Freelancing: A Challenging Emotional Journey

When I decided to make my side-gig my full-time business last year, I launched myself into a challenging emotional journey. While I knew I was signing up for hard work—I regularly wake up before sunrise and work 14 hour days through the week and on weekends—I wish I knew beforehand how to manage my emotions and calm my fears.

Here are some of the main emotional challenges I’ve had to deal with and the things I’ve learned about how to cope with them.


When I made the decision to leave my full-time job, I was terrified that I’d be alone and that I would miss out on valuable learning opportunities and mentorship. Not to mention, there would be a void in my heart for team-building events and company happy hours. This fear almost stopped me from taking the jump altogether.

To make sure what I feared wouldn’t come true, I have created as many opportunities as I can to work with my clients in person and to socialize with them. Since I live in San Francisco and my client “hotspots” are New York and Los Angeles, I schedule regular work travel to those cities. This has allowed me to meet 19 of my 25 clients. It’s also given me the opportunity to join many of my clients on happy hours.

On top of the effort I make with my clients, I also focus on building relationships with fellow freelancers. I’ll team up with them on projects and socialize with them.

My other loneliness fighting activities include working out of a shared office space three days a week and spending a third of my week on the phone or on Skype.

Needless to say, I am never lonely and actually appreciate my down time.

As for mentorship opportunities—going freelance has opened me up to lots of great relationships I never would have had before, including some of the top business leaders in my field. The chance to learn from them has been invaluable.

Identity crisis

When I first started my content business, I would ‘take anything and everything.’ I was genuinely excited about the freelance world and what it had to offer. Even more importantly, I thought that being a ‘jack of all trades’ would be a strong value proposition.

I was wrong. I had an awkwardly long elevator pitch and had a tough time branding (and consequently growing) my business. It was incredibly frustrating, and I constantly felt like I was floundering. At times I wondered whether I should keep going.

I kept struggling with painful doubts until I realized that my emotions were all over the place because my business was all over the place. Things would only settle down for me if I could find a clear focus for my business.

To find that focus, I made a list of (a) what I enjoyed most and (b) where I thought the market was growing. This exercise helped me see, in plain and simple terms, where I should be branding myself and focusing my company. As a result, I chose to specialize in producing customer education content for B2B SaaS technology startups.

From a business point of view, this focus has worked wonders. I have been able to grow my customer base to include some of the top technology companies in both Silicon Valley and Silicon Alley. From an emotional perspective, being focused has helped me conquer the doubts. I know what my business is, I can confidently and succinctly tell people what it is, and I believe in it.

Freaking out

Perfectionism is my arch nemesis. When I mess up—miss a deadline, forget to respond to a client, or encounter a frustrating situation—I am really, really tough on myself. I want everything to run smoothly, and my gut reaction (like any dedicated entrepreneur) is to freak out when it doesn’t.

The biggest lesson that I’ve learned as a solopreneur?

Take it easy. My best will always be my best—my clients are human, understanding, and wonderful people. What I’ve learned is that there is always a path forward, and oftentimes, my worst critic is myself.

I’ll admit that I’ve had a few big freak-outs since becoming an entrepreneur. I’ve lost my temper at loved ones (shamefully), cried, and have had days when I have felt like I’m totally failing. Oftentimes it’s little things—the worry that I won’t be able to make a deadline or feeling like I should be producing work faster. While I’ve never messed up anything major, I have had moments of miscommunication. And those moments really add up.

Dealing with my freak-outs has not been easy, but I’m getting better with the process. The solution has involved (1) recognizing my problems and (2) dealing with them head-on. After talking to fellow founders and yes, counselors who deal with entrepreneurs, I’ve realized that my challenges aren’t the end of the world. The sky isn’t falling, and I’ll always be able to find a constructive path forward. It’s up to me to create it. And sometimes, I’ll mess up. But that’s okay.

Self-forgiveness is something that I practice every single day—and it’s not easy. I have a never-ending list of things to do, and I constantly strive for ‘awesome.’ Every day is a challenge, but every day gets easier—the ‘little things’ are starting to feel less big.

Ask me in six months, and I’ll let you know how this process works.

Final thoughts: Design your worldview

I’ve learned that success is in my hands—that I have control. There will be ups. There will be downs. Ultimately, I need to embrace the bigger picture by staying committed to a long-term view—by learning from the emotional journeys of others who have been there before, learning about myself, and taking steps to keep emotions in check.

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