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Pregnant Freelancing and Maternity Leave, FFW-Style

January 13, 2017 By FiveFigureSarah

Can you freelance pregnant? Can you take a maternity leave? Does all life end when you see that miraculous plus sign on a pregnancy test?

The answers are: yep, I don’t know yet, and nope. So let’s get into it:

I’m pregnant and due this spring! This has been a crazy, patient journey, and I was pretty terrified during my first trimester because of the health issues I’ve written about in the past. But everything’s going great and it looks like I’ll be a very lucky mom in a few months.

On my personal blog, I tackled “a day in the life” of my freelance pregnancy so far. But for you guys, I want to dig deeper into what pregnancy does to the freelancing experience.

This isn’t about how grateful I am to have the flexibility to work when I feel good or not work when I don’t feel good (though that is awesome, and I cover my approach in The Sweet Spot guide). This is about the hope I have for my career now that a) I don’t feel as reliable and b) there’s about to be a little person in my life who’s even less reliable.

So, let’s talk about it! Here’s what I’ve learned so far:

Pregnancy Makes You A Better Freelancer

I read a long time ago that parenting makes you a better freelancer. Now that’s hopeful!

I desperately wish I could find that original post, because the man who wrote it was very matter-of-fact about how much better he was at his job since he had kids.

And not just because of “the deadline paradox,” where the less time you leave for a deadline the faster you can finish it (because even if you can get away with it a few times, that leads to shoddy work). He meant that he was a different person, his child made him a better person, and the work he did was more creative, nuanced, and – yes – faster because of the pressures in his life.

He was a different person, his child made him a better person, and the work he did was more creative, nuanced, and – yes – faster because of the pressures in his life.

How awesome is that?

This is also a perspective shift courtesy of Pam England’s Birthing From Within. In her introduction, she explained pregnancy as an incredibly restorative, powerful, and creative time for a woman.

I’ve never heard that before, and it gave me the hope that maybe life would be better with a pregnant body and then a baby. Not our society’s warped view of discomfort, inconvenience, and general crappiness. But actually better.

I’ve found that to be true for me so far. Some days, I only get an hour or two of work in. And yet, somehow, I’ve met all my deadlines, added new clients, and billed well over the past 6 months of pregnant freelancing. I’ve also done the work I’m most proud of of my career during this time.

There were periods of significantly less work, and then periods of a lot of work. It all got done, and I grew a little baby human in the meantime. The two were not mutually exclusive for me — though I understand that that may not be the case next time ;-).

Pregnancy Makes You A Better Believer (Which Also Makes You A Better Freelancer)

I also have first-hand experience about how this pregnancy thing (and potentially parenting — we’ll see) forces you (ahem) gives you the ability to trust in God.

Because seriously. Much like pregnancy, this freelancing roller coaster is not under our control. We have a lot of agency — we can develop good freelancing habits like marketing and updating our portfolios, honing our craft by reading good books and participating in writing communities, and getting up every day and write.

But our careers are in God’s hands. If we’re not meant to freelance, this ship isn’t getting out of the dock.

Much like pregnancy, this freelancing roller coaster is not under our control. If we’re not meant to freelance, this ship isn’t getting out of the dock.

Fortunately, the opposite is true, too. When you give it all to God, things work out even when you don’t see how they possibly ever could. That client you gave up on calls back. Someone contacts you out of the blue to start a new project. And that’s the story of the past 6 months for me.

Clearly, it’s a give and take between doing the work and letting God bless the work, but before pregnancy I did a lot more “frantically doing the work”. The past few months, I’ve been given the grace to sit back a little and let God bless it, too.

Same goes for my brain function as a pregnant freelancer. I was really worried about “pregnancy brain” ransacking my ability to write and being a vegetable for 9 months (and then who knows how long after). But since I had to give it all to God, I did. I love this line from Peter Kreeft’s Prayer for Beginners:

“[When we ask for the grace to trust him with our thoughts…] He is the Master also of our miserable memories. A thought comes into our mind when he says, ‘Come!’ and leaves when he says, ‘Go!’ He is the centurion, our thoughts are his soldiers. The Lord giveth, the Lord taketh away, blessed be the name of the Lord.”

