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5 Struggles Every Solopreneur Understands (And How to Make Peace with Them)

5 Struggles Every Solopreneur Understands (And How to Make Peace with Them)

In my last post, I shared a number of benefits of being a solopreneur because, let’s face it, it has to be worth it or else I and all of the other solopreneurs out there wouldn’t likely take this type of career route.

However, no matter how much you like what you do for a living as a solopreneur, working for yourself and by yourself isn’t always easy. Especially if you truly care about your company and want a brand based on integrity, character, and always being willing to go the extra mile.

With this thought in mind, here are five struggles every solopreneur understands, as well as how to make peace with them.

Being Responsible for Ev-er-y-thing

One of the things I miss most about working with a team of people is, though we each had our own responsibilities, if one of us was overloaded, others were right there, willing to pitch in. Granted, this didn’t happen all that often, but it was nice always knowing in the back of my mind that help was always just one office away. Yet, as a solopreneur, that type of safety net goes away.

If all of your clients contact you at once, requesting your products or services, you’re either going to work super long days and ask for extended deadlines or you’re going to be turning down cash in the bank. There’s no one there saying, “Hey, I see you’re overwhelmed. Let me take care of that for you.” The one thing I do that helps me make deal with this sometimes stressful aspect of solopreneurship is that I don’t pack my schedule too tight.

If I think a project will take me two days, I’ll quote four. That way, if something happens that I didn’t expect—like getting sick, having to deal with a family emergency, or suddenly realizing that your dishwasher is spewing suds all over your kitchen floor (yes, this was me just a few weeks ago)—I don’t stress as much because I have time to deal with it without missing a deadline.

In addition to putting me more at ease, this also makes my clients happy because I generally deliver their content well before the deadline. Essentially, it’s the same premise as under-promising and over-delivering, a strategy that has helped me grow my client base to the point where I am now turning down some new clients because I simply don’t have any more time.

Not Having Someone Else to Bounce Ideas Off

I’ve talked to many solopreneurs who’ve shared that one thing they struggle with is not having someone else to bounce ideas off. There’s no one there screaming, “Wait! Don’t do that or you’ll be sorry!” And there’s also no one there saying, “Wow! That was a great idea to do that on that project. You rock!

Having another person to talk ideas over with—someone who can help you see things from a different perspective or who can see things you can’t—helps you stay on the straight and narrow with your business. It also reduces the amount of trial and error you have to go through because you have the added benefit of someone else’s wisdom. How do you deal with this aspect of solopreneurship?

One option is to find a mentor in your field who can serve this purpose for you without necessarily having an investment in your business. Reach out to someone you know who has seen success in areas you want to master. You can also reach out to someone you don’t know (maybe someone you’re connected with through LinkedIn or some other professional network) but would potentially be willing to give you a few moments of their time if you find yourself in need of another opinion.

Another alternative is to hire a business coach. This person can help talk you through whatever obstacles you feel are in your way, and work with you to develop strategies for overcoming them. This also gives you someone who will hold you accountable, which is great if you’re the type of person who needs a little push to get things done.

You can also join a group of professionals in your field, or a business group in general. I belonged to a mastermind of writers for a while and I learned an awful lot about what to do and what to not do when growing my business. It also enabled me to connect with a few other writers I know I could still contact today if I am struggling in an area and need some advice.

Spending a LOT of Time Alone

When your business consists of you and only you, you wind up spending a ton of time alone. This is good because it allows you to get your work done, but it can also leave you feeling like Tom Hanks in Castaway, your only friend a soccer ball that you’ve affectionately named “Wilson” and given its own personality.

The way I choose to overcome this is by having a noise source on almost all of the time. Right now, while typing up this article, I have the TV on in the background. Though I normally can’t even tell you what’s on because I’m not paying attention, just hearing other voices is enough to keep me from feeling the realities of being totally alone.

I also decided to join Toastmasters. Not only did this give me a reason to get out of the house every week, but it also helped me grow professionally by giving me the tools I needed to become a better public speaker—one of the latest areas I’ve been growing my business into.

