12 lessons learned from starting a creative business (months 1-3)


I started my design and coaching studio last fall— chipping away on it during early mornings before work and on weekends- but it’s only been 3 months since I left my job to do this full time. (Which was, by far, the best decision I have ever made). 

Since I try to be so deliberate about planning my goals, I see the review process as the closing of that loop. At the end of every month, I sit down to look at what I’ve accomplished, and I articulate the lessons to take with me as I continue to grow. Here’s what I learned from months 1-3: 

1) Take the most direct path to doing what you truly want to be do.

Don’t create extra work or hoops for yourself to jump through just to prove to yourself that you can do it, to get over your imposter syndrome, or out of an urge to feel like you’re “good enough.” This includes taking on clients for less than what you’re comfortable being paid for, or doing a bunch of work to help you “get ready” for doing the real thing. No. You’ll get over your anxiety by doing the kind of work that you truly want to be doing. (This wisdom was dispensed by a wise friend, Amy, after I told her about my infinitely complicated business plans).

2) Be prolific. Focus on making amazing work that rings true to you. 

At the beginning, you’re unsure of who you are as a creative, and freaking out about getting clients. Instead of getting caught up in that external cycle, focus on building a body of work that resonates with you. You may get nothing out of sending 10 cold emails, but your best work will always continue to serve you. People will be able to sense the work that is honest and true, vs. the work that panders to an audience. Slowly, you’ll see return on your investment. (This advice comes from my friends Brian and George, whom I both admire for their focus and ability to execute amazing projects). 

3) Keep it simple.

When approaching any task or endeavor, remember to ask yourself: how can I cut it down to its core essence? Whether it’s a presentation, communicating in session with a client, or bringing a project from idea to reality, ask yourself how you can simplify it. Then make it even more simple. Why? Simple things stick. Simple things are easier to make real, will give you the confidence to continue to refine it.

4) Work quickly and iteratively

This is especially relevant for perfectionists. Instead of getting caught up in making each step perfect, give yourself clear time blocks (1 day, 3 days, 5 days) and strict deadlines. When you have a presentation due for class, you forget about all the frills and hone in on what will have the most impact. Challenge yourself to cut a task down into its most basic, bare form - think version 1.0. Give yourself a hard deadline and stick to it. Then do version 2.0. Then version 3.0. With each version, you’ll build on the last and make something better. Do not get stuck. For more on this, check out Google's design sprints

5) Practice ultra-compartmentalization. 

Recognize when your attention gets fragmented by different types of tasks and the distractions in your day (email, social media, demands from other people). Think carefully about how to protect your time and energy. For instance, I notice that checking email before doing focused work will put a massive dent in my productivity. I like to compartmentalize by designating certain blocks for certain tasks, and setting a clear start/stop marker for what I’m working on. My early morning is reserved for personal design projects or writing, early afternoon is emails and social media, late afternoon is client work. Whenever I’m feeling fragmented, it’s usually because I’m trying to physically switch my attention too many times in a span of time. For more reading on this, I recommend Cal Newport’s book, Deep Work

6) Recognize bottlenecks and black boxes in your work.

Bottlenecks are the types of tasks that prevent you from moving forward. For me, I realize that I felt immense resistance towards networking events because I fixated on the fact that I didn’t have business cards. Bottlenecks are often logistical in nature and feel daunting— not having a name, a website, not being set up on a social media platform, so never posting on it. Black boxes are similar - these are the “unknowns” that can become bottlenecks. Black boxes are often decisions you put off making (where to host this site? what should we name it?) The danger is when it delays the entire projects, so it’s crucial to be aware of them and nimble about navigating around them. 

7) Systematize tasks that make you uncomfortable.

I used to get really nervous about emailing people, going to networking events, or posting stuff on social media. I’ve found that if I make a step-by-step list detailing exactly what I need to do (email specific 4 people this week, post 5 things online), I’ll reduce the friction and nervous energy that comes with doing them. If I do it regularly and have a clear benchmark for what constitutes “success,” I’ll slowly get over the inertia of doing uncomfortable tasks, and it will feel routine. For example: I get over my fear of networking events by going to one event a week, and my benchmark is making a connection with just one person at that event. Then I can go home. 

8) Plant seeds so that you can harvest later.

What do I mean by this? To grow a business, it will require that you nurture relationships, refine your brand, amass a body of work, and slowly grow into yourself as a creative and as a business owner.  My seed-planting includes writing this blog, sending newsletters, being on social media, meeting people for coffee, and working and sharing my personal projects. This kind of effort is so valuable, but you won’t see the benefits of it overnight. On the other hand, “the harvest” - suddenly getting emails from people who want to work with you, opportunities that seem to fall into your lap, the client who decides to come through - can happen at any moment. It seems mysterious, but after all that seed planting, you’ll realize that it’s not.

9) Relationships are the foundation of everything.

No one wants to feel used or sold to. When it comes to business, so much of it is about connecting with people honestly, and having them trust you enough to invest in you. I’ve noticed too many people who focus on the “sell” first, when it’s really the relationship that is at the core foundation of all opportunities. Focusing on the “sell” is like forcing yourself into someone’s home. Building human relationships is nurturing something that will last, and letting others invite you in. 

10) Putting yourself out there just means being proactive. 

When people say “put yourself out there,” it’s hard to remember what it actually, concretely means. It means being proactive about making new connections, and sharing yourself and your work in ways that may make you feel vulnerable (this is different from oversharing). For me, it meant putting up work on my website, going to events alone, reaching out to people to meet for coffee, and just showing up. Consistently. 

11) Have an attitude of ease and plenty, not scarcity. 

For a while, I felt like I was drowning because I never felt like I was doing enough to grow my business. I worried that I would never get clients, never get any work, and struggle to pay my bills. Then I realized: that attitude will drown me. It actually paralyzes me from doing the work. I was making it hard on myself by assuming that it would be hard. But why? Why does it have to be so difficult? Shifting my mindset to an attitude of ease and plenty was crucial to making me more productive, confident, and ultimately, more successful. It's the chicken and the egg question. Do you feel at ease often after you've achieved X, Y, or Z? I'll propose that the mentality comes first. 

12) Consistency creates momentum.

Many people about written about consistency as the secret to creating amazing work, and being successful in any endeavor. Consistency is showing up at the same time, doing the same thing, rain or shine. Consistency is not sexy. It is not mysterious. But when seemingly mysterious things happen— a perfect client or project falls into your lap, a book deal is offered, some major publicity piece is published about you— consistency is that force humming in the background, the thing we should give thanks to. 


Barely 6 months ago, I had no website, no portfolio, no plan, just 1 client, and nothing to show for myself. Just 3 months ago, I had massive imposter syndrome that struck whenever people asked me what I did, and I said, very self-consciously, that I was a designer and creative coach. Was I? Really? Says who? Sometimes that feeling still surges, but I don’t listen to it. I’m a designer and creative coach because I decided that’s who I want to be. And I’ll continue showing up. 


Thank you so much for reading. I help creatives and entrepreneurs get organized, build honest brands, and market themselves efficiently and effectively. If you'd like to chat, don't hesitate to email me.