Solving The Biggest Challenges For Solopreneurs And Freelancers

Many of my clients decide they want to leave corporate life.

They dream of driving their careers on their own terms.

They want to dictate their own schedules.

Choose their clients and collaborators.

But they fear making this move for a few main reasons…

1. The hustle
   The constant selling, of sounding fake or putting yourself out there. All. The. Time. And the possibility that you may be bad at it. Talk about a one-two punch.

2. Loneliness
   Losing the camaraderie and energizing social interaction that’s baked into a corporate gig where you’re all focused on a common goal.

3. Infrastructure
   It’s all on you: the scheduling, the invoicing, the customer service, the marketing, the IT support—on top of the doing the actual thing you left your corporate job to do.

If you’ve already drawn definitive conclusions that these variables are not something you can figure out, you absolutely should stick with your corporate gig or find another one that’s better suited to you. There’s no reason to make a move to the solopreneur/freelance world only to continue to prove yourself wrong. Some self-awareness and self-acceptance goes a long way in making this choice.

On the other hand, if this is something you feel you’re meant to do—you’ve done the math as to how to make it possible and you’re open to being uncomfortable and making mistakes in the name of progress—I got you.

Here are a few ways to address each of these fears head on so you can create the career and the business that’s calling you:

1. The hustle
   When you’re selling something you believe with all your heart, something you’re proud to offer—I can tell you firsthand—it doesn’t feel like selling. That said, I recommend that anyone who doesn’t feel comfortable about their sales and marketing skills get some support. Choose a few books you will commit to reading from this list of 50 incredible books. Read anything Seth Godin including his blog. Know that sales need not be a skill you’re born with, but rather a muscle you can build. You’ll learn that when you pour over Carol Dweck’s Mindset. If you can be kind to yourself, acknowledge where you need to grow and make friends with the experts—this is all possible for you.

2. Loneliness
   This was a tough one for me as it is for many of my extroverted clients. If you get energy from connecting and collaborating with others, you must build this into your days to stay afloat. I do this by working at co-working spaces via companies like Croissant, Spacious or Deskpass. Also, I work with affiliates—larger coaching organizations where I can find communities of other coaches to refer, to collaborate with on projects or to go out for happy hours. If you work from home, make sure you leave at least once to go for a walk or grab lunch with a friend. Instead of getting in that extra hour of emails, prioritize an energizing gathering that will leave you more productive for the rest of your day.

3. Infrastructure
   Here’s the good news: there’s never been a better time to start a business. Even if you’re a company of one employee, you don’t need to do everything yourself! There are apps and tools to get you up and running quickly for scheduling, accounting, email marketing—whatever you need. You can see my favorites here. Also, there are other entrepreneurs whose expertise matches squarely with the things you DO NOT want to do. Whether it’s technical support, social media marketing, copyediting or design—there are people who can help you by either bartering services or providing affordable packages for solopreneurs like you. You can find them on Upwork, Fiverr and by asking other entrepreneurs who already get the importance of delegation. This must all feel quite meta to my copyeditor of 2.5 years (thank you!).

   The truth is, while starting my own business was the best decision I ever made and the right choice for me, it absolutely can be tough. That’s why the answer I come back to over and over again as challenges arise is my mission, my reason for doing the work that I do. Above all of the logistical solves I offer here to address the "how" of running a business; the "why" is what pulls my clients and me through the plateaus and through the depths. The possibility of gender equity and gender parity is my fuel. This isn’t just about me, it’s about the increasing number of lives I can impact if I keep going, so I always find a way to do so.

Saying A Proper Goodbye

June for working parents. Need I say more? It’s laughable what we’re trying to pull off. White-boarding and logistics planning can make you feel prepared for that one moment, until the next picnic or recital is announced for…tomorrow.

This year, I’ve been swept up in the swirl of end of year busyness as I always am, and yet this time, there’s a dull ache just beneath the surface. While my go-to approach is to stuff it down further with more details to wrangle, it body checks me. Leaves me raw.

I become "that parent" sobbing during the class slide show, hanging on every handwritten note in the yearbook and searing the image of my two daughters walking to school together holding hands in my mind as if it’s already gone. Because it nearly is gone.

This week, my daughter’s six-year journey from Kindergarten to 5th grade comes to a close and while I want to shove it into that category of, "I’m not that special. Millions of parents have gone through this milestone before us." With respect and compassion, I also acknowledge that while I may not be special or unique on this front, I am human. And for humans, a change and a passage of time of this magnitude hurts. A lot.

All at once, there’s gratitude for teachers who guided and inspired, appreciation for a community of parents that I didn’t always know well, but made my mornings and field trips even more fun and interesting—and at the heart of it—there’s my kid who went from a curious, all-in little one to a still curious, capable person. Her growth has been dramatic and yet the qualities that we celebrated in her the first day she entered that school are alive and well.

Parenting—and childhood—for that matter is messy. Success only comes when we choose to honor our wins and acknowledge the gravity of goodbye. To do this I know I must:

Hang up my whiteboard marker.

