Mom Bossing: How the Rules of Productivity & Online Work Change with Parenthood

I started my first online business in 2010, when I was a college student still scraping my way through school.

By 2015 I felt like I had gotten the hang of this online business,freelancing, and blogging thing. So I started Unsettle.

I wrote about things like productivity — why you need to set a schedule, engineer your environment, find what works and do more of it, and sometimes, take some serious risk to get where you want to go.

Those things still work, for most people.

But they don’t always work for me, or another small but mighty portion of the online entrepreneur population:

The new parent.

As a new mom of a 6-month old preemie, online business owner, content marketer and digital nomad, these are the lessons I’ve learned being pregnant with, delivering and raising a baby.

Lesson #1: Babies Are The Best Kept Productivity Secret

I’ve had a few people tell me that they fear becoming a parent will give them less time to work on their businesses.

To that, I’d say it’s true.

Between feeds and appointments and entertaining your little one, you have a lot less free time to build your side hustle or grow your empire.

But the time you do have you’ll spend far more productively.

I noticed this before I had Poppy with my coaching clients. My clients who are parents are bosses. They accomplish more in a single day than I used to in an entire week.

People like…

  • Tracy, one of my favorite clients and Unsettler from way back when, who has a day job, a 3 year old, a busy travel schedule and still has managed to grow her blog into an incredibly popular authority site on natural parenting.
  • Margot, another one of my favorite clients, who started her ecommerce business in 2016 when her son was still new, and has built it into an empire that has allowed her to quit her job and start a clothing manufacturing branch in the Philippines.

I have many theories as to why having families seem to spark so much effectiveness, but there are two main reasons:

  1. Higher stakes. A few years ago, I quit my job in corporate HR to pursue my blog and freelancing full time from anywhere I pleased. That was easily one of the best decisions I’ve ever made, but the stakes were not very high. I could have failed and been fine. But now, I can’t fail. The stakes are higher. So I work.
  2. Constraints. I used to have all day every day to write an article if I had a deadline. Now, I have to get my work done during the day otherwise I don’t get to spend time with my daughter.

Babies are the best kept productivity secret I’ve ever seen…

Just don’t do something stupid like have a baby just to become more productive 😉

How to Make it Work

I’m convinced that one of the reasons babies are such amazing productivity secrets is because they add accountability.

Think about it: when your boss or a client has given you a deadline, you meet it. Right?

It’s no different with your baby. You have multiple deadlines to hit throughout the day – one nap can mean you have 1 hour or less to finish an article, send pitches, or meet a deadline.

Do this to make sure you hit those deadlines and avoid getting sidetracked:

1) Get an accountability partner. Having an accountability partner skyrocketed my productivity when I started Unsettle. Our quick check-ins gave me the extra push I needed to show up and get the work done, otherwise I would 1) appear uncommitted to my work and 2) have to pay a penalty we negotiated in advance. I didn’t want either of those things, so I got shit done. Even if you feel intimidated to reach out to someone, don’t skip this step. Finding an accountability partner is productivity magic:

