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What I Learned In My First Year Of Self-Employment

Do you dream of being your own boss? Here are the top tips and lessons I learned during my first year of self-employment!

When I started The Blissful Mind in 2014, I had no idea that it would become such a huge part of my life. Blogging was just a hobby that gave me a creative outlet to share my ideas with the internet.

I couldn’t have predicted that blogging about wellness would inspire me to attend graduate school for wellness coaching, or that blogging would allow me to do three things I love: write, create, and help people.

Do you dream of being your own boss? Here are the top tips and lessons I learned during my first year of self-employment!

But in 2017, I was faced with the decision to either find a new job or choose the self-employment route. Even though it was terrifying, I took the leap. A year ago, I chose to create a business out of The Blissful Mind, and somehow I’m still going.

Through coaching, blogging, and creating eProducts, I’ve been able to make this self-employment thing work. I’ve also taken on part-time jobs and hustled my way through the tough times.

So many people dream of being self-employed, and sometimes I forget what a blessing it is to be in this situation. It’s hard work, I tell you. It makes you question everything you ever knew about yourself, your abilities, and your sanity. But it also gives you so much in return.

“One of the huge mistakes people make is that they try to force an interest on themselves. You don’t choose your passions; your passions choose you.” – Jeff Bezos

I want to share what I’ve learned over the past year in case you’re thinking about taking the leap too. There are so many things I could share, but I’ve whittled it down a list of the top 12 lessons I’ve learned during my first year of self-employment. Keep reading to find out what they are!

12 Lessons Learned From Being Self-Employed

Do you dream of being your own boss? Here are the top tips and lessons I learned during my first year of self-employment!

1. Every day feels like a rollercoaster.

Some days you’ll feel so motivated because everything is going smoothly. Other days, every little thing will go wrong, and you’ll wonder if you should apply for a 9-5 job again. Know that this is completely normal and all entrepreneurs go through these ups and downs. It happens with any job, really.

If you feel like you’re in a rut or question whether you should keep going or not, remember to give yourself space and take a break.

2. You have to ask for help.

I struggle with asking for help because I’m a perfectionist. I’m sure you can relate. The thing is that you can’t do everything in your business. You might have a lot of talents, but there will only be a few things that you’re really good at. Take the risk and hire an assistant to do the things you aren’t amazing at or hire a coach to help you through your struggles. That way, you can spend more time doing things from your zone of genius.

3. Planning quarterly is a game-changer.

I had no idea how the first year of being self-employed would look. Though I had lots of ideas, I didn’t have a concrete plan. I tried to do everything at once and failed miserably.

I attempted to plan out a whole year ahead of time, but I realized I couldn’t stick to something that far in advance. What eventually worked for me was planning things quarter-by-quarter. I focused on 3-4 top goals or projects to complete during that time, and my workload became more manageable. You’d be surprised what you can get done in a solid three months.

Do you dream of being your own boss? Here are the top tips and lessons I learned during my first year of self-employment!

4. Self-discipline is vital.

A lot of people dream of being self-employed because they want the freedom to do things on their own terms. That was one of the most exciting things to me. Like, you can go to the mall in the middle of the day on Tuesday because you create your own schedule?

Yes, you can do that and the freedom is GLORIOUS. But you’ll start to realize that if you don’t practice self-discipline, you won’t get your work done. There’s no one to tell you what to do anymore (which is amazing, obviously), but you have to act like a boss and follow through with your plans.

Related: A Simple Way To Plan Your Day For Success

5. Taxes aren’t that scary.

One of my biggest fears going into self-employment was the fact that I’d have to do my own taxes. I’m still not 100% sure if I’m doing everything correctly with my business income, but I do know that filing my own taxes went a lot smoother than I expected. I used TurboTax Home & Business, and it guided me through the whole process. That being said, one of my next goals is to hire an accountant to help me stay on top of everything money-related.

6. People won’t understand what you do.

I’m grateful that my family and friends support my choice to be self-employed. I’m not sure they totally understand what I do, but then again, do we know what any of our friends really do in their jobs?

Despite this support, there are still those people who ask me when I’m going back to a real job. It feels like a kick to the stomach, but most often it just comes down to lack of understanding. You have the choice to help them understand what you do, or you can brush their comments aside and keep moving forward.

Do you dream of being your own boss? Here are the top tips and lessons I learned during my first year of self-employment!

7. Connect with others because it gets lonely.

I’m an introvert by nature which makes self-employment perfect for me. However, it can get lonely when you spend 99% of your time by yourself. Social media is great, but it doesn’t give you the same feeling as being in someone’s presence. One of the things I haven’t been great at is keeping up with friends because I’ve been so focused on my business. I’m lucky that I’ve made some great self-employed friends through social media, but I also know that in-person connections are the greatest of all.

8. There’s no shame in getting a part-time job.

Self-employment means your monthly income will often vary. Some months I made $3k and others I made $400. Because I wasn’t a fan of having anxiety around money every month, I found a part-time job that would give me a predictable paycheck.

