Entrepreneurship: Is Being Your Own Boss Right for You? #Semrushchat Recap

Maria Kalyadina

Jan 08, 201820 min read
Is Being Your Own Boss Right for You

More and more people are saying goodbye to the 9-5 day job… or at least, they would really like to. Entrepreneurship is becoming increasingly popular, and while there are certainly a lot of benefits that come with being your own boss, there can be some additional drawbacks, too.

Entrepreneurship has a lot of moving parts, and while some find it fulfilling, it isn’t the right choice for everyone. In last week’s #SEMrushchat, John Doherty joined us to discuss the advantages and disadvantages of self-employment. This is an area Doherty has a great deal of experience in, being the founder of both Credo and Single Geared, working as an entrepreneur in both B2B and B2C industries.

Check out what both John Doherty and other industry experts had to say when they discussed their experiences with entrepreneurship, and see if being your own boss is the right choice for you.

Q1. Are you an employee or self-employed? What is the biggest benefit of your current position?

There are definitely benefits to being self-employed, but sometimes you lose benefits of traditional employment in exchange. When you are considering entrepreneurship, it is important to look at the biggest benefits of both traditional employment and self-employment, so we asked our chat participants about the benefits of their current positions.

First, we will take a look at benefits of traditional employment, which includes a steady paycheck, job security, and (for many) benefits like insurance or employee-match 401Ks, and retirement plans. This kind of security-- which is enormous-- is something that many know that they waive when they jump ship to tackle self-employment, but what about the other small benefits?

Chat participants frequently mentioned being able to try new or innovative things without the risk. Whether this was due to employer-paid training or more leeway to take chances without it affecting them directly, traditionally employed chat participants noted that trying new things was a huge benefit. Others mentioned that since things like big-picture factors and resources (and, stability) were provided by their employer, they could focus on the parts of the job they loved. And, of course, you can’t forget the camaraderie and support that comes with working on a great team.

So, what about the benefits of self-employment? The two biggest benefits are flexibility and control. Our entrepreneur chat participants mentioned benefits like the ability to work anywhere, or anytime. They would work from home in their yoga pants (dog at their feet) or work while traveling the world. The flexibility of being their own boss also allowed them to create the work that they wanted to be working on and to choose their own clients once they had reached a certain point in their careers. Some also mentioned the freedom to try new things and make mistakes, without being more restricted by a large corporation.

The flexibility also came into play when self-employed workers were tackling projects with clients. They weren’t limited to iron-clad processes or checklists like they may have been at agencies or corporations before; they had more control over the situation and could tailor their solution to best fit the client. You can do what you want, how you want, though of course you still have to answer to the clients paying you.

Self-employment is the ultimate high-risk, high-reward scenario. You give up certain guaranteed benefits like health insurance and a biweekly paycheck, but you get to be your own boss, and-- should things go well-- you could ultimately make much more than you could in traditional employment any day. That being said, as John Doherty mentions in his tweets, it is not right for everyone, but it will be pretty great for the people it is a good fit for.


Q2. What are some benefits of running your own company, versus working for someone else? What are the disadvantages?

As with all types of entrepreneurship (and everything in life, really), there are both major benefits and drawbacks of running your own company.

“Freedom” was the one word our chat participants used more than any other when answering this question regarding the benefits of running your own company. They discussed the freedom to travel or not be tied to one place (or traditional office hours), especially those who did remote work like web development or consulting that could be done anywhere in the world. They mentioned the freedom to run your business exactly how you would like, without the red tape of corporations setting ridiculous rules that made no sense. It also provides the freedom to choose your schedule and to work at your own pace and set your standard.

You also have the freedom to determine your profit. This can definitely be a disadvantage as well, as one participant pointed out, but you aren’t limited to a set agreed-upon income; you can work a few extra hours, or choose only high-paying projects, and increase your income significantly even in one month.

It is important to note, though, that while that freedom sounds incredible, there are major drawbacks to consider, too. While “freedom” is the buzzword for the advantages, “responsibility” was the most commonly used word for the disadvantages.

The responsibility for everything falls back on you. You need to be choosing the right priorities, getting clients, paying bills, and tracking money. It is up to you to either know how to handle everything-- including complex matters like business taxes or law-- or to hire the right people to help you. You can get help, but only if you are paying others to do it, and at the end of the day, no one will care about your business as much as you. This can be isolating, especially if you are working online.


While the freedom to continue to increase your income is a great advantage, the downside is that you have to work a whole lot more to do this. This means that you may find yourself always “on,” bringing work home and finding it difficult to take vacations, or even weekends or a day off. This is especially true during the first few years when you are building a brand and establishing yourself in your field. If you take a sick day, after all, that is fine-- but your business stops for a day, and there is no such thing as sick pay. You can always make more money, but you can’t make more time, and this can be your biggest limitation.

Q3. What are the best ways to balance your current day job with your side business?

Some people choose to manage their business while still maintaining a day job for the security, giving them time to grow their business steadily while mitigating the risk. This is great for those who have the opportunity to do so, but it can be exceptionally difficult to balance.