  • Fantastic accountability partners and where to find them: The first step is identifying your ideal partner. Remember that an accountability partner is someone who shares similar goals and is in a similar position as you, so look for them in places you would hang out:
  • Facebook groups in your niche. FB groups are ideal for beginners. If you don’t have an online network or belong to any groups yet, this is the place to start.
      • Search and join groups in your specific niche. Type your niche in the search bar, select “Groups”, and ask to join the top results.
      • The influencers you follow online might have their own private FB groups, and here’s where you’ll find engaged communities filled with ambitious people who have similar goals and obstacles as you. Don’t forget to join other unsettlers at the Unsettle FB group 😉
      • Get active in the groups. Ask questions, respond to other people’s posts, and contribute positively so you can get to know the members in the group. They’ll probably have the same questions and challenges as you.
      • Groups from online courses. If you’ve ever bought an online course, you already have access to a like-minded community. Your fellow course takers share some of your challenges and objectives,so they would be perfect accountability partners. Most courses have a dedicated FB group where you can talk to other members.
  • Instagram communities. Connecting with people through Instagram is easier than you think. If you are focusing your efforts on IG and posting on a constant basis, this is a great place to find other creators and entrepreneurs, even if you don’t have many followers.
      • Search community-related hashtags. For example, let’s say you’re in the photography space. You would search for #photographersofinstagram #photographerslife and #photographytips
      • Click the top photos and check the account of each photographer.
      • Look for two things in each account: a style you like and similar follower size.
      • Follow the accounts that fit this criteria and start interacting with them. Like their posts, comment, and respond to their stories. They will notice and do the same for you. From here you can start a genuine conversation through DMs and become friends.
      • Alternatively, you can also find these accounts in the comments of influencers’ photos. Go through the comments of your favorite IG accounts and you’ll find smaller but cool accounts just like yours.
  • Reach out: Now that you are part of engaged communities, reach out to someone you you’d like to partner up with. Use and tweak this script as need:

Script: Finding an accountability partner

Hi [Name],

My name is [Your Name] and I’m a fellow member of the Unsettle private Facebook group.

I set a goal for myself to achieve [Your Goal]. I noticed that we both have very similar goals so I decided to reach out to you. I’m looking for someone to keep me accountable. This would include weekly 30-minute check-in calls to make sure we’re both on track to reach our goals.

Would you be interested in being accountability partners? If so, I’m available for our first accountability call:

Tuesday, after 7pm EST

Thursday, between 5pm and 8pm EST

Sunday, any time after 2pm EST

Thanks,

[Your Name]

  • Set up a schedule: If you both agree to partner up, set up a check-in schedule. I recommend you check in twice a day – in the morning to tell each other your daily goals, and in the evening to talk about your progress. You can use any platform you like – Skype, Slack, Facebook, etc. It’s important you stick to your check-in schedule so neither of you falls of the wagon. Speaking of sticking to something…

2) Use Stickk or another goal-setting platform to help increase the stakes. Stickk lets you set a specific goal along with a monetary penalty if you don’t do what it takes to achieve that goal.
The pressure of losing money lights a bigger fire under your belly to do whatever it takes to crush your objectives. Use this app with your accountability partner to raise the bar.

  • First, create an account on Stickk. Then…
  • Set your goal. Let’s say you want to grow your photography biz in the next 6 months:
  • Add the specifics. What will you do to reach that goal? How long will it take? When will you start? When will you report to your partner?
  • Choose your punishment for not sticking to your goal. You have several options:
    • Donating to an anti-charity: This option sends your money to a charity that goes against your values.
    • Donating to a charity: Stickk sends your money away to a random (good) charity.
    • Sending money to an enemy.
    • Sending money to a friend.
    • No money involved (don’t take the easy route with this option though!)
  • Optional: Add a referee. You have the option to add a third party that will verify you’re sticking to your agreement, but it’s not necessary.
  • Add your partner. The final step is to add your partner on Stickk.

Now that you and your partner know each other’s goals, created a check-in schedule, and raised the stakes, you can start pushing each other to smash those goals.

Ready to skyrocket your productivity? Click here to download the accountability partner agreement, along with all my SOPs + worksheets in a super handy swipe file.

Lesson #2: Deep Work Only Works When You’re Not on Baby Duty

When I was pregnant, I read the book Deep Work by Cal Newport.

It’s one of the best productivity books I’ve ever read, about ruthlessly cutting out all distractions to focus on “deep work” – the important stuff.

Deep work is a seriously crucial aspect of productivity, but I cringe at my previous self, who would say blanket statements like…

“If you’re really committed you’ll wake up earlier and do the work”

and

“If you let yourself get distracted when you’re in flow, you’re not serious”.

These blanket statements don’t apply to everyone.

I’m sitting here working on a Saturday afternoon, my baby wrapped like a burrito next to me on the couch. I periodically make sure that she’s breathing, because she’s sleeping and has been for a couple of hours, a rare long afternoon nap.

