Small Business Week: The Lessons We Learn Along the Way

Starting a small business is an education in itself. Beyond delivering a great product or service, entrepreneurs must learn to market their work, manage finances, build relationships, and navigate the unexpected.

For Small Business Week, we asked fellow business owners and experts to share the lessons and experiences that have shaped their businesses. From digital services and design to sales, counselling and healing, each brings a unique perspective on what it takes to build and sustain a business.

Meet the contributors:

• Daria Astanaeva, Founder of The Sell Well

• André Bussanich, Founder of Dos Dos Design

• Ishana Debba, Osteopathic Manual Practitioner and Kinesiologist at BOOM Healing

• Emily Macdonell, Owner of Emily Macdonell Counselling

• Paige Strand, Owner of Strand + Strategy Communications

• Ray Wang, Founder of RW Digital

What’s one thing you wish you knew before starting your business?

Daria: That the things that come easiest to you are usually the things people will pay you the most for. For years I thought selling and creating content was nothing special. It felt so natural that I didn't even see it as a service. I kept looking for the "real" thing to build my business around, when the money was in what I was already doing without thinking. Now I see it with every single one of my clients: the area where they make the most money is always the thing they think anyone could do. It's not. It's your genius, and you're allowed to get paid for it.

André: That good work doesn't sell itself. I spent years with my head down, assuming the work would speak for me, and barely showed any of it publicly. People can't hire you for work they've never seen. Now I treat sharing myself and the work as part of the job, not an afterthought.

Ishana: When it comes to marketing, you're advertising more than your service. You're promoting all you have to offer. It comes down to fostering valuable relationships with both patients and other health care professionals. You have to advocate for yourself and be discerning of who you choose to connect with based on your values around healthcare. 

Emily: I'm a therapist, so when I started my private practice, I spent a lot of time preparing for the therapy part of the role. What I didn't fully anticipate was just how much goes into actually running a business! I wish I had been better prepared for the other side; the marketing, accounting, systems, and other business-related tasks they certainly didn't teach us in grad school. I've learned so much along the way, and I'm still learning every day, but having a stronger foundation in the business side of things from the beginning would have made the transition so much easier.

Is there a tool or software that you swear by that you wish you knew about earlier?

Daria: Notion, paired with Claude. I run my entire client delivery out of Notion, and using Claude as an operations partner has completely changed how much I can handle with a lean team. Things that used to take me hours, like organizing client projects, drafting proposals, and keeping track of every moving piece, now take minutes, instead of keeping everything in my head.

Emily: Jane App! It's been a lifesaver for my small business. I save so much time and energy that I can instead dedicate to supporting my clients. Clients can easily self-schedule appointments, and Jane helps streamline everything from billing and accounts to day-to-day practice management. It's incredibly user friendly. I can't recommend it enough!

Ishana: To track finances and tax preparation, I really like Excel. It's straightforward and I can adjust sheets as needed for different purposes. Recently, I discovered Adobe Express, which is amazing for content creation.

André: AI, but for the boring stuff. Starting my own business forced me into AI and explorations with different agents. I use Claude for proposals, planning and admin, the things that used to eat up my evenings. I'm skeptical of it as a replacement for design thinking or brand strategy, but for operations, it frees me up to spend more time on the actual work.

What’s one thing that has made the biggest difference in your business?

Emily: Community. We need each other! Entrepreneurship can often feel like an isolating solo sport, so having people to connect with has made a huge difference. Community helps make the challenges feel manageable and the victories that much more meaningful. I've learned so much from the experiences, perspectives, and expertise of others, and I hope to offer that same support and knowledge when others need it (Emily also talks about this in a blog post about collective care).

Daria: Asking. Asking for the sale, for the price I actually want, for the clients I want to work with. As women, we're trained not to be seen as greedy, so we stay small and wait for someone to notice us and offer us what we deserve. When I stopped waiting and started asking every single day, everything changed. And getting paid what you're worth isn't greedy. It's what lets you invest more in your family, your community, and your life.

André: Leading with strategy before design. Every project starts with a workshop on purpose, personality, people, and positioning before anything visual gets made. The design ends up sharper, and clients understand why it looks the way it does.

Ray: We shifted our services by focusing on specific technical services and businesses of certain sizes. This focus helps us deliver more customized services to our clients and improve our efficiency.

Ishana: Being open and honest. Cliche, maybe, but it's true. I will always encourage asking questions and answering to the best of my knowledge. If I don't know something, I say that too. This builds trust and rapport that leads to retention and quality referrals.

What advice would you give someone who is thinking about becoming an entrepreneur?

‍Ray: Pick a career you’re truly passionate about or interested in. Entrepreneurship is challenging and can be dry and unsatisfactory in the beginning. Only passion can help an entrepreneur push through the initial slump.

Paige: I hesitated initially to start my business because I believed I needed to have all of the answers and tools ready before I could start. I thought “If I don’t have a website or accounting software set up, then it’s not perfect and I’m not ready,” when starting actually looks different for everyone. We don’t have to have all the answers right away. I would also recommend pre-socializing ideas with industry peers to ensure what you are bringing forward will actually work and bring value for your target clients.

Daria: Start building your personal brand before you need it. When my business fell apart, the only thing I had was the audience I had been building since 2022. I had no new money coming in, so I picked one woman I really wanted to work with and posted Instagram stories every single day speaking directly to her problem. Three weeks later she signed, and so did two other clients with the same problem. And please, don't stop because of what people think. When I started posting, someone I thought was a friend told me my content gave her second-hand embarrassment. I almost quit. I'm so glad I didn't.

What’s one little must-have on your desk that makes your workday smoother?

André: A sketchbook and a pencil. For me, every idea starts on paper before it touches a screen.

Ishana: I have different gems, rocks and crochet plants. They are reminders to be grounded and present while appreciating the individual beauty of each stone. It reminds me of the importance of connection and to meet people where they are at. 

Emily: A needoh sensory fidget toy!

Paige: Creatine gummies and inspirational quotes pinned on the wall beside me!

Daria: For me it's having my daily cappuccino with creatine and collagen before I start the workday.

Ray: A cute plush doll!

Learning from one another!

‍Every business takes a different path, but many of the lessons are shared. From recognizing the value of existing strengths to investing in community and asking for opportunities, these insights highlight the importance of learning as a business evolves.

This Small Business Week, consider reaching out to another entrepreneur, sharing a lesson learned or supporting a local business. Sometimes, the most valuable resource is the experience of someone who has been there before.

What better way to celebrate Small Business Week than with a virtual fireside chat with personal stories, group discussion, and a short nervous system reset you can take with you?

Hosted by Paige Strand and Body Intelligence Coach Christianne Zurowski, if you’re an entrepreneur who has ever thought “Why am I so overwhelmed?” or “I feel like I’m doing this all by myself,” this conversation is for you.

📅 October 21
🕛 12–1 p.m. PT
💻 Online