Betting on Myself: What I Learned in My First Year of Business

A year ago, I took what some would consider a huge risk – I left a job I didn’t love without a new gig lined up, and I started my own business.

Was it easy? Nope. Did it fix all my problems? Absolutely not.

But it was the greatest gift I’ve ever given myself.

Starting a business is not magic, and I truly believe anyone can learn how to do it. But that doesn’t mean it’s simple, either. Success comes from developing systems that work well with your strengths and tendencies while also minimizing common pitfalls.

Why I started my own business

It’s not a secret that many people are going into business for themselves right now. Why is that? For me, it was about aligning myself with bigger goals and pruning away aspects of modern-day work that just don’t serve me. In my pre-entrepreneur life, I was burning the candle at both ends, and most of the time, it wasn’t even for work I cared about.

Agency culture just wasn’t appealing to me – from working long hours against constant moving targets to demand for returning to offices full time while a pandemic that has killed millions continued to simmer in the background. By the time I left, I was tired, sad, and sick. And honestly, I just knew I could do it better – but instead for organizations with missions I respect and for the pay I deserve.

Part of it was also identifying a need. I’ve been involved in harm reduction and needle exchange for many years, and I knew several organizations that could benefit from websites and design work. I happily volunteered to help them, and some of them paid me – but ultimately, all of them were so excited to work with someone who was already part of the movement and had the skills they needed to build greater community awareness and increase access to resources.

From that need, I carved out a niche and established my guiding principles – I call this my North Star. I knew I ultimately wanted to build websites and brands for people and organizations doing justice-centered work.

How I overcame initial obstacles

I didn’t take the plunge into self employment immediately after quitting my job. I first spent some time anxiously searching for another job and questioning myself. Did I overreact? Was working in an office really THAT bad? (Honest answer: No, I didn’t, and yes, it was.)

I ended up applying to and interviewing for some promising gigs, including one that would have more than doubled my previous salary. But by the time I reached the final round of interviews for that job, I had already made up my mind to do my own thing. Taking myself out of the applicant pool brought on a lot of fear – I worried I would regret not taking the fancy, high-salary position, and to this day, I still sometimes wonder if I should have.

When I set out on my own, there were some obvious obstacles, a big one being money. I was terrified I wouldn’t be able to make enough to pay my bills. On top of that, my self doubt was in overdrive. I questioned whether I was cut out for entrepreneurship and grappled with worries about what other people would think of me if I didn’t succeed.

But I also felt immediate, intense relief when I started my business. One year later, I can confidently say my mental health is the best it’s ever been. Having full control over my time has allowed me the space to listen to my body, rest when I need to, and show up for my family and friends when they need me.

Betting on myself felt good. Like, REALLY good. Even though I was terrified by how all this would play out, I knew trusting myself with this important venture was the right and necessary thing to do.

How I kept track of my time and money

While I recognized it was important to give myself space to decompress from work, it was also crucial that I nail down a time management system that would work for me and keep me moving toward my business goals. Here are a few simple strategies and resources that helped:

On the financial side, I needed to establish a way for me to bill clients so they could pay me. I also wanted to ensure I kept my personal and business money entirely separate. Here are some financial tools I recommend:

  • Wave, Zipbooks, or Quickbooks for invoicing and accounting (Note: Quickbooks is not free, but it is worth the upgrade once you’ve established yourself)
  • Relay for business banking

Three mistakes I made in my first year

Like I said before: Anyone can learn how to start their own business. But it won’t always be smooth sailing, and mistakes are a given. I messed up plenty of times in my first year – so I’m sharing my top three mistakes here to help you avoid making them too.

  1. Not paying myself a designated salary

When I first started out, I did not establish a system to even out my feast and famine periods. For example, in my best month, I made $17,000, which is incredible. But then I had four months in which I made under $500. 

Initially my strategy was to pay myself 50% every time I got paid and reserve 20% for taxes and 30% for business expenses. It wasn’t until I read “Profit First” by Mike Michaelowicz that I learned how important it was to designate a salary for myself and only take that salary, regardless of whether I had a bad or good month. It helped me to smooth out peaks and valleys while also managing my feelings about money.

Sales page from Website in a Day
  1. Putting money behind an untested idea

One of my greater disappointments showed up in the form of a new offering I created called “Website in a Day.” The idea was to charge a lot of money ($4,800 to be exact) for a quick-turn, professional site. This stemmed from a challenge I was participating in as a member of We Should All Be Millionaires: The Club (I highly recommend the associated book and Hello Seven podcast by Rachel Rodgers.)

For the offering, I created a really sexy sales page and paid a brilliant copywriter $2,500 to write the sales page copy. I pushed marketing for 10 days, promoting the service harder than anything I’ve ever promoted before, with the goal of making $10k during that period.

I got zero sign ups. I felt defeated – after putting it all out there, talking to so many people about it, and asking my friends to share it on social media, all to just get…crickets. Despite that, I learned one incredibly valuable thing: My audience does not prioritize speed and won’t invest extra money for a quicker turnaround. This insight resulted in me creating one of my most successful services, and while the “Website in a Day” offering was a costly mistake, I now better understand the needs of my client base.

  1. Overwhelming myself with business and marketing content

This one may not seem like a “big” mistake – but I think it’s one a lot of new entrepreneurs make, probably unbeknownst to them. When I first began working for myself, I was consuming as much business and marketing media as I could get my hands on. While this was a helpful exercise, I quickly spiraled about the millions and billions of things I needed to be doing to achieve success and get the word out about my work.

So I scaled back my work-related reading. While I still consume business and marketing stuff – check out How I Built It, The Online Business Show, and Dare To Lead – I also pepper in fiction, podcasts about tarot, and activities that have literally nothing to do with my business and everything to do with my happiness. And to be honest, me being happy contributes a lot more to the success of my business than me being stressed.

What a realistic first year looks like financially

So, where did I end up landing financially after my first year? As you’ll recall, money was one of my biggest concerns from the beginning. 

All told, I actually took a pay cut of $17,626 compared to my old salary. But I have to say – the improvements to my mental health were well worth it. Here’s the breakdown:

  • During my first year, my net income was $23,180 ($31,614 in revenue minus $8,434 in expenses) 
  • I paid myself about half of the revenue, so I personally made $14,190 from the business in 2021
  • In Q3 and Q4, I supplemented my income by teaching at ASU’s Design School, where I made $12,000 during the 2021 fall semester
  • Adding in my income from my old job from the first two months of the year, I made $37,376 in total

It’s also important to acknowledge my privilege. When I left my job, I had a cushion of $8k in emergency savings. I also have an incredibly supportive partner with stable income who could afford to take over my half of the bills if needed. Having these safety nets allowed me a bit of comfort to take risks.

Profit & Loss Report generated from Quickbooks

What you can expect from me in 2022

I’m starting my second year of business feeling established and confident in where I’m headed next. My main priorities are twofold:

  • Making my work with clients and their experience with me simple and frictionless 
  • Identifying creative ways to support new organizations and movements in alignment with my values

I’m so excited for what’s to come and hope you’ll follow along. For more content on starting your own business, marketing in the nonprofit space, and designing with accessibility in mind, please sign up for my newsletter.