. Whatever the reason, make it clear that you’re not against the idea, but you do need to talk about how this shift will impact the whole family. It’s not just his decision—it’s something that affects both of you, and that requires open dialogue and mutual understanding.

Make sure to address the financial reality head-on. Freelancing can be unpredictable, especially in the beginning. There are no guaranteed paychecks, no benefits, and often a slow start before things stabilize—if they stabilize. It’s not about discouraging him, but about facing the reality of what that leap into freelancing actually means. You want to be supportive, but you also want to make sure there’s a plan in place, so that the family’s financial stability isn’t jeopardized. This might mean sitting down and going over your current budget, assessing how long you can manage with a fluctuating income, and deciding on a safety net—how much money needs to be saved before he makes the jump.

Another thing to discuss is what kind of transition plan he’s considering. If he’s currently employed, is there a way to start freelancing on the side, part-time, while still keeping his job for stability? Can he build up a client base, test the waters, and get a sense of what freelancing will really look like before diving in full-time? This kind of gradual transition can make all the difference, giving you both a sense of security while he pursues his ambition.

Talk about the logistics of freelancing too—where will he work? How will the family’s routines change? Freelancing requires discipline and a space where he can focus. Make sure you’re both on the same page about how this new lifestyle will integrate with family life. Freelancing from home, for example, can blur the lines between work and personal time, so setting boundaries is crucial. Discuss what those boundaries will look like and how you’ll both ensure that family time remains a priority.

Also, be clear about what kind of support he needs from you—and what support you need from him. This isn’t just about finances; it’s about emotional support, understanding that there will be ups and downs, times when work is thin, and moments of doubt. Talk about how you’ll navigate those challenges together, because freelancing can be a roller-coaster, and he’ll need someone in his corner when things don’t go as planned. But you’ll also need reassurance that he’s not diving in without a plan, that he’s taking the steps necessary to make this work realistically.

Encourage him to be proactive—to start building a network, researching his market, and developing skills that make him stand out as a freelancer. Freelancing isn’t just about finding gigs; it’s about creating a personal brand, understanding the competition, and building a client base that trusts him. Make sure he’s clear on what sets him apart, what he can offer, and why clients would choose him over someone else.

Finally, let him know that while freelancing can lead to incredible freedom and fulfillment, it’s not a guaranteed path to success. It requires a combination of discipline, resilience, and a willingness to adapt. He needs to be ready for uncertainty, to face possible failures, and to learn from them. And as a solo-income family, that means he has to be extra prepared—financially, mentally, and emotionally.

In the end, what you should say to him is that you’re not shutting down his dream—you’re asking for a strategy. If he’s willing to take a thoughtful, calculated approach to freelancing, if he’s willing to be transparent with you about his progress and flexible enough to adapt if things don’t go as planned, then you’re willing to stand by him as he takes that step. It’s about finding a balance between supporting his ambitions and protecting the family’s well-being.

So, you tell him you’re with him, but that you need a plan, a timeline, and a safety net. If he’s serious about freelancing, he’ll appreciate that you’re taking this seriously too, and that you want to make sure both his dreams and your family’s stability can coexist.