What I’m Struggling With as a Solopreneur

One thing I’ve struggled with over the past few months is finding continued inspiration and motivation. As you can imagine, it’s hard sometimes being your own boss. There’s no one telling you what to do or when to do it. There’s no clear laid out path to success to follow, you have to pave your own way.

Ironically enough, most of the time this is what I actually LIKE about starting my own business and working for myself. I get to be creative and think outside the box. I decide what nights I work and what nights I relax or hang out with friends. I can focus on what I’m good at and outsource for the areas I struggle with.

This summer and fall, I felt like I was doing just enough to stay afloat. I wasn’t brainstorming or being creative or coming up with new ideas. I guess this is understandable, I’ve been so busy with the shoots I had that I didn’t have space to stop and think.

And then last Wednesday morning happened.


My alarm went off as usual at 5:30am, but this time I didn’t get up and run off to the gym. Instead I just laid there in bed starring at the ceiling, listening to the cars rush past my apartment and to the rain fall on my windowsill. Maybe it was because it was dark, cold and rainy, and I didn’t feel like going to the gym.. or maybe it was because I was finally listening to my heart and what it really needed.

For the next hour I just laid there and thought about my business. I imagined what I wanted it to be. I thought all the ways I could get there. All the things I wanted to do. And then it dawned on me: I hadn’t done this in months. I haven’t stopped to really think in months.

It felt so good to brainstorm and dream and make plans. To feel enthusiastic and passionate about what I was doing again.


Recently, Alexis Grant and Jessica Lawlor (two fellow entrepreneurs/bloggers) wrote posts about what they struggle (or struggled) with while growing their businesses and creating the life they want. I was inspired to join the conversation and share what I also have been struggling with lately. I don’t think I come off on this blog as someone who has it all together, but maybe I don’t show the struggle as often as I should in an effort to stay positive. So here we go.

Here’s what I’m struggling with right now.

Accepting I’m not there yet. I may know what I want my life to look life, but actually getting there takes time. And to be honest, I’m really far away from that picture I have in my head of my life. It requires a lot of patience and faith (every. single. day.) to trust that I will actually get there if I work hard enough.


Saying no. I want to say yes to every opportunity that comes my way. Every shoot, every blogger meetup, every client request, every volunteer opportunity, every social outing. This is partially because I’m a people pleaser and partially because I have the disillusioned belief that I can do it all. (Spoiler alert: I can’t.)

Unplugging. Since I run my photography business outside of working a full-time job, I’m working on weekends and weeknights all the time. I have no set schedule for when I work and when I don’t. I try to squeeze work in whenever I can: responding to emails on the way to the gym, designing an album while getting ready to meet up with friends.. but this means I never truly unplug.


Knowing what to do next. Unlike a typical job, there’s no one here telling me what the next step is. Should I invest my savings in a new lens or marketing tactics? Should I be spending more time on this blog or in person networking? I read tons of articles, I get advice from other successful photographers, I do my research: but I’ll just say it: sometimes I have NO IDEA.

Being too hard on myself. I’m doing the best I can with everything I have going on right now, deep down I know this.. but sometimes I beat myself up for not being a better friend, skipping the gym six days in a row (that happened last week), spending a night in front of the TV instead of doing work, etc.


Sleeping. I’ve been averaging about six hours of sleep a night recently. This isn’t because I’m up late working, either. This is because I can’t turn off my mind anymore, causing me to wake up at 3 or 4 am and be restless until my alarm goes off. I’m a classic overthinker, especially when I’m stressed.

Self doubt. Who am I to be starting my own business? … Do I have the personality that it takes to be a successful photographer? … Do I want this bad enough? ..This is a scary, dark place, my friends. And it creeps up when I’m least expecting it.


So there we have it. What are you struggling with right now?

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  • I love the honesty in this post. I feel all of these things about both my jobs (mom and teacher) even though they are very different jobs than what you are doing. Maybe everyone feels this way…ReplyCancel

  • I love honest posts like this as they are so relatable. I may not be starting my own business but in a way, my roll is entrepreneurial as I am building a business/reputation within my company and I have very little structure/guidance on what I should be doing so every day I have to come in and come up with ideas of what to write or how to impact the business and it’s hard/scary/difficult. Some days I just want a job with well-defined duties, but I also appreciate the freedom I have in my role.

