10 Things 2018 Taught Me About Building a Successful Freelance Business

Year in Review

2018 turned out to be a pretty great year for myself and Kate Winter Digital Solutions. I have experienced tremendous personal and professional growth, doubled my business from 2017 to 2018, and grown as a developer and as a creative individual. Building my freelance business has never been easy but has been an incredibly rewarding experience that I am grateful every day that I began. As this year is wrapping up and I am planning for 2019, I wanted to take a minute and share the lessons that 2018 has taught me. These are applicable to anyone building a business or a brand whether you are a freelancer, small business, blogger or entrepreneur. 

Adopt the moto ‘adapt or die’. Change is inevitable, accept that as early as you possibly can. A lot changed in how I work with my clients this year. By accepting that my clients’ needs change and my business needs to adapt with those changes, I have been able to add billable services to my offerings and I am of more value to my clients. The core work I do is still the same- websites and digital strategy, but I am able to be a better resource by adding graphic design and basic photography.

Keep learning. Systems change, design trends change, and available resources are always changing. Stay on top of the trends and the industry news that is applicable to you. Learn from new designers. See what other freelancers are creating. I check my competitors’ portfolios regularly. I want to see what my clients are seeing when they are looking to hire someone like me. Are my skills and designs relevant? Do I need to learn a new tool to help my clients better? Grow those professional skills!

Listen to your clients. When 3 or 4 clients asked for graphic design services, I got tired of farming out the work or recommending others. This goes back to ‘adapt or die’. Be the resource your clients need. Listen to them! Learning is not comfortable, but growth never happens in the comfort of your bubble. Get out and learn new skills or someone else will gladly do that work.

Invest in the tools you need, but don’t go broke. Don’t cheap out on the tools you need, you will regret it. I upgraded a lot of systems and invested in the tools I need to help my business succeed in the long run. 2018 taught me that this business is mine for the long run, and I will regret not upgrading some things sooner. You also don’t need super high end, remember, they can’t do the work for you. Because my background is in automotive, you don’t need a Porche to do the job of a Honda. Prioritize reliability and quality and you will be just fine.

Ask for referrals! The best thing I heard this year was ‘I was referred to you by ____’. What an honor that a previous client thought highly enough of my work and the services I provide to recommend me to a friend, family member, or fellow business. Asking for referrals is awkward at first but it doesn’t have to be intimidating or overly direct. One of my favorite methods is to add the request to your email signature or a follow-up email. Some clients even have a referral discount or reward, there is nothing wrong with incentivizing someone for a referral!

Don’t quit the day job… yet. Getting the figures and finances to line-up for ‘the big jump’ from side-hustle to full-time hasn’t happened yet, and that’s okay. I have the security of my job while I am building this business. The skills I have developed in my own business have actually helped me become better at my job. Time management will constantly be a challenge but I know it won’t always be this way and the extra hours are always worth it. If you are struggling with taking a side hustle to a full-time level, I highly suggest talking to an experienced financial planner and accountant before making any radical changes.

Work smart, not hard. Yes, hard work is important but efficient work is what gets projects finished. I can put together proposals in half the time I could a year ago. I have clearer processes for building websites that save me hours of work. Most importantly, I know HOW I work best now and WHEN I work best. Hack your productivity. Learn about your own working patterns. I personally need big projects broken up into chunks and I schedule those out. That’s how I work best. To figure out your own working patterns, find the times and environments where you are the most productive and replicate that. Oh, and working somewhere with weak wi-fi just for good coffee is never worth it.

Just keep going. Some days suck. Don’t let your mind stay there long. Tough clients, rejected proposals, creative differences, all happen. Find those friends or family members that can listen without letting you spiral down the drain of frustration. These are people who can remind you of all the great things you do and get you back on track. Remember, not every client is perfect for you. I learned very early in my freelance business that it is okay to gracefully turn away a client that is a bad fit. ‘Thank you for your interest, but I don’t think I am the designer for you. May I recommend someone I feel is a better fit?’ Whether it is the style, budget, scope of work, or just a simple personality difference- it is okay to not take the job, it is in the best interest of the client and yourself.

Give your self some credit. I have the hardest time with this. Self-criticism is my thing. I always find the one thing I’m not happy with before seeing 10 great things, but only in the things I create. This is where that support system really helps, I have those trusted people that remind me of what I have accomplished and will gently tell me if something is rubbish. Overall I really am happy with what I have done over the past two years and the end of the year is a great time to look backward before moving forward.

Rest when you need it, before you burn out. I took a 10-day vacation without social media, news, and email at the end of November. It was magical. The first few days without constant connection to my phone and laptop were difficult but I eventually relaxed. When I got back I was ready to work and my head was clear. And since then, I have been able to enjoy the holiday season not simply ticking off my to-do list and waiting for it to be over. I am enjoying the holidays and truly present with my family while still being productive for my clients. Getting my head in the right space before this busy season was important and I will take that lesson into 2019 by scheduling time away from technology.


Merry Christmas, Happy Holidays, and Happy New Year!