DIGITAL 55

STRATEGY_10 Things I Learned In My First Year As A Full Time (Badass) Entrepreneur

I always knew that I wanted to be my own boss. From a young age, I had a very creative and entrepreneurial spirit, and through all my years working for various companies, I always had a number of side businesses that kept my entrepreneurial spirit nurtured and my creative juices flowing (and extra income coming in!). 

When the agency I was working for went bankrupt last year, it felt like being pushed off a career cliff. But in that moment, I saw an opportunity and knew it was my time to take the next step and elevate myself and my career (and, you know, take over the world). 

Tapping into the strong relationships and deep trust I had cultivated with clients at that company, I was able to transition many of them into Digital 55 clients and seamlessly carry on doing awesome work. In doing so, I set myself up to launch my own business with a roster of clients, startup seed money, and an exciting project portfolio and production schedule ahead. 

 This first year has been a whirlwind of excitement, challenge, deep personal growth, and a lot of learnings and takeaways, many of which I had to learn in real time and as gracefully as I could manage. Here is everything I have learned in my first year as a full time entrepreneur: 

1. Ask for funding before you need it 

Did you know you don’t have to make it all happen on your own? You don’t have to liquidate all your personal assets and every worldly thing you own to start up. Depending on the country, province or state, and city you live in, there are a number of grant and loan opportunities available for small business owners. Don’t be afraid to do some research, ask around, and get applying! It can feel overwhelming at first, but accessing funding early on can set you up for success in stabilizing and growing your business as well as give you the freedom to seek out projects you love. 

2. Cash flow is key (and how to manage said cash flow) 

When numbers aren’t your strong suit (or even if they are), managing money can feel extremely overwhelming, especially when you are busy wearing multiple hats all at once. In your first year as a business owner, you may need to manage large sums of money, experience late-paying clients or contract terms going sideways, and have to pay out subcontractors or staff members. Know that there are many resources available to you to help with this transition (like apps, accountants, and advisors), and don’t be afraid to ask for help. Building a model of expertise for managing your business financials is something to do from day one. 

3. “Setting up” never really ends 

In the first year of your business, you can expect to tinker with things a lot. You will change your website, your branding, your business model, the way you write contracts, the way your business is registered, your style as a leader, and so much more. Trust that launching a business is an ongoing process and as it grows, you will have to throw away the concept of “done” and stay on top of what growth and change means for you. Try to enjoy the process and stay curious! 

4. Take care of yourself 

Your workload and pace of life is most likely going to be all over the place in your first year, so it’s important to keep a routine to maintain your physical, emotional and mental health. Try to get in a good groove with fitness (yoga, boxing, whatever works for you), eating healthy (and at regular times), and going to bed at the same time every night. These things may seem small and obvious, but squeezing in a workout or pausing for lunch (and actually chewing your food), will help keep you sane in the long run. 

5. Set boundaries with loved ones 

As your business grows, your time will become more valuable to you. Managing your new schedule and demands on your time, may make things more difficult when it comes to managing the close relationships in your life. It’s important to set clear boundaries with friends and family in order to protect your space (and your sanity.) This may mean your relationships will change, and you may face some pushback from your loved ones, so be sure to remind them how much you love them while authentically asking them to support you in your new normal. 

6. It can get lonely 

Running your own company comes with a lot of emotional ups and downs. At times, you’ll be making some very “grown up” decisions and taking on ginormous risks that can feel very scary. This pressure can feel overwhelming, which is why it’s important to build a strong professional network. Work with a business advisor or coach, an accountant, and network with other entrepreneurs to remind you that you aren’t alone in this journey. 

7. You’ll have to manage a team 

Whether you’re experienced with managing a team or not, it’s a whole different ball game when it’s your own business on the line. Because my business model is a decentralized one, meaning I subcontract a group of remote freelancers and some key retainer talent, I have learned to navigate a new role as a leader to a distributed and remote team. This new position comes with its own share of interpersonal challenges, but the flexibility of my business model allows me to work with people I connect with professionally, personally and creatively and in a highly curated way. 

8. You’ll have to manage your clients too 

Your relationship with your clients can grow to be quite intimate very quickly, and it can sometimes even start to feel like you are dating your clients! Fostering client relationships can become a bit of an art form (or a juggling act), in ensuring you are fulfilling the project requirements, collaborating and building together, and making them happy, while also protecting your creative vision, scope considerations, and personal space. Boundaries such as a hard stop on revisions or only responding to email during standard office hours will help protect and strengthen your relationship. 

9. Make time to learn and get creative 

When you’re in the thick of business development and focusing on getting client projects out the door on time, it can be hard to make time and space for creative projects or to invest in your own learning. Build time into your calendar to write, paint, read, sing, or engage in whatever creative pursuits help bring you back to reality, and always make sure you’re never too deep in the thick of things to take a class or attend a workshop. Ongoing learning keeps your skills fresh, helps raise your valuation, and allows you to meet new people and get a feel for what other brands, organizations, and industries are doing. 

10. Invest in strategy 

In your first year, your focus will likely just be keeping your head above water. You will likely be most concerned with juggling clients and stabilizing your income and revenue. But as time goes on and you become more comfortable, it’s wise to start investing in more strategic moves. Now going into my second year in business, my goal is to curate my client roster and focus on heart-based and innovation projects that allow me to get really exploratory and creative with new technology and experience design approaches that make a long-term impact on the world! 

When I became a full-time entrepreneur last year, there were a lot of things I wish someone had told me before I started. I learned as I went and made mistakes in real time which is scary when the runway for your company’s stability depends on your each and every decision, but I now feel far more confident and in control of my life than ever before — and pumped every day by the purpose of our work! By maintaining boundaries, protecting my personal space, and creating opportunities to learn and grow, I have been able to smoothly transition into my second year of full-time operations. What business lessons have you learned along the way? 

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