Here’s my soapbox: There’s no one way to build a successful online business. Every book and every blog post you read should be a practice in taking what you like and leaving what you don’t. Diversify where you get your business advice. Learn from people building six or seven-figure businesses (including some of my interviewees below) as well as those whose idea of hell is tying their success to an arbitrary financial metric.
The online echo chamber (hello social media, I’m looking at you) can make it feel like the blueprint for creating an online business is getting narrower by the minute while the advice and coaching programs swing between incredibly ambiguous (they never actually tell you how they did what they did) or incredibly rigid.
I don’t know about you, but I like real numbers breakdowns, real stories of success AND failure, practical tips and tutorials I can turn around and try out immediately. (And not resent the FOMO if I decide something’s not right for my business.)
That’s the kind of content I strive to serve up in my bi-weekly newsletter, Letters From Your Editor and in part why I asked four fellow solopreneurs (some I consider my life and business Board of Advisors) to hit me with their best practical and tactical tips annnnnd to spill the beans about their biggest setbacks and struggles.
My goal is to show you that there are many different approaches one can take when running a business and to hopefully inspire you with one new thought or idea you can take with you.
If you’re looking for diverse perspectives on what it’s like to run an online business 3, 4, and 9 years in, you’re gonna wanna take notes!
In case you missed it, this is the second half of my Solopreneur Series.
Click here for Part I: Secrets Of A Successful Online Business (a.k.a. Ask Me Anything!)
The Business Leaders
Carole Ann Penney of Penney Leadership
Years in Business: 9
Carole Ann is the reason this ‘lil bitty business exists . The origin story: I was struggling with my sense of worth and self-confidence as a result of an incredibly toxic work environment. I knew it was time to look for a new job but feared that the next opportunity would just be more of the same. Enter Carole Ann, coach extraordinaire for mission-driven leaders. I rediscovered my purpose and passion with Carole Ann’s help and the rest is history.
Verô Souza of Verô Branding
Years in Business: 3
Me: “Business owners always think of design first, never strategy or copy. I wish I could find some amazing designers who get where I’m coming from and could use it to create swoon-worthy work that turns purposes-driven businesses into brands. What’s this? An email from my 90DBL coaching alum group. This Verô sure sounds awesome. Maybe I’ll reach out…I hope I’m cool enough for her.” [Spoiler alert: I am NOT cool enough for her, but we’ve managed to rebrand and refresh more businesses than I have fingers and we’ve been partnered up basically since Day 1.]
Jessie Wyman of Jessie Wyman Photography
Years in Business: 9
After many failed attempts to convey the essence of my brand via my website imagery, I decided it was time to face my fears and be my own model. On a whim I put out a call on Instagram for brand photographers local to the Boston or Rhode Island area and the moment I pulled up Jessie’s portfolio I knew she was the only person I could trust to help me “show” my audience what brand strategy and copywriting looks like, without ending up with 500 generic shots of me typing on a computer. The bonus: Jessie runs multiple businesses and is always my first DM when I’m thinking about trying something new or struggling with my marketing.
Kate Hutcheson of The Efficient Creative
Years in Business: 4
Another 90DBL-er, I knew about and stalked Kate loooooong before I actually hired her to get my Dubsado sorted. Girlfriend is a Jane of all trades and has a Mary Poppins bag full of skills I **wish** I had the time to master. I had no idea when I started my business that I’d have to become so well versed in at least two dozen platforms. I don’t know how she manages to stay on top of so many systems and tools, but I imagine her mind is a very organized storage unit full of filing cabinets whereas mine is more like well-intentioned storage cubes that end up a right mess within a week.
The Interview
How many days a week do you work on/in your business?
CA: 7
VS: Many. At least 2-3 days.
JW: 5
KH: 5. I only work evenings or weekends if I really want to (or really have to).
Tell me a moment when you were like “I have no business/the audacity to do this thing” but you did it anyway and it turned out great!
CA: Recently I was asked to be a keynote speaker for a gathering of 500 political leaders. At first I thought, “ME?!? What could I possibly have to say?” But then I thought about how urgent and essential the needs of leadership are right now, and that this is an opportunity to share a very meaningful message. If I don’t do it, some mediocre white guy will be happy to take the air time. But I can share a message that actually sparks change. (Omg are you going to print that somewhere!?)
VS: This year pivoting into teaching visual branding for new small business owners. I had no idea if it would work, teaching is a whole new universe but I still did it because it blows my skirt up! The moment came after getting amazing testimonials from students who have taken my Bring Your Brand To Life course, seeing how brilliantly creative they are and hearing how they now feel confident and proud about their brand. BEST FEELING EVER!
JW: My first paid session as a photographer! I was at a point where I needed to charge because it was becoming more than just a hobby. But I was still like “wait, what?! Someone will actually pay me for this!?”
KH: I’m always struggling with coming up with content to write, but when a coach gave me a whole list of cornerstone content topics I needed to write, I realized that, in fact, I have SO MUCH to say. I was writing so much that I would have to break it up into multiple articles for each topic. Now I know the issue isn’t having things to say, it’s having the time to write it all!
