Solopreneur Survival: The 5 Scariest Things About Working Alone (and How to Control Them)

By Laura Gayle, Business Woman Guide

You’re ready to go out on your own as a solopreneur, and you’ve got major butterflies in your stomach. Who could blame you? This decision is a huge one and can be scary if you aren’t careful. There are so many challenges that you’ll face, including the five below, that it can seem impossible to succeed. But it’s not! With some planning and proactivity, you can overcome these problems and become the success that you deserve.

Running Low on Motivation

Trying to stay motivated to complete your day-to-day tasks is hard enough when you’re employed by someone else. But when you’re your own boss, you’re going to find your energy flagging from time to time. And since you’re totally solo, you can’t take many days off! Thankfully, the Mayo Clinic outlined some of the easiest ways to stay motivated, which you can easily integrate into your lifestyle.

Start by setting goals that you know you can reach. Long-distance goals are essential, but you also need smaller ones that help you achieve the bigger picture. And, most importantly, try to make everything as fun as possible. If you’re genuinely enjoying your time as a solopreneur and having fun with it, you’re going to experience more success and stay as motivated as possible.

Doing Your Taxes

Nobody likes tax season, and few hate it more than solopreneurs. Unlike other businesses that have a broad base of income on which to draw for paying taxes, you’ll be paying taxes out of your own pocket. This situation can be frustrating and scary if you try to embark on it with no help. There are so many mistakes that one can make when doing taxes that, in the worst-case scenario, you might freeze up and struggle to get them done at all.

Thankfully, you don’t have to take this difficult step on your own. Instead, you can hire a professional tax firm to handle most of the difficult elements for you. And you can also consult tax-preparation apps online to help you get an idea of what to expect. Remember that, as a solopreneur, just about every element of your life can be used as a tax write-off in some way. So don’t hesitate to get smart — but stay legal! — with your returns.

Being Solely Responsible

People who go solo are going to find that they have to make all the big decisions for their business: Which computers and hardware to work from? Which software platforms to use? How to secure insurance and retirement benefits? Whom to consult for accounting, payroll, taxes, bookkeeping? How to safeguard client and company information? 

The answer to the last question is, happily, becoming a no-brainer: Cloud storage is becoming the standard solution for storing precious data that is both safe and easily accessible from almost anywhere with an internet connection. A safe spot in the cloud almost virtually ensures that you won’t run into info storage complications down the road.

Operations and logistics questions are sometimes easier to answer for solopreneurs. Often the harder part, in the face of so many potential pitfalls, is maintaining self-esteem. Remind yourself as often as possible that you’re an intelligent and skilled person who is working hard to become even more successful — you wouldn’t have gotten this far if you were anything else! 

Staying Afloat with Unreliable Income

Though you can make great money as a solopreneur once you get into the game, you’re also going to run into patches of low income. This situation can be a challenge to anybody — troubles with overhead costs, loss of security, or substandard benefits. However, you can overcome this problem if you’re clever about the ways you use your income.

Try to find ways to minimize your overhead costs, such as cutting back on office space you don’t need or reducing your travel expenses. And try to find inexpensive health insurance to keep yourself healthy while on the road. You may even want to consider moving to a less expensive city — such as Kansas City, for example, with its robust job market and low rents — to ensure that your income remains flexible and your overhead less demanding.

Being Lonely

Being a solopreneur is a thrilling and unforgettable adventure for most, but it can also be a lonely one. Taking advantage of industry groups, co-working spaces, chambers of commerce, local business meetups, and other business-related opportunities for networking can help you build a base of professional contacts and colleagues. 

The problem of loneliness and isolation can be farther-reaching, though, particularly if you travel a lot — and with a solo business, you almost certainly will, at least at first. Without a home base from which to operate, you might find you have a hard time meeting people outside of work. Thankfully, there are ways to expand your social network while traveling:

  • Hostels — Stay in these low-cost travel centers to not only save money but also meet unique people during your travels.
  • Day tours — Take a break and meet new people while visiting exciting areas in the city.
  • Night events — Sign up for a pub crawl, cooking class, or any other event that piques your interest, and meet a group of engaging and fun people while you’re doing it.
  • Couchsurfing apps — Meet people using the “hangout” function travel apps.

There are many simple activities that can help stave off some of the loneliness of being a solopreneur. However, you may also want to take steps to meet someone outside of work who’s interested in the same kind of lifestyle or activities as you — whether it’s sports, science, the arts, travel, or whatever. This kind of connection can help you beat loneliness (and focus on work during the hours it’s called for).

The many challenges of being a solopreneur aren’t impossible to overcome if you’re smart and persistent. With careful management of your time and energy, you can stay happy and focused, becoming a successful and satisfied person while on this life journey. So get out there and do it!