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  • Writer's pictureJenny Henderson

LESSONS FROM MY FIRST YEAR IN BUSINESS - Advice for running an online business

Updated: May 22

Everyone’s first year in business will look a bit different. While I’ve been a designer for a few years now, I’ve only been running my online branding business full-time for one year—and what a year it has been. As an online business owner, there are a few lessons I’ve learned that I hope will better prepare anyone running a service-based business from home.


Let’s start by saying there is no right way to run a business. There is only the way that works best for you. And yes, there is a learning curve. In the beginning it’s a lot of trial and error and that’s okay.

I would certainly recommend creating systems for yourself to keep you organized, especially with your clients. The more efficient your client processes, the stronger their experience will be (and the higher your referral rate).

You can achieve this with software like Asana or Dubsado or just a slew of spreadsheets—whichever you’re most comfortable with. I use Notion for client management and workflows and have many spreadsheets for tracking payments, expenses, and social and web analytics.

While that’s a good place to start, decide what you can and can’t handle. If tracking your expenses and earnings is something you struggle with or just plain hate—outsource it. It will allow you to focus your energy on the things that truly matter to you in business.

Just remember, there’s no right or wrong way, just adapt as you go to what works for YOU.


I pride myself on my organizational skills which I’ve inherited from my mother and am validated by way of Monica on Friends.

Google Calendar is my virtual assistant and I rely on her to stay on top of things. Any task, appointment, phone call, or even simple reminders all go into my calendar. I do this because I’m very forgetful but it allows me to see at a glance what I have to do so nothing falls through the cracks.

How I manage my time has been a work in progress. The biggest takeaway after a year of running this small business is to give myself more time on tasks. I found that, despite being thorough about scheduling my tasks, I was often bumping tasks to the next day or later in the week because a previous task took longer than I allotted.

Word to the wise: always schedule yourself more time than you imagine a task will take so you can actually stay true to your schedule.

Pay attention to the work you do that brings you the most joy


It took me a while to figure this one out but it is a game changer. It’s easy for us small business owners to put everyone else’s needs ahead of our own. But you need to remember that part of running a business successfully is developing your own business and working towards your own goals.

You can think you’ll find the time to focus on your own business, but chances are you’ll always prioritize client work. Sure, they are the income-generators but, if you aren’t working to grow as a business, you’ll fail to increase your prices or generate new leads.

Choose a day of the week or chunks of time throughout the week that are designated exclusively to your own business. Schedule it in your calendar like you would a client appointment and make it recurring. What are the benefits?

  • It allows you to schedule client work around your own business development

  • You can recharge from the (sometimes) gruelling demands of client work

  • You’ll feel more fulfilled by working on personal projects

  • It reminds you why you started your online business in the first place

  • You’ll be motivated and inspired when you return to your client work

Go schedule this time now—like right now.


This is one that I had heard many times before actually taking it seriously. I think you need to get burned first to realize the value of this. To run a successful online business you need to set boundaries and make them known. Clients can’t know what they don’t know.

I suffer from, what Oprah likes to call, the “Disease to Please”. As a result, I was always dropping anything to deliver a clients last-minute request or respond to an email. The thing is, if you do this once, you’re telling them this behaviour is okay. But if you set the expectation from the beginning, they’ll respect the process.

So now, in my client intro packages and contracts I make it known that I work Monday to Friday 9-5 EST and that Tuesdays are reserved for my own business development. This is important especially if you have clients in different timezones.

I also ensure it is communicated that I don’t respond to emails on the weekends. I had to turn off my email notifications on my phone because I can’t help but feel the need to respond right away (mostly because I’m forgetful and if I don’t do it now, I won’t remember until three days from now). Out of sight, out of mind. All emails can be dealt with on Monday.

My client contract has seen many iterations since I first started my small online business last year. My latest addition includes a penalty fee for unresponsive clients. This ensures my own project timelines are kept on track and I’m not jeopardizing other client projects due to a client ghosting for several weeks.


You’ve probably heard people telling you to find your niche or to niche down. If you haven’t determined your niche yet, that’s okay. Your business will evolve naturally. How I started my business last year compared to what it looks like now is very different.

In the beginning, I wasn’t just focused on branding, I was hired for all types of graphic design projects: lead magnet design, website wireframes, social media graphics, you name it. And don’t get me wrong, I loved doing all of those things and it allowed me to have a steady flow of client work.

But as the year went on, I eventually whittled my services down to focus on brand design and strategy. It wasn’t my intention when I started my business to be exclusively a brand designer, but I realized that it was those branding clients that gave me the most joy.

Pay attention to the work you do that brings you the most joy. Make note of it, look for a trend and I’m sure you’ll see that that’s where you do your best work. Find a way to niche down to the things that mean the most to you and your business will be better for it.


You can’t expect others to invest in your business if you won’t invest in your business. How you show up in your business will determine how it succeeds.

The reality of running your own business is that there are a lot of upfront costs, so it can certainly be hard to justify dropping another chunk of money on something even though you know it will better your business.

Recently I put quite a large sum down on a course that I know will be worth every penny in return. It will allow me to bring more to the table for my clients so they can build stronger, more sustainable businesses.

Why did I do this?

Because I whole-heartedly believe in the power of brand strategy to empower a business and I want to ensure I can deliver as much value to my clients as possible.

That’s how I invested in my business but another example for you might be professional branding. Branding is an investment in your business. Many of my clients come to me to rebrand their existing biz because they had hired someone to do a quick logo early on. But, of course, the logo served no real purpose in their business nor did it solve any problems for them or work towards their goals.

The thing is, when you invest in things the right way the first time around, you actually save money—not to mention, time and energy.

If there’s something you’ve been thinking about investing in but are having a hard time taking the leap, I would encourage you to imagine how your business will be different after you’ve made the investment.


In the world of entrepreneurship, there's always more to learn. Beyond courses and workshops you can take, be sure to carve out time to read, watch videos, listen to podcasts and just immerse yourself to learn more.

I recently made Friday mornings my time to read new articles and keep myself up to speed with brand strategy and business development. It keeps my inspired, sharp, and allows me to bring more to the table for my clients. Make it something you look forward to doing and always be learning!

These are just seven lessons I’ve learned running my online business this past year. It has been a work in progress and I am always grateful to be able to do what I love each day. My final piece of advice would be to look to those who are ahead of you in your industry for guidance. Chances are they’ve been where you are and are more than happy to share their own advice with you. The best part about running an online business is the community at large. You can connect with others in business just like you, forge meaningful connections with clients and customers, and grow your business all from the comfort of your living room.

strategic brand planner


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