But every once in awhile, she begins to stir and my focus breaks.

That task-switching thing I’m always ragging on my clients to stop? That’s become the norm, at least in this work session and any work session I do while I’m on baby duty.

How to Make it Work

Studies show that scheduling your tasks makes you 3x times more likely to follow through than just winging it. In one study, researchers measured the effects of motivation on exercise. They compared the difference between motivation alone vs motivation + intention (planning). Here’s what they found:

  • The Control Group was instructed to keep track of how often they exercised over the course of two weeks, and given a few lines of a neutral book to read. The results: 38% of participants exercised.
  • Group A (Motivation) was also instructed to keep track of exercise frequency, but instead of reading the portion of the neutral novel, they were told to read a pamphlet outlining the benefits of exercise on heart disease risk. The result: 35% of subjects exercised.
  • Group B (Intention) was treated the same as the Motivation group, except for one thing: they were also asked to set a schedule for when they would get exercise over the course of the two weeks, as well as how long the workout would be and where it would take place. The result? An impressive 91% of participants exercised.

The study concluded that setting an intention allowed people to delegate control of their behaviour to the environmental cues (their schedule), so when they see their schedule, it triggers an automatic behaviour.

In other words, the decision to exercise was pre-made, so they didn’t struggle with it when the time came.

You will be more effective if you plan your future decisions and actions, instead of depending on your fleeting motivation every time you have to get something done.

The best thing you can do for your business right now is to set a clear plan of attack. It will let you make the most out of your shorter work hours.

There are two ways you can make it work:

  1. Schedule and have your partner watch the baby. If you’re the primary caretaker, this might mean you have to work in the evening when your partner gets home from work. It sucks, but it works.
  2. Work during your baby’s naps. This will not be possible during certain periods of your baby’s babyhood. When kiddo is a very new newborn, she’ll sleep around the clock, but you’ll either be adjusting to having a new baby or recovering from pushing that baby out, so it’s not realistic to tell you that you’ll be able to get much done in that time period. When Poppy turned around 4 months old, she began taking longer naps twice a day though, which allowed Ryan to put more time into Adventure Baby.

Lesson #3: My “Why” Has Completely Changed

When I quit the corporate rat race in 2014, lifestyle design was my main MO.

The goal? To be able to travel whenever I wanted, without asking for permission from a “boss” and fight for three weeks of vacation each year.

Now, lifestyle design is still the main reason behind why I love working online, but the goal is different.

Not only do I have to make sure that I’m, you know, providing for my family (I’m the primary breadwinner right now as Ryan’s on parental leave), it’s incredibly important Poppy to see me handling it.

I’m not going to pretend it’s all sunshine and rainbows, because that won’t serve her.

But I do want my daughter to not only know that she has options, but see us as an example of the ability to pursue those options.

Robust research shows that children of working mothers:

“Completed more years of education, were more likely to be employed and in supervisory roles and earned higher income”.

I want Poppy to see me working hard in a career and business that I love. I want her to know she doesn’t have to lose herself in her family (if she chooses to have one). And I want her to have the confidence to pursue the life she wants, too.

My “why” has evolved so drastically in the 5 short months she’s been my baby.

How to Make it Work

“Working hard for something we don’t care about is called stress; working hard for something we love is called passion.” – Simon Sinek

The “why” behind the mission of your business is less important than why you have a business.

Having a business is no longer only about padding my savings account or earning the freedom to work wherever I want.

Those things are still important, but being the role model my daughter deserves has become much more important.

Here are a few ways to “find your why” and use it as a motivating factor to keep going:

Step 1: Do the Perfect Day exercise

First, grab a pen and piece of paper.

Now, close your eyes and picture the perfect day. Picture it in insane detail. If you woke up tomorrow in your perfect life, what would that look like?

