18 Struggles of Being Your Own Boss that No One Talks About


If you’re your own boss, I don’t need to tell you the struggle is r-e-a-l. Whether you’re an independent consultant, solopreneur, have a team of people working for you, or working a side-hustle, you get it. 

Can we be totally honest? For a moment, let's remove the veil and give a shout out to all our sisters who are working their butts off trying to appear as though they've got everything figured out. I know, I know, it's hard to admit because if we don't appear to always be “killing it”, how the heck are we going to convince people to buy our products, services or join our teams?

But remember, what people think of us is never as important as what we can do for them. When we focus on the value we offer, or as I like to say, "making our honey", we can stop the mind games by taking ourselves out of the equation. 

So just for a minute,  let out a big sigh, stop worrying about how many followers you have, and get real with me. 

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18 Struggles of Being Your Own Boss that No One Talks About

  1. Maintaining Belief — ok, this one is hard for all humans to be honest. But especially hard when people are asking, "So, what is it you do again?” or, “How is your business going?" Even if people aren't playing the critic, you hear the judgement in their tone, like they're questioning whether you're legit or if you should get a "real job"?

  2. Work is Non-Stop — whether your biggest worry is cash flow, ranking up, or

    attracting clients, it's hard to shut your business off. Even when you're in bed and your to-do list is circulating in your mind, you think, "ok, just one more thing...". Then it turns into another, then another. Sometimes there are so many things you could be doing, that the overwhelm actually just gets you stuck in anxiety-mode.

  3. There's Never Enough Cash Coming In — since there are so many things that could improve your business plus make your life easier it makes sense to invest in resources for growth. But it's hard to invest until you see a steady flow. Especially for us women, a lot of us feel guilt in making things easier on ourselves, even when we believe we'll see a return on our investment. Going into debt for our business is scary s#i+.

  4. Letting go of the Notion of ‘Perfection’ — sounds easy enough, right? Some people are proud of being a perfectionist, but what I've realized— perfection is just fear in disguise. It's a way to keep us safe from judgement of others. But it's a luxury us bosses can't afford. If we waited until everything was "perfect" we would never even start. We would be unproductive and wouldn't have a chance to learn.

  5. You Will Have an Identity Crisis at Some Point — "Can I be both a good mom/ wife/ friend/ social advocate and run a business successfully?" In our culture we are more forgiving of men fulfilling multiple roles than women. We know we are being judged more closely, and it's hard to tune the cultural narrative out. But to be successful, you have to merge those identities and redefine those roles yourself. 

  6. Fear of Failing Publicly — this is especially when we start out or try to take our business to the next level. To really be out there with our business, we are announcing to the world that we are doing this. And people will be asking how we're doing. They care, of course. But we also know most businesses fail in their first year, and we don’t want to be reminded that we might be one of those businesses.

  7. Everyone's a Critic — you'll get all sorts of feedback, lots of it conflicting. Some is well intentioned but out of touch and other feedback is valuable but sometimes hard to incorporate overnight. And what makes it worse is, sometimes our worst critics are the ones that love us most. They don't want to see us fail or get hurt, true, but going back to #1, it doesn't help us. And it's exhausting always trying to explain your business, because let's be real- what you're selling won't be for everyone. And that's ok.

  8. It's a Roller Coaster of Emotions — managing the ups and the downs of a business is challenging. Even when your business is stable, as you ride the waves of everything from self-doubt and mental exhaustion all the way to celebration, it's hard to always be the person you need to be to stay on track with your goals. No wonder roughly 50% of the self-employed struggle with anxiety or depression.

  9. It Can Be Socially Isolating — if you have friends that don't fully get it, or if you work from home and don't have a lot of interaction in your day, it can get lonely at times. Bosses learn fast that we need to build a network of supporters in order to survive, and eventually thrive, in our businesses. 

  10. Building Trust in Today's World is Hard — with all the competition and rapidly decreasing attention spans, you need to stand out and make your message compelling. Because, there's all these sales-y, spammy tactics being used to compete, it makes it even tougher to build trust with people. It takes patience and coming out of your shell to be real and connected with your customers. 

  11. You're Always Re-Defining Your Niche — since it's so hard to build trust, it's important you're marketing to the right niche market. There's an art to leveraging your strengths and passions and aligning them to what is most needed in the world. And when the world is changing faster than ever, you need to always be evolving to keep up.

  12. Stress Takes on New Meaning — to be your own boss, you need to care a lot. And when we care a lot, we have to be careful of attaching our own self-worth to the outcomes. Still, it beats the stress of having little control over your life in a job that is less fulfilling. 

  13. Imposter Syndrome, What!? — as women, we experience guilt and shame differently than men. Most of us are told to be nice, put others first, and take the least risky, conventional route. When we have to be an authority in our field, a leader, or salesperson it feels icky or inauthentic

  14. Time Management Needs a Strategy of It’s Own — finding the right balance of working on your business vs in your business is a challenge. When you factor in all the other expectations we put on ourselves, plus all the strategies that could potentially grow our business, time is that much harder to manage. 

  15. One Way or Another, You Have to Face your Fears — again, no wonder most businesses fail in their first year. Not only do you have to maintain the belief and overcome the daily challenges, but you also at some point will have to face a fear to get to the next level. For me, my demon is public speaking and I've had to deliberately put attention and work around that in order to keep growing my business, and inevitably myself. 

  16. Shiny Course Syndrome — there is so much to learn! So naturally, every course that looks like it's selling you gold, you want to seize as an opportunity to learn. But the downside to this is we don't always have time to put the learning into action. Sometimes, when you’re in learning mode, it means you're stalling the real work that needs to happen — whether it's on your business or yourself. 

  17. Comparison Syndrome — yup, another “syndrome”, I know. If we knew we were prone to all this, we would never have started, right? The sooner we learn that comparing ourselves to others is useless, the better. It's easy to compare and become distracted. It's hard to remember we are only seeing part of the real picture of the businesses and people we are comparing to. Also, instead of worrying if we are keeping up with the trends, we forget that we could be spending that time on setting the trends ourselves. 

  18. There’s No Clear Direction for You to Take — yup, this is where the leadership part comes in. You're now the CEO of your career, business, and life. Sounds awesome, but you need to constantly be taking a step back to look at the bigger picture and stay focused on what matters most. Dealing with uncertainty is a skill of its own to master. Why do you think so many people out there are selling you blueprints? Sorry, but there’s no blueprint that will guarantee you success. And if there was, would it bring you fulfillment and centre around your own values and strengths? I’m guessing not…


Those are the struggles from my point of view. Share this post with your boss friends and your loved ones! Let’s start being more honest about the struggles and celebrate how far we’ve come. Even if you’ve just started, you’ve probably experienced a lot of this and will hopefully be more prepared for what’s to come.

Do you see any struggles that you would add? Comment below and let me know so I can update the list.

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