While it is definitely possible, you want to be careful while doing this. It can be exceptionally difficult, and it is so important to remember that. You risk burning yourself out and under-performing in both positions, sending you backward instead of pushing you forward. If possible, find someone that you trust to delegate tasks to. This may be an assistant or someone who you take on as a partner or an apprentice to train.

Setting boundaries will help you make the most out of the time you have without resulting in you completely overworking yourself. To do this, block time off to work on your business and your day job. Have set hours for both, and don’t let them overlap. You will work more hours overall than if you try to handle both jobs in the same time slots, but you will be endlessly more productive in both positions as a result.

Monitoring progress for your side business is also important. Set milestones and goals that you want to hit monthly, quarterly, and annually. These can include profit goals like revenue, marketing goals like email subscribers, or sales goals. This can help you determine how effective your work is, and if you need to put in more hours, shift your priorities, or work differently.

One chat participant said that he recommended taking tasks with a clear beginning and ending instead of trying to tackle on-going work when you are functioning as a side business. This lets you take on new challenges and build up a client-base, and you can monitor growth and diversify your time. It is also easier to manage your time properly. On a similar note, you can also choose clients and projects that you are most interested in working with to keep your enthusiasm up, making it easier to work the longer hours.

You do need to give it your all if you want your side business to grow into something more, or even if you just want to maintain it. But that being said, you are still employed at your day job, and they deserve your commitment, too.


Q4. What is the scariest thing about becoming self-employed that holds most people back?

Self-employment comes with a lot of potential risks. There is no point in denying that, but some of the best parts of life come with tremendous risk. So, what is the scariest thing that holds people back, and how can they overcome it?

Surprisingly, being afraid of the unknown was one of the most commonly discussed fears amongst our chat participants. What will I do? How will I make it work? How will I even get started? How will I be different from competitors? What challenges will I face? Will I actually be able to make money? What if it doesn’t work? What if this means change? The fear of the unknown coupled with the fear of failure was a powerful one, especially since your own income and financial security can be at risk.

Self-doubt (which can take the form of imposter syndrome) was also a powerful hindrance, with many people worrying about not knowing what they didn’t know. They felt they didn’t know enough to get started, and they weren’t sure where to look. There is so much involved with running a business-- including deciding how much to charge, how to prepare taxes, and how to mitigate those lost benefits-- that it can feel like there is just too much to know, and that they are frauds because they don’t know it yet.

If you ever feel like this, remember that everyone with a six or seven figure business felt like this at some point, and they were able to figure it out- you can, too. Set aside a few hours a week to get started, even if you don’t feel like you are ready. Once you get started, you will feel the motivation to keep pushing forward until you have something very real, even in the face of people who feel the need to doubt you and tell you it is not possible.

Don’t worry about scaling from the beginning, and worrying about having people’s livelihoods in your hand. Instead, focus on the potential of what you dream of building, and find ways to do just that. Instead of thinking “I’ll do it tomorrow,” commit to starting right now, or the decision to do so may never actually come since it is hard for us to ever feel truly ready.


Q5. What tips would you give to a failed entrepreneur to guarantee success?

Sometimes, even the most successful entrepreneurs don’t go skyrocketing to six or seven figures on their first go, and instead, end up stumbling and losing a business. One failure doesn’t mean that you are automatically out of the race, though, unless you let it.

Need another reminder? Consider these successful entrepreneurs who had to fail several times before they succeeded:

  • JK Rowling, who was broke and depressed, was rejected by multiple publishers before one said yes to publishing Harry Potter

  • Walt Disney was fired from Kansas City Star because his boss thought that he lacked creativity

  • Oprah Winfrey was fired from her first TV position as a news anchor

  • Henry Ford had multiple failed businesses that left him broke five different times before he started Ford Motor Company

Moral of the story here: failure isn’t permanent, and as one of our chat participants said, it is only a failure if you make it one instead of learning from it. All failures give us the chance to learn something new, allowing us to grow and do better next time. Trial and error is a part of growing a business, and sometimes you really need to learn from the errors to avoid them the next time around.

That being said, maybe don’t rush right back the thick of things after one failed business. Take some time away to decompress and then, with a more level gaze, take a look at why your business failed. Hold yourself accountable, and know how you’d do it differently the next time.

During this process, surround yourself with great people. Hire a great team of support staff if you need it, or find mentors, or join a networking group with other entrepreneurs who genuinely want to see you succeed. They will be able to provide unparalleled support and advice to help you grow and overcome the obstacles you struggled with before.

Moving forward, remember to set SMART goals. These goals are specific, measurable, achievable, relevant, and time-bound. Take your past mistakes into consideration when setting them, and use these goals to evaluate your progress moving forward. And remember, everyone fails at some point. We all fall down because nothing in life is guaranteed. Treat it as a learning experience, and pick yourself back up. Failure is not the end of the world if unless you let it be.


That's all for today! Make sure you join us this week on #SEMrushchat with  Alexander Kesler as we discuss "Combining SEO and CRO to drive engagement!"

Author Photo
Maria is the Social Media Marketing Manager at Semrush and the host of the weekly #Semrushchat. You can always connect with her on Facebook and follow her on Twitter! Join the #SemrushChat every Wednesday at 11 am ET/ 4 pm BST!