Think about:

  • What time you'd wake up
  • Where you are (country, city, physical location)
  • What type of place you'd live in (money being no object)
  • Who you would wake up next to
  • What you'd do when you first woke up
  • What you'd eat
  • What you’d wear
  • Who you'd interact with
  • The type of work you'd do
  • What you'd do for fun
  • What your schedule would look like for the day
  • The skills you’d have
  • How much time you’d spend with your baby

When you open your eyes and you have a good grasp of what your perfect day looks like, write it down. There are three reasons this is a great exercise:

  1. Knowing what your perfect day looks like helps you make it become a reality.

Daydreaming about your perfect day will make your vision crystal clear. You’ll uncover your true motivation – your why -, and you’ll know exactly what to pursue.

  1. This exercise is not only the destination, but the roadmap.

When you have your vision of your perfect day, it acts as a roadmap for all of your decisions.

You can use it to filter every choice you make from now on.

If an “opportunity” crops up that you need to make a decision about, whether you take it depends on whether it helps you reach that perfect day, or whether the you in that perfect day would take the opportunity.

  1. You'll get a renewed sense of your priorities and interests

When I did this exercise, in my daydream I woke up in a mid-sized house near the lake. I had never really defined my ideal home before, but that made it very clear to me that my priorities did not lie with having a mansion or a condo in the city.

The work I was doing in my daydream was work that allowed me to be location independent, work in a home office and give me the flexibility to make my own hours.

Digging deep into what you truly want will make your priorities obvious, and make it easier to let go of anything that doesn’t fit your vision.

Hint: The last time I did this, it was 2 years ago and now I’m living almost the exact life that I pictured in my perfect day. #winning

For instance, if you want to run a successful consulting business that lets you move to a new country with your family within a year, you’d focus your energy on building that biz and researching about your dream country, instead of remodeling your home or applying for a new job.

Step 2: Dip your feet

Unearth your why by taking action.

In his book Man’s Search for Meaning, Viktor E. Frankl wrote there are three ways to find your meaning:

“(1) by creating a work or doing a deed; (2) by experiencing something or encountering someone; and (3) by the attitude we take toward unavoidable suffering”

Acting out at least a tiny part of your perfect day will create an emotional attachment to your why that you can’t get just by thinking about it.

  • If you want to move to Bali with your family, go there on a family vacation for a week.
  • If you want to trade your apartment for a boat and sail for months, rent a boat for a weekend and sail.
  • If you want to live off your art so you can spend all the time in the world at home with your baby, start working on a print you are determined to sell, or set up a website for your existing art.

You can test the lifestyle of your dreams at a small scale. This will help you crystallize your why and motivate you through the hardest of times.

Step 3: Remind yourself (constantly) of your why

It’s easy to lose your “why” while you’re trying to juggle your business and your baby, all while sleep deprived. Stay on track with constant reminders:

  • Download the Momentum Chrome extension and set your background as a photo of your why.
  • Use Hey Focus (productivity blocker app) when you’re trying to get things done. You can set your own quotes for if you try to pull up a page you’re not supposed to visit (for example, if you’re trying to write an article and you go to Facebook). Include a few quotes about your “why”, to remind you why you need to focus and get the work done.
  • Take breaks throughout the day to refocus. When you’re feeling overwhelmed, tired, or distracted, you have to break the pattern. Disconnect from your work for 30 minutes to breathe, take a walk, wash your face, stretch, make coffee, or call your partner. Do anything you can to improve your mood. When you are feeling better, think about your why to get motivated again.
  • Do a day review. At the end of each day, do a quick review of the progress you made. Write down everything you did that day and what you accomplished in your work, and determine if what you are doing is bringing you closer to your perfect day. Keeping track of your daily actions will make you accountable to yourself and help you refocus on the things that matter.

Get the Perfect Day exercise worksheet (plus all my SOPs) in my swipe file below:

Lesson #4: I’ll Always Have More Money Than Time

You can always make more money, but you can never make more time.

Ryan and I are doing what we can to challenge gender roles and stereotypes for the sake of our kid.

