The 10 Most Important Lessons I Learned When I Decided to Work for Myself


woman working from home


Hilary Thompson
Hilary Thompson14
April 24, 2024 at 6:17PM UTC
After spending ten years in the corporate world, I finally decided to make the leap and work for myself. Over the past five years, I’ve created a successful business and could not be happier. As I’ve reflected upon my time as a self-employed writer, I’ve realized what it’s taken to get me here. Below I list the ten most important lessons I've learned since becoming my own boss.
1. Life insurance is a must.
When I left my employer, I left behind all my benefits, including fantastic life insurance. Over the course of the first few months, I didn’t consider life insurance to be a necessity. However, I soon realized that I needed the peace of mind of knowing my husband and children would be financially taken care of, if something happened to me. I went out and purchased a policy the next day. There are many advantages and disadvantages to life insurance, but as a breadwinner, I decided that I needed that comfort to take care of my family—should the unexpected happen
2. Don’t forget health insurance.
Not only did I put off buying life insurance, but I also put off enrolling in a health care plan. I didn’t realize how much I’d miss a group health plan. When looking at different health care plans, I found some providers were better than others. Take a look at the best insurance providers for the self-employed.
3. Roll your 401(K) into an IRA.
One of the things I worried about when leaving my employer was my 401(K) account. I was scared of losing everything I had saved for retirement, once I quit. Luckily, the benefits of rolling my 401(K) into an IRA account allowed me to keep investing for retirement. Not only could I keep saving, but I also had more options. An IRA account gave me more investment options and flexibility.
4. Managing your time is crucial.
Being your own boss is great. Setting my hours and being able to take time off whenever I needed was exactly why I decided to go rogue, in the first place. However, when I first started working for myself, I struggled managing my time. I concluded that if I wanted to be successful at home, I needed to make some changes. Cutting out social media, using online time management tools, and setting up an actual work schedule helped me stay on top of my work and make better use of my time. 
5. Eliminate distractions from your workspace.
Working from home can get distracting. There were times that I would do a load of laundry instead of answering an email—maybe take an hour to declutter my daughter’s closet. Recognizing that I was getting distracted by things around my house led me to remove myself from any distractions during working hours. Instead of working at my kitchen table, I started working in my husband’s study. I would shut the door after dropping my kids off at school and just work. Eliminating those distractions helped me focus and made me more successful.
6. Learn how to delegate.
Before I started working for myself, I had an employer who delegated tasks. Suddenly, assigning tasks was my responsibility, but I was unsure and unwilling to distribute work. I wanted to take steps to efficiently delegate, so I started small. Asking a financial firm to handle my taxes and freelancing a few blog articles out every month helped me focus on more important tasks.
7. You can’t avoid taxes.
The only thing I miss about being employed is not having to worry about taxes. Becoming self-employed meant that was now my responsibility. I discovered plenty of ways to manage my taxes after becoming my own boss. I set aside money each week to cover my tax fees. I also save every receipt and am diligent with my bookkeeping. Now, when tax season comes around, I’m a lot better prepared and less stressed.
8. Balance work and life.
Balancing my work life and my personal life became significantly harder when I first became self-employed. I was busy and paranoid I wasn’t doing enough to ensure the success of my business. That led to the neglect of my family, my home, and my hobbies. Finding balance meant becoming more strict—not with working, but being mindful of my family’s needs. At night, my laptop remained in my office, and my phone was turned off. I set aside a few hours every night to spend with my family. Those few changes led to a more balanced, happy work and home life.
9. Be a good boss.
Sometimes I forgot that I was my own boss, which meant there were times I didn’t treat myself like I should. My first few business trips were spent in cramped motel rooms; eating crappy, fast food; and taking the cheap flights in the early hours of the morning. No good boss would expect their employees to do that, so why was I doing it? I learned to treat myself like I expected a good boss to, and it made all the difference. I was happier and more productive, which lead to more success.
10. You reap what you sow.
Perhaps the most significant lesson I’ve learned while working for myself is that success depends on me. If I slack off or waste time, it is my own pocket I'm stealing money from. Additionally, I learned that I’m only accountable to myself. Reaching my full potential and and ensuring the success of my business is entirely up to me.
These ten lessons I’ve learned have been well-earned. It was a little rough at first, but I've slowly learned how to manage my time, be efficient, and take care of the leg work necessary while still enjoying the perks of being self-employed.

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