5 Solutions to Common Solopreneur Struggles

This post was created in partnership with bSolo and features responses from real members of the C&C community. bSolo makes quarterly taxes easy with automated savings and payments on your behalf.

If you’re self-employed, you know how rewarding it can be to work for yourself: You get to do the work you love, take on clients you enjoy working with, and set your own schedule. But, of course, there are also challenges to solopreneurship. We reached out to our Create & Cultivate Facebook community to find out some of our members’ biggest difficulties in working for themselves. Read on to discover a few solutions to the challenges of running a one-woman show.


Striking out on your own can be a scary process, especially without the support of HR, accounting, and marketing departments to back you up. “The weight of every decision seems 10x because I don’t have anyone to talk through the pros and cons with,” says Farah D., who owns a vegan bakery. “Trying to be good at everything all at once is a big struggle.”

Thanks to the internet, it’s easier than ever to be a solopreneur who works alone but doesn’t have to feel alone. Facebook groups and online communities (like our Create & Cultivate group!) offer a free place to bounce ideas around, ask for advice, and even build personal and professional relationships with other talented entrepreneurs. You can also consider working a day or two a week from a coworking space (many allow drop-ins and offer off-hours memberships at discounted rates). But it’s not just a matter of existing in these spaces—you have to be an active member who’s open to meeting new people and starting conversations, even when it’s uncomfortable. By putting yourself out there both IRL and on social, you’ll likely meet like-minded freelancers and solopreneurs who can be a valuable asset to your business.


Jucel M., a designer & illustrator, says her biggest self-employment struggle is budgeting for freelancer taxes. “I can invoice and keep track of my transactions, but [I need help] on how to translate that into filing my taxes.”

No doubt, taxes are a surprisingly large part of freelance life—especially those pesky quarterly payments. But with bSolo, you can sit back and let their automated service handle setting aside money and making payments for you. Here’s how it works:

  1. When a paycheck is deposited into your linked bank account, bSolo puts a portion of your paycheck in a special tax savings account.

  2. When federal and state quarterly tax deadlines approach, bSolo automatically sends payments from your tax savings account on your behalf.

  3. Change your mind? You’re in control of your savings at all times. You can withdraw, initiate transfers, and change your settings at any time.

  4. When April rolls around, you and your accountant can rest easy knowing bSolo has sent your quarterly payments on time and you’re ready to file your annual return as usual.


Entrepreneurs are known to hustle. But how do you know when it’s time to call it a night? “My biggest struggle is turning myself off from ‘work mode,’” says Sierra M., a digital strategist. “If I’m just hanging out, I figure I can work on some aspect of my business—why not? So I don’t really let myself relax.”

Sound familiar? It can be hard to turn your “work brain” off and chill out when you’re the only one keeping your business running. But in the name of wellness, it’s important to truly shut down every once in a while. We’re not saying you have to enact a rigid 9-to-5 schedule (although that works for some people!), but you can start with “I’m not going to open my laptop on Saturdays” and go from there. Remember that because you are your own boss, nobody is looking out for your health but yourself—take care of your body and mind! And if that doesn’t convince you, know that studies show work-life balance increases productivity and creativity, so you’re really doing yourself a favor by powering down for a bit.


Deciding when to bring on help can be one of the most stressful parts of running a business. “Growing beyond being a solopreneur is a big topic of conversation within my community,” says Kristen P., brand stylist & creative director. “When is the right time? What is the right first hire? Etc.”

Hire too early, and you’re likely wasting money on a salary for someone you don’t need. But hire too late, and you face a mountain of work you can’t accomplish to your own standards. So when is the golden window of time for hiring? Experts say you should only hire someone when you’re regularly turning down work, you’ve found a new revenue stream (and an addition to your team would make you money), or you don’t have time to focus on important business aspects like customer service or accounting.

If you’re not ready for full-time employees, try hiring a contractor for a single project and see how it goes. You’ll learn how to manage and delegate, your project will move forward, and you’ll get a glimpse into what it’ll be like to make your first hire.


You’ve built a business from the ground up. You’ve tackled finances. Your clients are happy. But how do you create an effective marketing strategy to keep revenue coming in? “My primary struggle is coming up with the best ways to show potential clients the value of what I provide,” says Brandi H., creative director.

To create a marketing plan, write down what you specialize in and who your dream clients might be. This will help hone your marketing strategy to bring in the type of business you’re vying for. Next, get started on the actual content—perhaps this is a blog, an elevator pitch, or a killer portfolio site. Your content will depend on your line of work.

Lastly, find the right space to share your work far and wide. This may be through writing for a publication, sharing your portfolio on career sites or in Facebook groups, being a guest on a podcast, speaking at an event, sending cold emails, or investing in a booth at a conference. Do your due diligence to find out which would be most profitable for your business and go forth confidently like the savvy solopreneur you are.