Be there, be present for my daughter each time she asks, even if it’s to look at her final math project, one last time.

Look right at her, smiling and ugly crying during graduation even if it embarrasses the shit out of her.

A proper goodbye for me in this moment is a contract that says, this time and who you’ve become is the most important thing to me right now. It says that every exciting change has a loss attached to it—and feeling the grief right now is the only bridge to get to the other side.

My Most Efficient Moments Look Like This

As a business owner and a working mother, there’s a lot to do. It’s endless, really. During the busy times and the rainy weather, the first things to fall off the list are exercise and fresh air breaks. Apparently, I’m not alone in these self-care fails. That’s why last month when my mastermind group of small business owners was planning our June meeting, we decided to schedule a walk and talk in Prospect Park. While we didn’t break a sweat, we did get some steps in, enjoy the energy of the beautiful day, celebrate wins and plot out our goals for the coming months.

For me, these are the moments where I know I can focus on the things that are important to me and I can make the less fun parts of being a grownup fun, in my own way.

Listening to my favorite podcast while I pay bills and do my weekly budgeting tasks.

Rallying my daughters to help me cut out colorful quotes for my next workshop.

Setting up running dates with friends instead of dinners where we will both inevitably eat and spend too much.

This may sound like an obvious concept, yet I find in my coaching practice that suggestions to combine activities can have a profound impact in cleaning up procrastination and reigniting self-care.

To take this approach from idea to practice, follow these simple steps:

1. Make a list of tasks or activities where you’ve been stalling on forward movement or creating a habit.

2. Make a list of activities that feel like a treat or a gift—things you may feel guilty spending time on when there are "important things" that need to be done.

3. Match up tasks from each list so that they seem like a good fit in terms of duration, concentration level and focus. (Hint: listening to an audio book while performing a task that requires focus—like writing—will not work, but an audio book while folding laundry may be a perfect fit.)

4. Pick one or two to begin an efficiency experiment.

For some of my activity combos, I’ve started to look forward to the things I used to truly dislike. Like on the days when I have a 45-minute (or longer commute), I think—it’s just you and me, Terry Gross or Krista Tippett or Oprah. We’re going to make all of these delays and invasions of personal space memorable, even inspiring. And for those areas where I’m still procrastinating, I’m constantly asking, "How can I make this more palatable…or dare I say, fun?" Sometimes the answer is as simple as planting myself at my favorite coffee shop, brainstorming with a close friend or co-working with my puppy who rests his chin on my foot. Somehow, the joy of sweetening the deal gives me the fuel I need to keep moving forward.

The Power Of Appreciation

A few weeks ago, I attended a gathering at our elementary school with parents whose kids will be going to middle school with my daughter. I was not surprised to learn that the event, along with many others of its kind, was organized by our school’s Parent Coordinator.

Amidst the bustle of parent conversations about sixth graders riding the subway by themselves and gatherings to get the kids ready, I made sure to sneak away to chat with the Parent Coordinator who brought us all together. Feeling lucky to find her alone, I seized my moment.

"I’ve been wanting to thank you for all you’ve done for us through this entire middle school process. You held our hands to help us simplify when it all seemed overwhelming. You shared resources and parent stories so that we felt informed. And—most importantly, you created ways for us to connect with each other, so we can form communities as we step into this new and uncertain time. I felt supported each step of the way. You’re so good at what you do."

She was shocked by this outpouring of gratitude. In a year fraught with concerns and parent stress—there weren’t a lot of thank you’s flying around. And in this moment, I realized—yet again—how much we all need to hear these words. How they lift us up from our hard work, refuel us and help us redouble our efforts.

Here are a few tips to keep in mind as you step into this practice:

Offering appreciation
1. Maintain eye contact so this person can truly connect and take in your words.

2. Be specific! This helps the other person know what they can recreate next time. Note: it can be something small that made an impact.

3. Keep it positive. This is not a feedback session. It’s a time to offer thanks. You don’t want them to walk away focusing on that one negative thing you said—which is what we as humans do!

Receiving appreciation
1. Take it in. Own it. Don’t deflect and take yourself down a notch. This doesn’t feel good for you or the person appreciating you. This takes time to practice, but it’s worth doing! A simple, "I appreciate you saying that." is more powerful than, "It was nothing." Or, "It’s my job."

2. Let it linger. When you’re laser focused on the things you need to do better, remember the thank you’s that have come your way. Let them remind you of the impact you’re having on others.

3. Note the feeling of being appreciated and pay it forward. Catch someone doing something well and jump in with some words of encouragement.

I’ve noticed that often I find it easier to dole out that appreciation when it’s someone outside of my inner circle who has done the bang-up job. For most of us, our teams, friends and families are hungry for that acknowledgement. It may be that we take our close-in people for granted or that our expectations are so high, perhaps too high. Whatever it is, let’s collectively be reminded that this practice is doubly effective when used with our people. They are better when they hear words of encouragement and we are better when we are generous enough to offer them.