One Year into Full-time Freelance, Here's What I've Learned

Last September, I committed to making The Homegrown Studio my full-time job. A year in, I can say that this has been the fastest, craziest, most challenging, and most fulfilling year of my life, and I’m not looking back. Last September almost feels like ten years ago when I think of all I have learned, and the good news is that I feel like that shows most of all in the work I’m producing now.

I had shared some of the lessons I’d learned in my first month of freelance life, so I thought I’d take this opportunity to reflect now on a few key things I’ve taken in during a whole year of The Homegrown Studio. 

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1.     How to make connections.

 I talked about this a lot last time, but it still holds true and is still the single most important element to the success of my business. Pushing myself to meet people in-person and genuinely get to know them has been essential for gaining and keeping clients, but more importantly it has given me the opportunity to be part of a community that is full of amazing people, valuable resources, and fulfilling experiences. Sticking my neck out there was hard at first, but now it’s just something I require and expect of myself. I set a date, put real pants on, get in the car, get a stomach ache on the drive over, awkwardly locate the person I’m meeting, engage in an interesting and inspiring conversation, and leave saying THAT WAS THE BEST MEETING OF MY LIFE. Then I drive 100 mph back to my studio to sketch out ideas and send a note of thanks. It’s always, always, always worth it.

 Also! Ladies Drawing Night is going better than ever. Created with the sole purpose of meeting cool, creative people IRL, it has served that purpose and more. Thank you, thank you, thank you, to everyone who has bravely come out to join our little group each month. I still get a stomach ache every time I leave the house, always have an amazing time drawing and chatting, and wake up the next morning feeling energized and excited about the women I met.

 Bonus tip: when you do meet people, no matter where or who, tell them about what you are doing! Whenever I’m heading to an event or meeting or even a family gathering, I make a mental list of the big projects I’m working on right now so that they’re on the tip of my tongue. People are interested, and you never know what it might lead to!

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 2.     How to make money and manage it.

 Money has taken on a whole new presence in my life since I said goodbye to the regular paycheck twice a month. There were months where I barely made enough to pay the bills. There were months where I raked in more than $12,000. There were new, large bills to pay, there were Quickbooks to routinely screw up, and there were hefty taxes to fork over. The good news is, through prosperous times and plain old loss, it all evened out. I am on track to nearly double what I was making at my full-time corporate job at the end of 2019. I’m not bragging; I’m letting you know that this is all very doable. This is the tangible result of a lot of hard work and careful management.

One of the hardest parts was learning how to deal with the finances, and I’m still figuring it out. I hired an accountant as soon as I could afford it, because I knew this wasn’t exactly in my skill set and I wanted to do things right. I wouldn’t do well in jail. My accountant helped me understand how to pay my self-employment taxes quarterly, explained the correct way to pay myself, gave me a crash course in Quickbooks, showed me how to reconcile (I should really do that), and more.  I asked so many dumb questions, twice sometimes, and she was always patient and informative. I’m feeling much more comfortable now. 10/10 would recommend.

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 3.     How to streamline my process and become more efficient.

 I love working for myself, but sometimes I could really use an extra pair of hands. My cat does not have hands. Hiring help is not in the cards just yet, so something I really had to work on was my process, and finding where I could save myself time and effort.

 I’d say I really hit my stride with this in late spring. I completely standardized my client on-boarding process, vowing to never waver from it, even if my own mother needed a logo (turns out she does, by the first week in October). I created several presentation templates that are on-brand, display my work beautifully, and are easy to use and reference for clients. I created a file system that isn’t a complete embarrassment, and have regular deadlines for the reoccurring monthly tasks that must be met at all costs. This is all stuff that is easy to get bogged down in, but once I took the time to really streamline it all, I found I had much more time to spend where I ought to be: creating brilliant work for clients (and sometime for myself!).

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 4.     How to get clients saying YES.