This has definitely been the case with me. I place every single workday in God’s hands. I still get stressed and I still wonder if I’ll deliver my best work by the deadline and all that, but in general, I have so much more peace about the work I do, finding new clients, and when I will get paid, that it’s light years better than non-pregnant freelancing.

This sense of peace and calm filters into my client calls and emails, and I don’t think it’s a coincidence that my client relationships are better than ever.

Making and Disseminating Maternity Plans

I got into this freelance thing as a way to have more say over my day. Having a high level of control over when I wake up and where I work is a huge motivator for me, and by far the #1 benefit of working for myself.

So, when it comes to a maternity leave, even though I’m tempted to just wing it and try to work, I want to plan to take some time and truly detach from work and attach to this little baby. (And then there’s that whole sleep thing, which isn’t conducive to getting paid to write.)

Having a high level of control over when I wake up and where I work is a huge motivator for me.

Here’s how I worked it out, though we’ll see if it works out: I kept the news private until I was 6 months pregnant. Then I let all my clients know the news, that I’d love to put work together in advance, and that I’ll be limiting new assignments starting two weeks before my due date to two and a half months after. (I gave a three-month date range).

So far, so awesome.

With some clients, this triggered the response that it’d be best to reconnect after the baby’s born. With others (thank the Lord) we’re going to get the work for those months completed before I take off. In the green light scenarios, l offered to set up auto-invoicing with FreshBooks so the client can still pay at regular intervals instead of having one huge bill early on. (This might not be the advice you get from everyone, but in the two situations I offered, it felt really right.)

The Final Trimester

So, here I am, power writing and power napping. I’m wrapping up projects from last year and starting projects that will be wrapped up within the next two months.

When I list out all the things to do, it seems overwhelming, but so far I’m still trucking day by day and delivering some seriously awesome work (if I do say so myself). But the best part of it all is the level of peacefulness that comes with knowing I’ll work as hard as I can — and the I’ll stop.

And then, God willing, I’ll pick it back up again and have even more to share with you guys. 🙂

You’re Invited: Freelancing Pregnancy Stories? How’d It Go For You?

Stop Trying to Overcome Freelance Writing Fear

June 7, 2016 By FiveFigureSarah

Eileen wrote me this email yesterday, and it was really heartfelt.

“It’s helpful to know that the fear is part of the freelance writing job,” she says. “Like, I guess, I tend to think that if I’m scared I must be doing something wrong.”

Boom.

Zap.

Zing.

Tell me you’ve never felt that way before.

That first day of high school, when you’re shaking with adrenaline that’s half excitement and half, “Where the crap is my locker?”

That first day on the job when you double-check your offer letter to make sure you didn’t hallucinate that congratulatory phone call or your benefits package.

And then… that first day you ask someone to pay you for the words you write for them.

These moments of fear didn’t precede traumatic downward spiral. (Well, at least not for most high schoolers…). These moments also didn’t mean that going to a new school, taking a new job, or taking a freelance client weren’t the right next step for you. It’s just a feeling. And fear isn’t the problem. The problem is how we respond to it.

Fear is not the problem. The problem is how we respond to it.

Freelance writing fear often sends the wrong message

It would be awesome if every good thing we ever did was accompanied by feelings of light-heartedness and certainty that would clearly say to us, “Yes! Do it! This is it!” But that’s not how our guts work.

Fear is really helpful in the jungle when it tells us to hide in the cave and be wary of those scary sounds. But when we’re trying to build a freelance writing business, fear is just a chemical process that comes along with something new.

It’s not foretelling the future.

It’s not a sign you’re doing the wrong thing.

It’s just a feeling — like hunger or sadness or a charley horse– that tells you something big is about to happen.

When we interpret fear as a warning sign that we should stop, we miss out on a lot of great things.

Some of us might not be married.

Some of us might not have children.

Certainly none of us would run freelance writing businesses.

But deep within each of these tough, wonderful, and intimidating-at-first things is a powerful desire that pulls us through the freelance writing fear and toward a new idea.

