11 Things You Need to Know About Being Your Own Boss


It Isn’t All Trendy Cafes and Almond Milk Lattes …

The idea of being an entrepreneur, freelancer, or “being your own boss” can be so alluring at times. Waking up whenever you want, working in your pajamas in front of the TV at home or from all of your favorite coffee shops around the city while sipping on the finest almond milk lattes and loose-leaf teas, nobody telling you what to do … who wouldn’t want in on that lifestyle? The world is your oyster, right? Well … sorta.

There are a lot of common misconceptions about the “entrepreneurial”, “freelancer”, or “blogger” lifestyle, and as a self-employed freelancer, new entrepreneur, and “influencer” (this word still makes me cringe a little), I’m here to debunk the falsehoods, reaffirm the truths, and tell you everything you need to know that I’ve learned so far in my short time doing this. Trust me, I’m still learning myself.

  1. You can do it.

    The most incessant fallacy of the entrepreneurial lifestyle is that it’s unattainable. To the majority of us, it’s a long shot, a far-fetched dream – most often believed to be for the exclusive few who either got lucky, came from money, were the popular kids in school, or (oppositely) the recluse programmer or engineer with no social life growing up because they were building a product or the next big app to change the world. But the truth is, the only “exclusive” group you have to be a part of to be in this industry, is the group of the very few who truly want it bad enough. Contrary to popular belief, that group is open to the public. The caveat, though, is recognizing and actually applying the amount of work it takes to be a member of that group. Not many are truly willing to put in that level of work, and that is the only variable standing between you and a free, lifelong membership to the “be your own boss” club.

  2. It won’t happen overnight. It probably won’t even happen in a year (but it could). 

    Be prepared to lose sleep. Patience is truly the best practice here. Ever heard the saying “It takes 10 years to become an overnight sensation?” Nothing could be more accurate. I’ve always, always said that if it’s not a 9 to 5, it’s a 24/7. Thanks to social media platforms and the wonders of the world wide web, we can gain visibility quickly these days. But the people and brands who gain visibility quickly and actually retain people’s attention, have likely been working tirelessly for years up until that point to make it so they’ve built something worth following. In this day of instant gratification, so many people quickly get discouraged when their work isn’t recognized immediately, but these things truly take time. Make the time to hone in on your craft, to harness your skill, and to develop your unique vision so you have something different to bring to the table in this incredibly inundated age of overstimulation.

  3. In terms of creating your own blog or media platform, unique content is key, but consistency is paramount.

    While unique content is important, often times what will really set you apart from the rest isn’t simply your content, but your consistency. What good is great content if it’s posted once a month and dies off in between? The truth is, people will forget about you rather quickly, no matter how unique your content is, so consistency is the only way to stay relevant. Your beautifully written piece or your wonderfully composed set of photos will fade to the background if there’s another blog in the blogosphere giving your potential readers something to come back to daily.

  4. Nobody can tell you what to do … except yourself.

    Sure, not having anyone else to answer to can be great, but the catch is now you have YOU to answer to — and if you’re anything like me, that can be far more demanding than answering to anyone else. We are our own worst critics, so it’s highly likely that you’ll be harder on yourself than anyone else would be, and it’s only you that is held accountable. This calls for extreme discipline. This means that if you fail or make a mistake, you only have yourself to blame. That can be an incredibly heavy burden to carry, so make sure you turn every failure or mistake into an opportunity for learning and growth. Then on the contrary, when you accomplish a goal or hit a milestone, that is yours to own and no one can take that from you. That said, don’t be afraid to celebrate even your small victories with a glass of wine or a shot of tequila. 😉

  5. Manage your time and manage expectations (including your own).

    Being your own boss can often lead to spreading yourself too thin. Whether it be that you’re overly eager to take on projects because you don’t want to miss opportunities, or maybe you’ve just never had to manage your own time to such an intense degree, over-committing happens more often than not, especially when you’re first starting out. The answer? Manage everyone’s expectations, including your own. Overpromising and underdelivering ends in a loss for everyone, so avoid that at all costs. Make sure that your clients and partners respect your time, and equally important, make sure you respect your own. Dreaming big is a must, but when it comes to productivity and the day-to-day tasks, setting realistic goals and creating actionable plans are essential. If someone asks for too much in too little time, don’t be afraid to express why it can’t happen, but also always make sure you also provide a solution. Providing solutions creates a peaceful and proactive compromise to an issue that could otherwise be left open-ended or unresolved by simply saying “no”.

  6. Be prepared to invest in yourself (whether it be time or money) wherever necessary, and be patient on the return.

    Being a shooter, I’ve always said that one of the main things I never mind spending money on is my camera equipment, because I consider it an investment in myself and my craft. I’m providing myself with the tools I need to succeed. I know that if I spend money on camera equipment or software that streamlines my workflow, I easily make that money back through the work I do and the time saved. Blogging can function in the same way, but it’s a much slower process (freelancing can also be a slow process in the beginning). Want to be a photographer? Start with your camera phone and work your way up to a DSLR. Take some online courses because we live in an age where you have endless information at your fingertips. Want to be a travel blogger? Take a few trips (no matter how small) on your own dime and build up the content. Write about your experiences and give people a reason to pay attention what you have to say. Once people really begin engaging with your content, you’ll start getting the attention of prospective brands and clients.