 I hit a big rut in the depths of winter, and felt like I was banging my head against a wall. I had a full schedule of clients I was excited about, who had hired me because they liked my work and style, but repeatedly, my logo concepts were being rejected. They all appreciated what I’d come up with, but for one reason or another, it wasn’t what they’d had in mind. I deeply questioned my abilities and whether I could handle all this critique. And, going back to the drawing board so many times really backed up my schedule, pushing back deadlines again and again. I needed to take a hard look at what was going wrong here.

I talked to a lot of fellow designers about this, took part in an AMAZING workshop with the Hoodzpah gals, and concluded that I needed to put a lot more effort into two things: discovery, and selling my work. Discovery is the marketing research work that takes place before any designing happens, and while I was doing a little of this already, I wasn’t diving in nearly deep enough to make sure my designs met all expectations. Now, I include a thorough Discovery Meeting and Discovery Presentation in all of my branding packages. As far as selling clients on my designs, I knew I could do more there. I invested a lot of time in creating professional, engaging presentations that showcased the value of my work, explained my process, and allowed my designs to really shine. I learned how to speak about my work with confidence, and defend it when anything came into question.

 This has all made me much more deliberate about the design decisions I make, and ultimately it’s pushing me to create better brands. I’m happy to report in the last four logo concept presentations I’ve submitted, every client has chosen Option A (always my favorite, shhhh…) with little to no revisions. You can bet I am breathing a sigh of relief, and I can’t wait to share some of my strongest work yet!

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 5.     How to balance work and life.

Work and life balance, whatever that means, was something I was really grappling with my first month into freelance, and for a while after. It’s something I still think about a lot, but do feel like I have a much better grasp on what feels right.

 In the beginning, I was having a lot of trouble sleeping because I was thinking about all the things I needed to do. I was excited about work, but I couldn’t shut it off. I never knew if I had done “enough” at the end of the day, and there was certainly no one to tell me if I had or not.

List making was the savior here. I’ve always believed in writing things down, but now I’ve taken it to an extreme. Each morning I write a list of everything I’d like to work on that day, and each evening I write a list of things I need to follow up on tomorrow. Even the smallest of tasks. This empties my brain sufficiently; I can leave it on the paper. Each Friday, I write down a list of my accomplishments for the week, and the big objectives I need to focus on next week. I find this weirdly satisfying, and feel like I can stop working for the weekend – I’ve done enough. I do not work on the weekends. There have been a few small exceptions, but I do whatever it takes to keep to this rule. I feel great about it.

I’m very fortunate that work and life are beautifully intertwined, my passions commingling happily and creating interesting tensions that I’m inspired by over and over again. Whether it’s digging in the garden and incorporating sketches gathered there in a logo, or spotting a particularly lovely typeface on a weekend excursion, or noting the color palette during a trail ride, I’m so lucky that my daily experiences can so often be translated into my work. Freelance design has allowed me the time and space to make a living out of these moments, and I’ll sure be grateful if I get to do it for another year.

Photos by the amazing Jennifer Bakos Photography

One Month Into Full-Time Freelance, Here's What I've Learned

As of today, I’ve officially been calling The Homegrown Studio my full-time job for one whole month. Making the leap to freelancing full-time has been exciting and sometimes uncomfortable, but ultimately I can say I am feeling a whole lot better, happier, and more fulfilled than I was a month ago. Heck, I’m even making money. I’m surprising myself in new ways every day, and thought I’d share some of the things I pushed myself to do as I set out on this new chapter.

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1. I asked people to tea. (I don’t drink coffee!) The first thing I decided to do when jumping fully into freelance work was to turn the networking way up. I did this for two reasons: 1.) I felt in need of advice and work and ideas, and 2.) I was terrified of being lonely - about two days into freelancing I realized that this could easily get very lonely. So, I reached out to mentors and smart ladies I’d met along my career path and asked if they would meet up with me. They had nothing but great ideas and sound advice, and it was great to catch up. I threw invitations out to local people I admired and was curious about, but had previously only made contact through mere Instagram likes. Why stay behind the screen? I gained new perspectives and new friends in this case, which was so exciting. Here’s the awesome thing: no one turned down my invitation. Everyone I had tea with seemed genuinely happy to sit down and chat in person, and real, engaging, pleasant conversation always resulted.