Also, any time that I am out of the house, whether to get groceries or go for a walk, I make it a point to talk to those around me. I’ve met some very interesting people along the way by taking this approach, like the woman who was extremely excited about her new $2 bra or the man who shared that he’d just lost his wife and appreciated that I took the time to stop and chat.

Even though these interactions are generally only a couple of minutes at most, they’re typically enough to satisfy my need for social stimulation. This leaves me feeling much more content when I return to my solitary work.

If you’re struggling with the fact that working for yourself leaves you alone a lot, try one of these approaches. Join a group that meets once a week or so, forcing you to get out of the house every once in a while, or make small talk with those you meet in your everyday travels, satisfying that conversational itch.

You never know who you’ll wind up crossing paths with. One time, I went to the grocery store and met a psychologist who was willing to speak with me and help me with one of my articles. If we hadn’t struck up a conversation over lunch meat and sliced cheese, I never would have made that connection.

Pre- (and Post-) Vacation Work Surges

I remember my B.S. days (“Before Solopreneurship”). I used to really look forward to my time off because all I had to do was make sure someone was assigned to cover my work and I was good to go.

However, now that there is no one there who can do my work for me, getting ready for vacation typically means working from before sun up to after sun down the week before I’m away, ensuring that my clients content-related needs are covered while I’m gone.

Don’t get me wrong, I still look forward to my days off with my husband and other family, exploring new places or simply relaxing at home. It’s just that now that time off is preceded by super long days, and it’s generally the same when I return. My clients haven’t had my services for a week, so they’re ready for more content once I’m back, which means long days once again.

Certainly, I’m not complaining because I’ve worked extremely hard to build my business to the point where work is steady, eliminating the feast or famine situations I faced often in my first few years of working for myself. I’m simply saying that, as a solopreneur, you need to plan for these as best you can so you can keep your clients happy while still enjoying some much-needed downtime.

Typically, I let me clients know 1-2 months before I’m going to be off so they can get projects to me earlier, helping to avoid that last-minute rush. I also keep my schedule somewhat light the week before I’m going to be away, giving me the ability to fit in quick projects requested by clients before I leave.

I also know that my schedule will be pretty busy when I return, so I schedule that week lightly too. This gives me time to get back into the swing of work, while also enabling me to play with my schedule if I run into any issues that arose while I was away.

If your business is the same, giving yourself a little wiggle room right before your vacation and after your return can give you the time you need to deal with last minute or unexpected issues without having to wear yourself out completely before you go.

Never Really Being “Off Work”

A few weeks ago, I went overseas to visit family. Before I left, I told myself that, no matter how much I was tempted, I was not going to deal with any work-related communications. That lasted about two days.

Though I had my email set to auto-respond that I was out of the office, on my second night away, I got a message on social media. Certainly, the sender didn’t know I was away so I didn’t want to ignore it. However, even responding with, “I’m away right now, but I’ll get with you when I return!” still meant that I was dealing with work.

A couple days after that, I got an email questioning where my client needed to send my payment, since I had recently moved. So, while this person would have received my auto-response, if I waited until I got back to answer, that meant my payment would be delayed as well.

Now, your first thought is probably to question why I don’t hire a virtual assistant or someone who would be willing to do these things for me, at least while away. I probably could, but since it isn’t someone I need full-time, I have never really felt the need.

Plus, if I were being totally honest with myself, I could have let those things go until I returned. But my desire to always go above and beyond with my business usually wins out, and I wind up giving in. So, how do you deal with never really being off work?

I think the first step is to realize that this is just part of being a solopreneur. Especially if you’re a solopreneur like me who is a little bit of a perfectionist control freak.

Or you can do what I try to do once a year, and that is to go on a vacation where you don’t have internet access. When I do this, there’s no temptation to see what work is in my email inbox because it’s not even an option.

This enables me to truly get away, which also helps me come back feeling totally refreshed. And ready to do it all over again.


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by Christina DeBusk // Freelance writer, author, and small business consultant committed to helping entrepreneurs achieve higher levels of success.

Opinions expressed by contributors are their own.