What’s the best practical or tactical tip you have for a DIY business owner?
CA: When I think about marketing and sales, instead of feeling like a gross, shameless self-promoter, I think about sharing an invitation to a party I’m having. Nobody is going to come to a party you don’t invite them to. So you have to share the invitation.
VS: Everyone has their own unique way of working and internal schedules for when they perform the best. I love creating–once there’s something that sparks my creative goddess I’m full speed ahead, can’t stop me. Taking time off and regular breaks has always been a challenge, but it’s necessary for my creativity and nervous system. A big discovery for me this year were some tools that help me understand myself better so that I can create my own schedule and optimize my time in my own way. Some of the tools I now cherish wholeheartedly: The Kolbe System, The Power Of When, Human Design and Astrology (for my woo friends out there!)
JW: Oh so many nuggets I would give out. But most recently I’ve seen a rise in passive income ideas. I’d like to say that creating a course is great passive income, but it’s anything but passive. Sure the content is written but to sell the thing, it’s a lot of work.
KH: If you are neurodiverse or a Motivational Rebel or otherwise just have trouble sitting down and getting stuff done, try this. Instead of trying to focus on a bunch of tasks for a single project, break your to-do list up (among all your projects) into a grid by the amount of focus needed and the amount of time needed. Here are the categories: Amount of Focus: Can do while multitasking, Average focus, and Deep focus. Amount of time: 30 min or less, 1-3 hours, more than a few hours. Don’t try to get more detailed than that. Then put all of your tasks into the grid and choose what to work on based on your available time and focus level. Things in the “Can do while multitasking” category are great for light research, stuff you can do in front of the TV in the evenings, etc. For tasks with big time + big focus needed, book “cave time” in your schedule (or even better, schedule a co-working time with a colleague.)
Which business tool or software is really rocking your boat right now and why?
CA: I love WaveApps. Is it weird to say I love my accounting software? Because I do. I really, really do.
VS: I use *so* many tools but one particular one that I absolutely love is Canva! (Sorry Adobe, I love you too!) Canva is fantastic because not only it’s so easy to use but the Canva team regularly updates its product with more capabilities. It’s becoming a powerful tool! The background eraser, the brand kit and the ability to import any Adobe Illustrator files are some of my favorite things!
JW: Imagen AI. It’s artificial intelligence for editing photos. It learns your style by reviewing at least 5000 photos. I’ve been using it now on nearly all my sessions and it’s literally saved me hours.
KH: How can I choose one? I love business tools! I’ll limit myself to two. First is Spoke, a transcription software that will automatically record your meetings and provide a transcript! This is SO handy for people like me with faulty memory! I’m constantly going back to transcripts of meetings to remind myself of details for client work. It’s also great for creating training videos, automating blogs from video content, etc. Notion because I am ALL about customization and this tool lets me visualize, organize, and customize all my ideas, processes, goals, etc. I’ve still got a LOT to learn about it, but I could spend all of my time in there if I didn’t have other work to do! I mostly use it for documentation, content, journaling, goal-setting, etc. I’m not 100% sold on it for task management (I love ClickUp for that).
If you could go back and fix one mistake you made early on as a new business owner, what would it be?
CA: That’s a hard one—it’s all been a process of learning. So even the things that I got wrong (like working with clients I wouldn’t work with now) was part of getting to where I am today.
VS: Not having partnered with you sooner!! I absolutely love our partnership and each client we help. Wish I knew you even sooner! Love you!
[Readers’ Note: I did not pay Verô to write such kind things about our partnership, but hey, I’ll take the love all day long! Filing this into my WINS folder.]
JW: Oooo another good one! So many thoughts here. But one mistake that I would fix early on knowing more about marketing.
KH: Oof that is really tough! I think even some of the decisions which weren’t great decisions still had gigantic benefits from them. For example, I spent a huge amount of money on a coaching program that, in retrospect, probably wasn’t a great fit for what I needed. But I can’t say that I would go back and change it because I made some incredible relationships there that were both good for my business (and for me, personally). Similarly, I could say that getting my OBM certification was “a mistake” because I decided very shortly after that that being an OBM was not the day-to-day job that I wanted. But going through the program was still beneficial because without it I wouldn’t have had the confidence to say that I really understand online business and can help a variety of business owners streamline, systematize, etc.
What’s the best discovery or realization you’ve had since being in business for yourself?
CA: I trust myself to create my own opportunities.
VS: How brainwashed we all are about the traditional way of doing business. You’ll often hear common things like “be consistent and show up on social media”, “you need XYZ to have a X-figure business”, etc. The truth is, however you decide to do it is the right way for you. Stop following the “guru” advices and put some time into discovering what business, branding, marketing, etc. means for you and why.
JW: That once I had the volume of bookings, how valuable outsourcing and systems can be to keep you afloat.
KH: That I have a toolbox full of tools that I can use to help people. My multi-passionate nature means that I’ve learned about many different industries and done many different jobs. Each of those is just a new tool that goes into my toolbox and I don’t have to limit myself to just using one type of tool every day! They all come in handy for different situations.
Be sure to check out Part I of the Solopreneur Series: Secrets Of A Successful Online Business.
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