Don’t try to escape your fear — work with it

Eileen and I both had the same first instinct: run away from the fear. Run away and do something that won’t make those feelings come up. But that’s not a smart move for Eileen, me, or you, because here’s the biggest secret of all:

Successful freelance writers aren’t people who never experience fear. Successful freelance writers are people who understand that fear is a natural byproduct of doing good work — and that confidence is the result of that good work.

Successful freelance writers work side by side with fear to get things done, and at the end of the day they take their fear home with them to dinner.

Successful people aren’t people who never experience fear. Successful people are people who understand that fear is a natural byproduct of doing good work.

If you’re reading this, your story is probably a lot like mine.

You’re a good, solid writer. You know your way around a Word Document and you know that what you do is valuable to your clients. But when you go to pitch, or when you think of writing something for the business world, your throat clinches up a little and you get a bad case of the willies. You just aren’t confident that you’re worth those rates.

Well, some people let those fears stop them. But you and Eileen and me, we’re going to accept those freelance writing fears, scoop them into a little woven basket on our desk, and put on a show for our fear to watch as we try new things, pitch new clients, and turn in draft after draft of our best work.

Put fear in its place

Let’s look at the freelance life with new eyes. The fear you’re feeling isn’t always a sign you shouldn’t be doing this. It’s a sign that there’s something big there if you’re persistent enough to push through your first fluttering doubts.

Keep your eyes out for moments in your freelance journey that cause you to feel fear. Then, don’t run. Look the fear in the face and let it know that you appreciate its input… and that you’ve got some work to do anyway.

P.S. If you’re trying to overcome fears related to breaking into B2B writing, I’ve got just the thing for you: The B2B Booster Shot. If you’re trying to overcome fears about being productive as a freelancer with a chronic illness (or a baby at home, or whatever else you’ve got going on, this post is for you.

Is Your Brain Ready to Transition Into Full-Time Freelancing?

May 27, 2016 By FiveFigureSarah

When you guys pitched in to fill out my survey last month, I was super excited to respond to 30+ individual and interesting questions. One thing that really jumped out was the fact that much of the Five Figure Writer audience wants to transition into full-time freelancing, but hasn’t made the leap yet. In fact, about 75% of you guys are patiently biding your time, filling up your savings accounts, and picking up clients on the side.

(If you want to take the survey, sign up for the mailing list here and you’ll get a link to it).

There’s no shame in that! In fact, it’s the smartest way to do it. Plenty of people start freelancing as an emergency (that was my story) but it’s far, far better to have that runway time to save money, find clients, and generally not be frantic about your business.

So, for all you cube-dwellers building up your writing business on the side, here are five things you can do now to ease that transition:

Get your budget together & save a bunch of money

Let’s get the boring advice out of the way first: budgets and savings accounts are a freelancer’s best friend. I can’t say it clearly enough: cash flow kills 25 percent of small businesses early on. If you don’t get a grip on your spending or build up a bit of a cushion in the bank, freelancing will make you absolutely miserable and you’ll probably end up back in a cubicle.

If you don’t get a grip on your spending or build up a bit of a cushion in the bank, freelancing will make you absolutely miserable.

There are many ways to start tinkering with your finances before you transition into full-time freelance. I prefer the Dave Ramsey Financial Peace Plan and EveryDollar app, which helped my husband and I figure out a bare bones budget, organize and minimize our outgoing expenses, and save up $6K for a safety net (note: technically this is out of order of the FPU plan, but it was a necessary departure for the health of my business). You might enjoy a different finance guru or program, but it’s vital that you actually find one and use it to guide your decisions before you’re broke and waiting on a client’s check.

Financial stability (not necessarily security, which is a long-term concept) is about more than freaking out over late checks. It’s also about your attitude and your sense of desperation when you pitch new clients. If you have three or four month’s of expenses in the bank (and low expenses, at that) you can take your time with clients and make sure it’s a good fit and a good rate instead of jumping on low-paying work because your rent is due.

Embrace a farmer’s schedule (AKA 100% 24/7 is a myth)

One thing non-freelancers seem to assume about quitting their day job is that the transition into full-time freelancing means you’ll suddenly wake up filled with ~~caffeine~~ energy every day, ready to give your best to every client, crank out words, send newsletters, be on Twitter, and all that jazz.