    I have thought about doing a post like this as well as I sometimes wonder if people read my blog and think I have it all together because I don’t. Things I am struggling with lately are the increase in responsibility/pressure in my role, the lack of job security, comments people make about my relationship that makes me feel like they are rushing me to get engaged/married, sleeping (I’ve been awake since 3:30 so I feel you on the sleep thing!), saying no to things and not feeling guilty, and caring less about what others think of me.ReplyCancel

    • Caroline

      I think everyone is a little bit of an entrepreneur, whether they work for themselves or not. I hope you write one of these posts, it kind of feels good to just put it all out there!ReplyCancel

  • Nice job with this! And I love how you compared Jess’ post to mine — I hadn’t even realized we had written similar posts lately! What a great conversation to have… It’s easy to think the person next to you “has it all,” so I hope this sparks others to talk about what’s difficult for them, too.ReplyCancel

  • I know exactly how you feel girl!! Sometimes I look at the big time running bloggers and think how the heck did they do it??? I want to be successful in my running, blogging, and coaching but it is just so hard to know how to make it happen!

    You will get there though! Like you said it takes time and patience 🙂ReplyCancel

    • Caroline

      Thanks, Lauren! I definitely need to work on being patient haha 😉ReplyCancel

  • Thank you for being so honest and genuine as always! I don’t have my own business but would love to some day and can imagine it’s incredibly tough to turn it off when that’s your passion. I too haven’t made it a point to just sit and think enough lately and you’ve inspired me to *make* time!ReplyCancel

    • Caroline

      It’s so hard to rationalize making time to do nothing/sit in silence when we’re so busy but it’s always worth it!ReplyCancel

  • Hillary

    Really like this post. It’s so relate-able, whether or not you’re an entrepreneur or not. Self doubt, having faith that hard work will pay off, not taking a moment to really think… I feel like those are all themes of my mid-twenties. Wondering when that will slow down! But then again, if we weren’t having those thoughts.. would we just be stagnant/complacent?ReplyCancel

    • Caroline

      I think about this a lot actually! The line between wanting more/chasing goals and being stagnant/complacent. Hmm.. another post might be brewing 🙂ReplyCancel

  • omg, love these leaf photos!ReplyCancel

    • Caroline

      Thanks! They were taken right outside my office, this is my favorite time of year in New England 🙂ReplyCancel

  • I think the first step is recognizing what your struggling with and figuring out what is in your control and what is not in your control. I am not trying to build up a business or anything but I take on A LOT of side freelance work just to bring in extra money. I have been telling myself for years that when xyz happens I will stop taking on so much freelance stuff, but in the end I just can’t say no to the extra income so I keep saying yes and then have weeks where I’m driving myself crazy trying to fit it all in! But I just can’t justify turning down the extra moolah either!!ReplyCancel

  • […] think the struggle has been getting the best of me lately, so I decided early Monday morning to commute from my […]ReplyCancel

  • Oh girl, I hear you on all of this.

    Disconnecting and actually taking time to think are two things I struggle with hardcore, as well.

    PS- Thanks for sharing your thoughts and joining in here! Doesn’t it feel good to lay it all out there?ReplyCancel

  • I hear ya on so many of these – especially knowing what to do next!

    I also struggle with being unable to bounce ideas about any of this stuff off anyone else. I mean, my husband listens, and is invested in what I do – but I have no colleagues or work partner to ask: “Am I making sense? Does this sound reasonable or stupid? Am I dreaming big enough? Or too big…?” I feel like I need a soloprenuer support group sometimes!ReplyCancel

  • Thanks so much for sharing this post, Caroline! I can totally relate to many of the items here…especially learning to say and trying to figure out what’s next. There’s no roadmap, and while that’s a beautiful thing, it’s also a little bit scary!ReplyCancel

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