At first, I felt guilty about getting another job because it meant my business wasn’t sustainable. But in the long run, it gave me peace of mind and took some of the pressure off of my own work.

9. Staying organized is key.

I’m a pretty organized person, but running a business takes another level of organization skills. There are so many things to keep track of, which is why it’s so important to have the right tools for the job. Here are some of the tools that have kept me and my business organized:

  • QuickBooks for bookkeeping (keep on top of this, it’s important)
  • Dubsado for client onboarding and payment processing
  • Acuity Scheduling for scheduling meetings and calls (saves back and forth emails trying to find a time that works for people)
  • Asana and/or Trello for planning out projects and breaking goals into manageable steps
  • Todoist for staying on top of daily to-dos
  • Google Calendar for staying on top of appointments

10. You have to be strategic.

When you first start out, you’ll realize there are so many things you can do now that you have the time to pursue them. I actually felt overwhelmed by the amount of time I had to work on my business at first. I no longer had just the evenings and weekends to work on it, so I crammed my day full of tasks.

If I could re-do those first few months of self-employment, I would write a list of all the ideas I had for my business, then rank the list by the ideas that a) would make me money b) I would enjoy doing and c) would be relatively easy. If you can find an idea that combines all three components, go with that one first.

11. Self-care fuels your work.

There’s so much to do in your business, so it’s easy to forget to stop working. You might even feel guilty about not working because there’s always something that could be done next. It’s amazing to not hate your job and want to work on it all the time, but self-care is a vital component to your best work. It might feel like you’ll lose money or your business will crumble if you prioritize self-care overwork. More often than not, the opposite will happen because you’ll approach work from a well-rested and calm state of being.

Related: 5 Self-Care Tips For Entrepreneurs & Bloggers

12. You are not your business.

When you’re working on your business all day, every day, it’s easy to forget that there are other things in life to enjoy as well. It’s a blessing to enjoy your work, but you have to detach in order to make progress. Make time to explore other hobbies. Meet up with friends. Take time away from your business social media accounts. Give yourself regular chunks of time to completely switch off from your business.

Would you ever take the leap into self-employment?

I hope this post has given you some insight into what it’s like to be self-employed. It’s not an easy path to take, but it’s been the most rewarding thing I’ve ever done in my life.

About the Author
Picture of Catherine Beard
Hi, I'm Catherine! As the creator of The Blissful Mind, I love exploring ways to make life more fulfilling, especially when it comes to our daily routines, habits, and well-being.

22 Responses

  1. I couldn’t agree more with everything you said. When I first started my own business, I was trying to do everything myself… and a lot of those weren’t even that important. Once you get clear on what your priorities are, everything changes.

    And I so hate it when people ask me what I do. They just never get it lol.

  2. Thank you Catherine for your advice this week, I always learn something new from you. I’m going to try your quarterly priority strategy :)

  3. It’s really interesting and true what you wrote! I can relate with you so much here, since I’m hoping to leave my office job by the end of summer and start supporting myself only from managing bussiness’ social media channels. I have a question for you. You said that you feel lonely sometimes; haven’t you thought of renting a desk in coworking space? I work in that way right now, and I think I will continue when I leave this company. Wish you all the best! :)

    1. Hi Maria! I’m excited to hear that you’re planning to be self-employed too! I’ve definitely thought about it, but I’ve never been able to find a place that I felt was reasonably priced, especially here in Seattle. I have found that something as simple as working from a coffee shop can help though. Just being in an environment with other people around you, even if you’re not talking to them, can feel less lonely.

  4. An encouraging read! The takeaway point for me were the ‘staying organised’ and the quarterly planning – both of which are a bit of a learning curve!

  5. I’m at that crossroad in my life where I am willing to take a leap into self-employment but also scared to death to do so. Your article was very inspiring and I will definitely be referring back to your blog in the future. :)

  6. Thank you Catherine for sharing your own experience in entrepreneurship.. I’ve enjoyed reading that and really picked up some inspiring thoughts

  7. Just about everything you outlined is me right now. I always knew I wanted to be self-employed, but fear of the unknown took precedence over everything. As the years have passed along, my desire, the urge and the sheer “it’s a must” has grown. I, by some divine intervention, was forced to move outside of corporate America, and from there I knew/know I never want to return. Knowing this, I have completely taken my leap of faith into this self-employment thing and it has been VERY slow to take off and discouraging some days; but to give up now would be me saying that I’m okay with taking 10 steps back. I have so many ideas in my head, but just don’t know where to start or if it will work. I will remain faithful and intentional though. Blogs like this remind me that I am human and I am only one of many who is going through this transition and experiencing these feelings. .

    1. I know exactly what you mean! There are days when it’s super discouraging and nothing feels like it will work out, but the next day is completely fine. Thank you for sharing your experience too – it makes me feel less alone as well :)

  8. It is evident that you’ve got talent, Catherine! This was a great post, and makes me excited for self-employment. I’m hoping to take the leap in Spring of 2019, but I also love working a “normal” job where I can be around co-workers!

    Keep up the amazing work!


  9. I feel every single point every day. It makes me feeling not that lonely. Thanks a lot for the article.

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