This means that instead of the primary caregiving role defaulting to me as the woman, we looked at:

  • Eligibility (I wasn’t eligible for Canada’s generous 8-month parental leave policy, Ryan was)
  • Income and earning potential
  • The research behind parental roles and breadwinning.

We determined that I would work (returning after a short maternity leave from Sumo) while Ryan took the parental leave to care for Poppy.

I’m incredibly lucky that I can grow my business, write for a company I love, and be a mom to the best baby on the planet while somebody I love and trust looks after her.

But here’s the thing…

Mom guilt doesn’t give a shit about my disdain for gender stereotypes.

There’s always something in the back of my mind, nagging me that I should be the one looking after Poppy. Telling me that I’m missing out and that I should be spending my time with her, not with Google Drive and Slack and WordPress.

When my friends who have babies get to go out during the day and enjoy their maternity leaves together, I have a pang in my heart.

When I overhear Ryan playing with Poppy in the middle of the day, my stomach clenches.

I used to be frugal because I believed I could afford the time to do so.

Now I realize that I have far more money than time, and I outsource literally everything besides content creation in my business.

That means that with Sumo + Unsettle, I’m doing only what I love and am good at and not spending time on the things that others can do better than me.

I don’t want to pull 80 hour work weeks to grow my business. I want to spend just enough time to do what I truly enjoy doing – writing – and spend the rest of my time with Ryan & Poppy.

And frankly it doesn’t matter how I spend that time as long as I’m spending it with them. It’s no longer work hard play hard. Now it’s work just hard enough and family-time hard.

The most worthwhile of times is when we’re doing very little. The other day, we had to do diaper laundry (Poppy’s in cloth diapers and your baby should be too) while we were hanging out in the Oregon Coast for a week.

I could have either stayed behind and let Ryan and Poppy go do the laundry while I got caught up on Unsettle email, or go with them. I chose to go with them and had such a blissfully fun time eating ice cream while playing with Poppy while we waited for our clothes to dry.

You can always earn more money. You can never get more time.

How to Make it Work

Okay, you need to hire somebody so you can focus on the important things in your business.

Check.

Here’s how.

1) Track all the processes and tasks in your business.

Write down everything you do in your business.

Instead of trying to remember everything you’re responsible for, track a couple of your days using a spreadsheet and identify all the tasks you do in your business (content creation, design, article promotion, responding to emails, social media management, email list management, landing pages, course creation, reaching out to influencers, etc). You want a full list of everything that keeps your business running. Then…

2) Figure out what only you can do vs. what you can outsource

Identify the essential business tasks only you can do, versus what you’re spending time on that:

    • Somebody else can either do,
    • Somebody else would be better at or
    • You could pay somebody less than your hourly rate to do it.

Get honest about what really moves the needle in your biz. What are those key things only you have the skills to do? Anything else that doesn’t fit into that criteria can get done by someone else.

If you try to do everything at once, you will limit your time and the quality of your output.

You are not being lazy or mediocre for outsourcing tasks, quite the opposite. You’ll free up time and brain space to focus on income generating activities, while everything else gets done just as good or even better than you expect.

3) Work out your hourly rate

How much is your time worth per hour? My average hourly rate is about $100/hour. Every time I’m doing something that I shouldn’t be doing (read: doing anything that isn’t creating content), I ask myself, would I pay a freelancer or VA $100/hour to do the same thing? If the answer is no, the funny thing is that I already am, by doing it myself.

Figure out your hourly rate so you can have a sense of how much you could pay someone else to take on your tasks.

Let’s say your rate is $50/hour. If you hire a VA for $10/hour (20% of your rate), you save $40/hour and can spend that time on tasks that increase your income.

4) Pull the trigger

Ultimately, you need to free up time to do what you do best in your business.

So many people fall into the trap of thinking that they can’t afford to hire anybody or outsource anything, because they’re not making a ton of money. After all, if you’re not exactly making bank in your business, how can you afford to pay somebody else to work in your business?

