Out of Office: First Month of Freelancing

It’s been just over one month since I started my Out of Office freelancing career, and this month has been full of highs and lows! I am beginning to really understand the entrepreneurship roller coaster. 

After returning from vacation, I dove straight into meetings and emails with potential clients. My first week back, I had so many proposals to send out that I was genuinely concerned that I wouldn’t be able to manage all of it if I got those projects. But of course, you’re going to strike out now and then. I had most of those proposals come back approved, but there was one big one that I didn’t get. 

To be honest, I don’t think that not getting that contract was a huge loss, but it was the sting of rejection that gave me a moment of major anxiety. After receiving that email, I was sure that I wasn’t going to make it as a freelancer, but then I remembered that this is month one and this is going to happen! 

Just as I was getting into the groove of the work a little bit, my family suffered a big loss and I lost a bit of momentum as I grieved with my crew. Absolutely no regrets for taking that time to be with family, but I did quickly learn that, as a solopreneur, if you’re not working on your business, no one is.

As I expected, the greatest struggle for me in month one was not taking time to be with family or taking a week long vacation – it was imposter syndrome. 

Out of Office: First Month of Freelancing
Photo by Danielle Serres Photography

I knew that believing in my skills and knowledge was going to be the toughest part, as this is something that I’ve dealt with a lot in my career. Lucky for me, I have Kirby giving me a firm talking-to when I fall into the self-doubt arena. 

Some wins from this month:

Some losses from this month:

  • Did not win on a big proposal that I sent out
  • Lost a client 

I’m into my second month of full-time freelancing now and I’m feeling motivated to fill up my roster of clients, complete a few projects and pump out some great content on the blog. I’m also feeling very grateful for the support that I’ve received from friends, family and acquaintances in this first month. I can’t wait to share more of my journey as a full-time freelancer!

Is there anything specific that you want to know about my Out of Office career? DM me on Instagram @sammmyhill or send me an email at sammy@sammmyhill.com to chat!

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