Two Years Self-Employed: Lessons From Becoming Your Own Boss

Being Your Own Boss - Becoming Self-EmployedMy official last day at my traditional job was October 11, 2013.

It’s hard to believe it’s already been two years since I sat at that old desk.

Becoming self-employed has been one of the best decisions I’ve ever made. If you’re considering it, I highly recommend exploring the path of being your own boss.

I’ve built a business I believe is successful, I’m having the time of my life, I control my future, and I can travel whenever and wherever I want. Those freedoms are invaluable.

If that doesn’t sound great, I’m not sure what would.

For context, I used to work as an analyst at an investment banking and valuation firm. I followed the typical 8-to-5, Monday through Friday routine and realized I didn’t see a fulfilling future there. My role was stressful, packed with deadlines, and full of responsibilities that didn’t excite me.

If you’re new here, these posts may help you learn more about my journey and how to pursue self-employment:

  • My Monthly Online Income Reports
  • Why I’m Happy I Left My High-Paying, Secure Job to Blog
  • How To Prepare for Self-Employment
  • How To Make Money Blogging
  • How To Live Life To The Fullest

As I mention in my monthly reports: life is great now. I love everything about self-employment and blogging. I’m still extremely glad I took the leap and can’t imagine going back to that old routine.

Call me spoiled or call me content—I don’t mind. Life is good, and I believe many others can follow a similar path. I know several readers who have made comparable transitions, and their stories are encouraging.

Below is an update on how things have evolved for me two years into self-employment.

I enjoy being in control and being my own boss.

One of the biggest advantages of self-employment is autonomy. I love deciding how to spend my days, creating my own schedule, setting goals for the business, and managing the behind-the-scenes work. That level of control has significantly improved my work-life balance.

I’ve adopted a personal rule: I don’t do things I don’t want to do. That doesn’t mean I refuse every opportunity—far from it—but I avoid tasks that drain me or conflict with my values. That boundary helps me stay motivated and focused on what matters.

Related suggestion: If you’re thinking about leaving your job, research negotiation strategies and options for transitioning out of employment in a way that suits your circumstances.

I love my business.

I genuinely enjoy every service I provide and each aspect of the work I do. From writing and content creation to promotion, networking, and engaging with readers, I find real satisfaction in these activities.

Running an online business isn’t for everyone, and it can be misunderstood by some, but it suits me. If you’re curious about starting a blog, there are affordable ways to begin and grow one gradually while learning the skills needed to succeed.

Working from home is a major perk.

Eliminating a commute has given me more time and flexibility. Because I enjoy my work, getting up in the morning is no longer a chore. I look forward to starting my day and often find it hard to step away from my laptop.

Endless access to the fridge—manageable with discipline.

I’ve put on a little weight since becoming self-employed, but it’s not as bad as I feared and I’m addressing it. Of course, there are days when I snack more than I should—we’re human—but most days I’m able to maintain a healthy routine.

Flexibility is priceless.

One of the greatest benefits of being self-employed is a flexible schedule. I can work ahead, choose when I work, and break my day into productive chunks. Some days I work in the morning, hike or meet friends midday, and return to work in the evening. I can schedule appointments without stress and work whenever I’m most productive—morning, night, or weekends.

Location independence lets me work from anywhere.

Being location independent has been liberating. My online business allows me to work from wherever I have an internet connection and my laptop. In fact, I’m writing this while in my RV and enjoying the scenery.

The tradeoff is that separating work from life can be challenging. With work always accessible, taking a truly disconnected vacation requires discipline. Still, I’m grateful for the strong work-life balance I’ve been able to create.

Related idea: If you’re drawn to travel and remote work, consider ways to structure your schedule so you can enjoy destinations without compromising productivity.

My social life has improved.

A common concern about quitting a traditional job is losing social interaction. For me, the opposite happened. At my old job I was one of the only women and most colleagues were decades older, which limited social connection. I often spent entire days without meaningful conversation.

Now I interact with people throughout the day. My partner, Wes, works alongside me, I meet people through outdoor activities, and I regularly connect with friends and fellow bloggers. My social life is richer and more varied than it was before.

Questions: Do you have questions about self-employment? Are you thinking about becoming your own boss? Why or why not?