In reality — and I wish someone had passed this along sooner — everything about freelancing goes in cycles. Much like a farmer, there are times of reaping and there are times of sowing. There are low income months and high income months, low referral times and high referral times, and, yes, there are low energy months and high energy months.

Everything about freelancing goes in cycles — there are times of reaping and there are times of sowing.

When you are tired and burnt out during your hustle, take it as a sign to take a break, not crank it out, so that you can get a feel for what it’s like to have cycles of high productivity and low productivity.

Start living by the phrase, “A man has as much luck as he has seeds in the field,” and practicing the art of reaping and sowing: write emails to people just to make connections, not to ask for any favors. Follow people on Twitter just for fun, not for business. And write things (and work with people) to spark creativity, not to build up your client list or land gigs.

Understand that confidence is a result, not a cause

Hands down the most popular topic, question, or concern in the survey was about confidence: How do I charge someone? How do I get my first gig when I’m not sure what I’m doing? Who’s going to hire me just because I want to write?

Listen, I had the exact same darn questions when I first got started. I was unprepared but dreadfully curious about how people got into this freelancing thing. And then I got laid off, and you know what? I wasn’t curious any more, I was desperate, so I just made it happen.

This is so, so important to understand: confidence is a result of doing good work and having good customer interactions. It is not a cause of those things. If you wait until you feel confident to pitch that client, send that email, send that proposal, or send that invoice, you will never. get. anything. done.

Confidence is a result of doing good work and having good customer interactions. It is not a cause of those things.

Is it scary and weird to start charging people money for something you love to do? Yes, at first. But once you do it for a while you start to build up that confidence that takes you to the next level, and the next, and the next. But if you don’t step up without confidence (and with fear and butterflies and maybe even some grasshoppers in your stomach), you’ll never reach the point of having actual confidence.

Find something bigger than money

There’s no denying that money is a big motivator for freelancers. Like I said in the budget section, cash flow can make or break your business, so income will always be a sign of the viability of what you’re doing. But despite your dreams of rolling in the dough and taking on a housekeeper or private chef, money only takes you so far in the freelance game.

I started this wanting to prove I was worth more than a $50K salary, and I did that. But pretty quickly after achieving that income goal (as well as earning five figures in a month), I lost my gusto again. I learned pretty quickly that beyond a certain ego factor, money isn’t enough to get me out of bed every morning.

Money isn’t enough to get you out of bed in the morning, and it’s not a compelling reason for people to work with you.

Money also isn’t a compelling reason for people to work with you. Think of hiring a lawyer or doctor for a huge moment in your life. Who would be more attractive, the one who got into it for the money, or the one who got into because they realized law/medicine was their ultimate calling and they find themselves renewed with every client or patient they help? Money doesn’t inspire others to join your cause or support your mission; you need a bigger “why” to make your business attractive to you and your clients year after year.

Accept “what you like” as a calling, not a fluke

As you try out different forms of writing as a part-time freelancer, keep your eyes peeled for what you actually like to do. Don’t punish yourself and assume that whatever you hate most is what will make you the most money — that’s a false value you’re bringing with you from the traditional working world, where the crappiest jobs often get the highest paycheck. It will also completely drain the life out of you.

For example, I spent more time than I want to admit thinking I had to write high-volume SEO blog posts and deliver social media strategy instead of white papers. Three years in, I’m finally unashamedly making white papers my specialty, and I won’t touch social media with a 10-foot pole (except for myself, of course). It took time to understand that some writers love social media and I hate it, and some writers don’t like writing white papers, and I happen to love it. These aren’t flukes — they’re signs that propel us toward our best work.

When something comes easily to you and you love it, don’t dismiss it.

When something comes easily to you, don’t dismiss it. If you love something, it’s not necessarily because the thing is awesome, it’s because you love it and you’re meant to do it. We all have unique talents and interest. You owe it to the freelance community to think about what you really, really love and focus on it.

What freaks you out about the transition into full-time freelancing?

These are just five of the lessons I’ve learned in almost three years of exclusive freelancing that would have been very helpful to learn early on. What other questions do you have for me about making the transition?