Discover How Jaclyn Westlake’s Break from Her Career Led to Freelance Writing Success

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Jaclyn Westlake is a San Francisco Bay Area-based freelance career advice and lifestyle writer. You can find her work on The Muse, Forbes, Business Insider, Fast Company, and The Bold Italic, and on her blog, The Wife Aquatic. After almost 10 years in the corporate HR space, she quit her start-up job and founded a small resume writing business. For the past four years, she’s worked exclusively from home (which happens to be a boat) with her dog, Indiana Jones by her side.

1) How did you get started working from home?

I started dreaming of working from home after braving an hour-long commute across the San Francisco Bay Bridge. I envisioned quiet PJ-clad mornings with coffee in-hand and productive, interruption-free days. But, I had no idea how to make that dream come to fruition. After reaching a breaking point at my start-up job, I decided to quit and take a couple of months to rethink my next career move. To keep busy, I wrote resumes for friends and family, which rapidly became a viable business and subsequently led to a freelance writing career.

2) How did you choose the work-at-home career you do?

I wish I could say my path was well-thought out and entirely strategic, but in reality, I pieced it together as I went. I started by re-imagining how I could use my HR and recruiting expertise in a different way, which turned out to be resume writing and career coaching. Writing career advice columns (and subsequently lifestyle pieces) then became a logical next step.

3) How did you get started (basic initial steps)? 

I built a simple, bare-bones website with a short bio and a list of services and fees. I then sent an email out to friends, family, and former colleagues to let them know what I was up to. I had clients lined up in no time! Which meant that I needed to come up with terms and conditions, client contracts and an invoicing system in a hurry.

4) How did you get your first client or customer or job? 

Networking helped me land my first client and virtually every client since then. I was very intentional about this part of my strategy and specifically asked my contacts to share my website (and later my articles) on their social media pages.

5) How do you market your business? 

I rely heavily on networking, social media, and proactive outreach. If there’s a publication that I want to write for, I’ll approach the editor with a well-thought-out pitch. But, I also get approached via LinkedIn and social media, too. I’ve found that putting myself out there in a visible, consistent way is the best strategy for sourcing quality opportunities.

6) What does your usual day look like? 

Most days, my alarm goes off at 5:30 am. I run out the door to make a yoga or cycling class and then come home for coffee and breakfast with my husband. We like to listen to a podcast together (usually The Daily or Up First) and then we start our days. My husband works from home too, so we’ll retreat to our respective desks and check in with each other around lunchtime. I’ll tackle emails first and then dive into whatever projects are currently on my to-do list. I’ll break for lunch around noon, take a shower, possibly run an errand, or take the dog for a walk (or maybe out for a quick kayak) and circle back to my desk around 2 pm. I’m usually able to wrap up by 4 pm – just in time to start prepping dinner or enjoy a glass of wine. Sometimes I’ll squeeze in a little more work around 8 pm if I’m feeling a second wind.

I also make it a point to head into the city to meet up with friends for dinner at least once a week so that I still get my social time in!

7) What do you know now that you wish you knew when you started? 

I have to stick to a schedule. At first, it was so easy to sleep in and let the day get away from me. I have friends who prefer to start their workdays in the afternoon, but I’m most productive in the morning, so I don’t want to squander all of that creative energy!

8) What advice would you give someone who wants to work from home? 

Be really honest with yourself about your work style. If you have a lot of distractions at home (kids, pets, chores, etc.) getting out of the house might be the key to your success. If you know you aren’t a morning person, don’t force yourself to work first thing in the day – you get to make your own schedule. And wherever you work – whether it’s from your coach or a coffee shop – make sure you have a designated space where you can be productive. It’ll take some trial and error, but you’ll get into a rhythm that’ll work for you eventually.

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