But if you’re not making bank, you can’t afford not to. You need to be focusing on revenue generating activities. You can’t waste your time doing the necessary but basic administrative tasks.

Do it like this:

  • Start small: Start by hiring somebody to take the most administrative tasks off of your plate, like uploading things into WordPress, setting up emails in your email service provider, creating social media images, and managing your calendar. On Upwork, you can find a decent VA for $10/hour or less. If you are extremely detailed in your instructions for them, you should have no problem with the quality of work. Starting off with a cheap VA will help you get a hang of how to manage other people, delegate tasks successfully, and feel the value of outsourcing.
  • Move up: As you begin to see the ROI of working with somebody, you can begin to level up and bring on more skilled contractors. A good VA who will take on tasks bigger than just basic paper pushing will cost at least $25/hour, but I’m not suggesting you jump right into paying $25/hour from the start. Look for experienced freelancers when you need help on more complex and sensitive business tasks like content creation and co-creation, implementing and tracking social media strategies, and brainstorming solutions.
  • Pass on the know-how: Record videos of you doing the tasks you want your VA to take on, and then show them the ropes.

Pro tip: Record video lessons for your VA easily in Mac or Windows like this…
For Mac users: Open Quicktime, click on File, and choose New Screen Recording from the dropdown menu. For Windows users: Download a free app like Bandicam. Open Bandicam, choose your prefered recording mode, and hit REC to start recording.

Want to get the screencasts and SOPs I sent to Unsettle’s project manager? Click here to get a swipe file with scheduling worksheets, SOPs, screencasts, and everything you need to onboard your new hire.

Lesson #5: The Lifestyle I’m Designing Looks a Little Different

Last year, I visited over 29 cities across 11 countries.

I didn’t have an address because the world was my home. My mail was sent to my mom’s house, and I’d get it every several months whenever I saw her.

Now, lifestyle design looks a bit different.

I’m not going to say you can’t travel with a baby. In fact, I spend a lot of time proving that you can travel with a baby.

But doing the whole “digital nomad” thing has changed.

I’m currently writing this from an AirBNB in Cape Meares in the Oregon coast, so don’t think I’ve completely thrown the towel in on traveling as a lifestyle. But now I do it with a not-so-healthy dose of mom-guilt.

Okay, so mom guilt. Check. But I’m still a digital nomad, right?

Well, sort of. Throughout my pregnancy I was anxious that I wouldn’t be able to travel when I became a mom.

I never knew that I wouldn’t want to travel as much.

Don’t get me wrong. I definitely still love travel. But I also love home.

I love lying on the floor of the nursery in Canada with a stuffed lion puppet on my hand, pretending the lion is eating Poppy’s toes.

I love waking up and going to a gym I have a membership to and getting a workout in before I start my work day in my home office.

And nothing feels better after traveling than coming home, sleeping in my own bed, and making dinner in my own kitchen after a long day of writing, editing, and trying to take over the internet.

How to Make it Work

Lifestyle design is all about designing the life that you want. Not trying to keep up with the life of your favorite Instagrammer or another family just because you think that’s what you should be doing.

This is where the perfect day exercise comes in again.

Go over your perfect day as vividly as possible whenever you need to recharge. Imagine how every aspect of your life would look like. What lifestyle would make you truly happy and content?

Decide travelling is part of your perfect day? It’s not so hard. Poppy went on her first flight when she was just a few months old. When she was 8 weeks old, we took her on a 3-state, 28 hour long road trip across several National Parks, cities, and monuments.

Travel looks a little different. But it’s still totally possible.

Mom Bossing Is Hard

Being a mom has made me so grateful for my business & for being able to work online. It’s made it so:

  • We can choose to raise Poppy wherever we want, rather than wherever we work
  • My earning potential is not limited by bureaucracy or the corporate pay scale
  • I don’t have to choose between my career, my sense of self, and my family.

It’s given me and my family options that I never would have had before.

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