How I Realized I Couldn’t Keep Working for Someone Else

As many of you know, I left my day job last year and now work for myself from home.

I quit in September 2013 and my last day was in October. I have never once regretted the decision to leave.

Below are the reasons I knew I could no longer work for someone else. My day job paid the bills, but it wasn’t enjoyable. Just as freelancing isn’t for everyone, that job wasn’t right for me.

I dreaded Sundays and Mondays.

Sundays were awful because I knew the workweek was about to start. Mondays were even worse: the work was boring and stressful, and I felt overwhelmed. Working independently at the company left me with almost no colleagues to talk to, and the clients I did meet were mostly older businessmen. The job offered little social interaction and did not suit me.

Since I switched to full-time freelancing, I actually look forward to every day. I enjoy pursuing new leads and serving my current clients. Even though I work from home, my social life improved: I connect with other freelancers, friends, and family throughout the day.

 

My vacations were okay, but I knew they could be better and longer.

At my day job I received a fair amount of vacation time—around three weeks per year—but being on vacation didn’t always mean I could disconnect. Work piled up while I was away, so I often had to work extra hours to catch up. The days before a vacation were stressful too, as I rushed to complete everything before leaving.

I was on track to become a vice president, which would have meant greater responsibilities and being on call almost constantly. The idea of being on call 24/7 for a job I found boring and stressful was discouraging. The vacation time I had also covered sicknesses and emergencies, so it didn’t always feel like true time off.

 

My side income became higher than my day job income.

When my side income exceeded my salary, staying motivated at the day job became difficult. I realized that if my freelance income kept growing, it no longer made sense to sacrifice my happiness for a role and industry I didn’t enjoy.

 

I saw others around me hating their jobs.

After landing my first professional job out of college, I began to notice how many people genuinely disliked their work. Their unhappiness influenced everything they did and limited their freedom. I didn’t want that for myself. I saw the potential in my side projects and decided to pursue them, hoping I could create a better path than the one I had been on.

 

I wasn’t in control.

At my day job I rarely felt in control, despite being a strong performer. I often felt like I was walking on eggshells, unsure of what the future would bring. Even if my position seemed secure, uncertainty weighed on me.

Now that I’m my own boss, I feel much more in control. I choose my projects, set my schedule, and design the way I want to grow my business. That flexibility and autonomy make a huge difference.

 

I couldn’t keep wasting their time or mine.

My heart wasn’t in the work I did. The fit was wrong, and I came to realize I was doing both the company and myself a disservice by staying. I didn’t see myself staying long-term, and it felt unfair to remain in a job I wasn’t invested in.

 

Do you ever want to work for yourself? Why or why not?

 

P.S. I drew inspiration for this post from Holly. Last month, Holly at Club Thrifty published an article titled “Why I Would Rather Be Poor Than Work for Someone Else.” Her post motivated me to write this follow-up and reflect on my own experience.