2. I started something new. Out of this urge to connect with others originated the idea to bring a Ladies Drawing Night to Western Mass. I put the idea out there, set a date, found an awesome host, started an Instagram account, and put up posters. I was thrilled to see tons of women I barely knew were excited about this, and said “see you there!” it’s been fun learning how to make a community event happen and create all the branding around it as a neat personal project. I can’t wait for November 8 when we can all just meet up and draw!

3. I set measurable goals. At my corporate job, the practice of setting clear and measurable goals was hammered into me. It could get annoying, but there’s no denying it consistently worked.  Freelancing, I found myself going back to that ritual and making lists to prioritize tasks for the day, week, and month. Every Monday, I identify one thing I nailed last week, and three things I absolutely need to nail this week. Long term, I’ve started thinking about where I want to be in a year – three years – and I’m setting a timeline as to when I need to achieve smaller goals to make it all happen. I’ve been trying to stay disciplined about this, even as I’ve thrown a lot of my corporate structure out the window.

4. I reached out to dream clients. I’ve realized quickly how important it is to be cultivating new opportunities even as I’m working on the here and now. When I was freelancing by moonlight, I could kind of get away with being passive about this and rely on clients coming to me, no big deal if they didn’t. Full time, I really want to make sure work that I’m excited about is coming in consistently. I took some new tactics such as sending out postcards to people and businesses I would love to work with. I’m finding myself busier than ever, and with more of a plan to make sure it continues.

5. I set a schedule for myself. Well, still working on this one. The line between work and life has become blurry, although I’m loving the flexibility of working from home on my own terms. Knowing when to sit down and do nothing but work, when to run errands, when to go to the barn, when to visit my grandmother, when to schedule meetings with clients, and when to watch American Horror Story with my boyfriend has been challenging. I wonder at the end of each day did I do enough? I’m finding it difficult to shut off my brain and relax, something I had no problem doing with the corporate job. Setting those measurable goals has helped with this, and as I get a feel for this new lifestyle I’m getting a better picture of what ‘normal’ looks like, and when enough is enough. It’s an adjustment, and something I suspect I’ll always grapple with as so many other freelancers have advised me.

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There are still plenty of things I am wrapping my head around and learning (Quickbooks anyone???) but I’m feeling pretty darn good one month into the game. I am thrilled to be able to finally devote myself fully to my dream, focus my work entirely on my clients, and give this my best shot. I’ll update you on how it’s going at six months, and in the meantime, just let me know if you’d like to get tea!

Ladies Drawing Night Western Mass

I’ve been feeling like talking in real life with other local creatives; exchanging ideas, learning about others’ processes, getting feedback, and enjoying a laugh together at all of this. I’ve long been inspired by the original Ladies Drawing Night movement in Brooklyn, and loved the book by Julia Rothman, Leah Goren, and Rachael Cole. So I put a little idea out there on Insta, and was thrilled to see an enthusiastic response both from people I know and don’t know, and local businesses offering to host. I fleshed out the idea a little more from there and came up with Ladies Drawing Night Western Mass.

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The first LDN will be Thursday, November 8 from 7:00 - 9:00 pm at Holyoke Hummus in Holyoke, Mass.! It will be a fun, casual atmosphere for local creative women to make some art, share ideas, get inspiration, make new connections, and enjoy the best falafel in the Pioneer Valley.

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And, this will all be in benefit of the Holyoke Creative Arts Center, which provides low cost artistic instruction to the Holyoke community and beyond. They do a lot to support local arts and foster creative thinking in the community, and we’d like to show our support in return. Please consider donating when you come out to Ladies Drawing Night.

So, put LDN on your calendars, and I’ll look forward to seeing you on November 8! Can’t wait to meet you!