  7. You have to create your own opportunities, especially when starting out.

    Never underestimate the power of the ask. Don’t be afraid of cold-calling (or cold-emailing) and don’t be afraid to pitch ideas or bid to clients or brands. Once you begin establishing yourself, there are a lot of brands that are willing to work with you or support your platform, if you do most of the thinking for them. See a brand that you want to work with? Figure out what they’re looking for or what they need, and find a way to leverage your skillset and/or your platform to fulfill that need. Also, recognize the difference between being an entrepreneur or freelancer and being a blogger or influencer. Bloggers or influencers are essentially their own brand, so when working with other brands it’s treated as more of a partnership or collaboration rather than a client relationship. If you’re looking to become an “influencer”, when pitching your ideas, make sure you have their brand in mind as well as yours. See to it that it aligns with their brand message and core values, and you can’t go wrong. The worst that any brand or client can do is say “no”, and when that happens you simply learn what you could have done better and move on. Rejection is inevitable, and it’s to be expected. You’ll get used to it.

  8. It can get really lonely.

    The expectation is that every day is a jam sesh with all of your other talented, entrepreneurial friends at the trendiest cafes, restaurants and co-working spaces, where you bounce ideas back and forth and create vision boards while listening to your favorite playlists. The likely reality, though, is that every day you wake up and either you work alone at home or you work at a coffee shop (still alone) and no matter how many friends you call or text to work together at the cafe, no one can meet up because they’re at their day job. You’re a lone wolf, and freelancing is the most intimate of work environments. The upside is that you learn immeasurable amounts about yourself — about your boundaries, your limits, your thresholds, your levels of personal motivation. So embrace the loneliness and the solo intimacy, but know how to balance that with human interaction from time to time. Then if you feel the need, find your wolf-pack of fellow entrepreneurs and freelancers to surround yourself with when you crave a social environment and that extra hit of mental stimulation.

  9. This industry can be competitive, but it thrives upon collaboration.

    This ties back into the idea of this industry being an “exclusive” club. It can be clique-y, and in some areas of the freelancing/entrepreneurial/blogging world, others might seem “catty” in their race to the top. If you’re doing your thing, the likelihood is that you’ve got other people watching you. But that’s always a good thing, so embrace it. If you’re kind and personable, you’ll attract like-minded individuals within the industry and you’ll find that it can actually be a truly supportive and respectful community, built on cross-promotion and cross-pollination. You’ll learn that a lot of creatives or entrepreneurs are really willing to help one another on some level. You might be a lone wolf on a daily basis, but fitting collaborations when the opportunities present themselves are highly encouraged. We are all in this together, after all.

  10. Know your worth.

    Being self-employed means you’ll come across people or brands who might not understand your worth and the value you provide. You’ll often be considered the “small fish” and someone might try to corner you into doing too much work for too little compensation (or no compensation at all, and rather, in exchange for “exposure”). You have to be smart about this. When an opportunity comes your way, take the time to analyze the big picture. There are a ton of different possible scenarios – some with very obvious answers, others that are more debatable – but they all boil down to the same thing: will this make you happy? There will be opportunities that arise that are worth doing for little money because the “exposure” is legitimately a fair (or far greater) return, and there will also be opportunities that arise where the return is remarkably less than the time and effort required to complete the project, making it unworthy of your time. And then sometimes there will be projects where there isn’t a huge return, but you wholeheartedly believe in the work that’s being done, so you want to be involved anyway. These situations are all completely fine, and you’ll have to tackle each on a case-by-case basis. When considering compensation, if the terms don’t feel quite right but it’s something you actually want to pursue, remember the value you bring to the table and don’t be afraid to negotiate terms that better suit your needs.

  11. It’s worth every damn bit of struggle, if you want it bad enough.

    The risk, the possibility of being broke for a little while, the loneliness, the sleepless nights, they’re all a small price to pay for the life of freedom and choice that you’ll be building for yourself should you decide to pursue entrepreneurialism. If you ever end up becoming your own boss, never forget about what a luxury and a blessing that is. No matter how much you might feel lonely or overwhelmed at times, always remember how lucky you are to be living your life on your own terms.

High risk, high reward.

Now, I’m thinking that since you’ve taken the time to read this lengthy post, chances are, you’ve thought about or are currently considering pursuing your passions, freelancing, starting your own company, or starting a blog, but you’re unsure as to whether or not it’s right for you. Hopefully what I’ve written has helped enough to where the only question you have left to ask yourself is … do you want it bad enough?