My wife gave birth to our third son on June 6th. What an absolute miracle!

paternity leave freelancing
I realize this photo is a stretch for the topic being discussed! 🙂

With this being our third go around since becoming self-employed, I feel like it’s taken a couple tries to find the right approach to paternity leave. How much time should I take off? How do I find a balance between enjoying our newest addition and providing for my family?

If you’re a freelancer and have (or plan to have) kids, you’ve probably asked yourself these very questions.

Here is some food for thought.


The great thing about having a baby is that you have approximately nine months to plan for it. While some babies come early, there is little reason to surprise your customers the day that your child is born. 

The following timeline seems pretty effective for keeping clients in the loop:

Earlier is better. A few days after you tell your family that you’re expecting, go ahead and let your customers know as well. Not only do they want to know for business reasons, but they are also genuinely interested in you as a person.

Bring it up occasionally. As the pregnancy progresses, make a few casual comments about the baby. This will remind customers that the due date is approaching. It’s also a nice way to break the ice.

Set clear intentions. Within a month of the due date, directly remind your key contacts about your approaching time off. Remind them that nothing is set in stone, but you intend to be gone for an approximate number of days.

Hope for good timing (but don’t expect it!). With our most recent pregnancy, Mandy started going into labor on a Monday around noon. This gave me time to send emails to all of my customers. Of course, some babies decide to come at less conducive times. If you’ve done a good job on the previous steps, most clients will be more than understanding when you finally have time to reach out.

Don’t Work at the Hospital

I may be guilty of doing this in the past. Although, with this baby it felt really good to not do any work while at the hospital.

Having a baby is a very special time, one that is not worth any amount of money in the world. While it may be tempting to fire up your computer, check email, or even bill some time, I would argue that it’s not worth it.

You also need to think about how it looks to your clients. Are you desperate for money? Do you not care about your family? It’s probably just best that you enjoy the special time and stop worrying about work.

Consider it a Vacation (an Expensive One)

Most people think of a vacation as a trip to the beach. However when you’re self-employed and you pay for your own insurance, having a baby is kind of like a vacation. You’re away from work, it’s kind of expensive, exercise is a distant memory, and you get to eat some pretty decent food. Oh, and of course you get a lot of quality family time.

If you don’t have maternity coverage (like us), a new baby can be expensive. Without the right perspective, all the looming medical bills could sour the experience. Keep the right attitude and remember the reason you’re there.

You’re bringing a new human into the world. Enjoy it!

Ease Back Into Things

I decided that I would officially “go back” to work on Monday, June 13th (1 week after the baby was born). To prepare, I spent a couple hours checking email on the Friday before, so that I could hit the ground running.

Try to find an hour when everyone is sleeping to do this type of check-in. With all the diapers to change and overdue housework, your family has its hands full. I realize you’re already sleep deprived, but what difference will another hour or two of sleep make?

Enjoy the New Life You’ve Been Given

Above all things, paternity (or maternity) leave is a time to slow down. Trust me, I know it’s hard to slow down. You’ve built your freelancing business by staying super-busy. Just have faith that everything will be OK.

Best wishes and prayers for the children in your life.

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Matt Keener is the original "Executive in Sweatpants," having built a successful online consulting business (from home). His best-selling book offers tips for capitalizing on outsourcing and freelancing. Matt holds an MBA and has been featured by many recognizable brands, including Upwork (formerly oDesk), Elance, Insightly, the Dave Ramsey Show, and

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