The Realities (and Reflections!) of a First-Time Startup

Stories of a Startup

This post takes a very candid look at what I consider to be the big lessons I have learned on this startup journey of mine (it’s been 8 months or 3 years – depending on the perspective you take). It will reflect on observations made in the running of my own business as well as in supporting an amazing group of coaches as they run theirs. And let me tell you – these coaches are all at different stages in their respective entrepreneurial journeys, and they serve different niches. So there is plenty of learning happening here.

What I will not go into is things like “Go in with a plan”, “Define your target” or “Aim to wow your clients every single time.” In my mind, those are a given of doing good business.

Instead, these are my more personal takeaways in no particular order:


1. Find your biz wingman (or in my case, women!)

I spent 18 years in the corporate world and right the way through, I was blessed with the luxury of seeking out coaches and mentors. I valued the ability to bounce ideas off someone who’d been there and done that. I valued hearing an alternate perspective from someone I looked up to. I valued the discomfort of constantly being pushed outside my comfort zone. I had the benefit of being around people and learning by osmosis.

Building and running an online business is fundamentally different though. It can be isolating and doesn’t necessarily offer the same level of support. And yet, it didn’t occur to me to reach out. How ridiculous is that?!

Anyway, fast forward a few months and I am now part of an amazing business coaching group that challenges me, teaches me and meets me where I am as a new business owner. Best decision ever.


2. Just. Start.

Holy moly. This one was a big one for me. I spent so much time thinking I wasn’t quite ready to put myself out there, to offer my services to “real” clients and it felt like I was on this learning loop that went on and on. First, it was the digital marketing certification, then it was Infusionsoft training, 10 bajillion webinars/websites/e-books, and work-for-free internships. I finally hit a point where it just didn’t make sense. (Plus, I read somewhere that if you’re not earning an income on it, it’s really just a hobby. Big sigh.)

So, I psyched myself up, told myself to “suck it up, buttercup” and put myself out there. Pitch after pitch. Drawing on what I knew. Fine tuning my process, my proposition and my message.

Landing that first client? No words to describe how I felt.

I’m reading Russell Brunson’s “Expert Secrets” at the moment and very early into the book he says, “You don’t have to be the most knowledgeable person in the world on your topic, you just have to be one chapter ahead of the people you’re helping.”

That right there is exactly the belief I needed to embrace then, and still embrace now.


3. Bootstrap it every way you can

It’s incredible the number of tools, tech, courses and resources available to online business owners. It can be so easy to get carried away. For me though, the fact was – we, as a family of four, had just traveled 13,000+ kilometers to live in and explore a new country. The time, money and energy that took was colossal. So I knew that I had to get clear about my priorities, and what I actually needed to invest in to be able to deliver on those priorities. It was all need vs. want.

Thankfully, in the online business support space, the list is actually quite small (and it’s amazing the quality you can access at little to no cost- without compromising professionalism.)

  • A laptop and internet access
  • A well-hosted and well-designed website (even a one-pager will do!)
  • A scheduling tool
  • An email service provider
  • A project management tool
  • A means of talking to clients
  • An invoicing mechanism

That’s all I needed to find job opportunities, write proposals, put myself out there, connect with clients, deliver on my promise, and get paid. So that’s all I had.


4. Know your numbers

This one is pretty straightforward but I didn’t get to it until a few months in. Silly really, considering I have a background in banking. The thing is, you cannot possibly manage what you cannot see and I’ve learned that you really have to know how much you have going into your business… how much you’re spending and making… and where your “It’s time for plan B” point is.

So I started two separate Excel sheets. The first tells me exactly how much I am going to earn based on the projects and client load I have on at the time. I like having a 3-month projection at the very least so that I am able to plan my marketing efforts to close any gaps when necessary. The second sheet lists all my expenses, categorized with tax time in mind and set out on monthly tabs that roll up to a formula-driven consolidation for the year.

An awesome side effect I saw coming out of this process was the buzz I got from actually seeing my month-on-month growth numbers, plus – when I did decide to invest in the biz, I could do so with a clear conscience.


5. Done is better than perfect

This is a hard lesson that I’m still learning. One of my clients is truly amazing at what she does and I have mad respect for what she achieves on a daily basis. It always boggles my mind how she’s able to manage a thriving business, run a successful podcast, blog and YouTube channel, create several online courses, and coach people transitioning from a 9-to-5 to freelance setup. And by the way, there’s a personal life that goes with all of that too.


What would take me a long, long time to put out there, I’ve seen her turnaround very quickly. And sure, her experience is something that she has working in her favor, but what I think matters more is the fact that she just gets on with it. She has an idea, validates it and focuses all her energy on getting it out there. And I love that. If there’s one thing I need to learn – it’s that done is better than perfect… that this entire process is iterative. There comes a point in a project where it’s time to stop tweaking and to put it out there. You can’t sell something if it stays hidden on your hard drive 😅


6. Geek out on all the systems and processes

At the startup phase, there’s always going to be so much to do in so little time. It’s very normal for things like setting up your systems and documenting your processes to fall to the wayside. But if there’s anything I’ve learned, it’s that investing in the setup of my system makes it easier to bring on new team members and set them up for success… it makes it easier to scale my business… and it makes it easier to maintain consistency in my service delivery to clients, regardless of what’s happening around me.

The systems we create become the foundation that supports us and our business as it grows. While it’s taken me a bit of time, I’ve focused my energy on automating and/or standardizing my high use, high impact processes. In addition to a clearly defined file and folder structure for all my records, this also included proposal submissions, client intake, task/project management, content planning and delivery as well as invoicing. For other ideas, here’s another post I wrote recently on the issue of systems. (Refer: 5 Solutions to Destress Your Business Right Now)


7. Stay in your lane

This one is about playing to your core strengths. Three years ago, the seed of a dream took root. A dream to be able to start my own location independent thing… to earn the freedom to work on what I want, with whom I want, when I want so that I could have more of me left over for my gorgeous family. Here’s the thing though – when I first got started, I went down the generalist VA route. I took on clients who wanted me to assist with tasks that neither played to my strengths nor offered me any development opportunity. I pitched for jobs outside of the industries I knew. Long story short? I found myself in “pivot or persevere?” mode.

But after several conversations with myself and those closest to me, I found my center again. I got clear about who I wanted to work with, in what capacity. I got clear about the types of tasks and projects that tapped into my zone of genius. Over time, I renegotiated my client and project portfolio. And most importantly, I honored those choices- even if doing so meant referring a potential client on to someone else in the VA/OBM world.


8. Your “wheelhouse” will grow, constantly

One of the greatest gifts of this journey, for me, is the ability to say “What I know right now will take me 90% of the way with this particular project…. but that’s okay cos’ I sure as hell can learn the rest.”

And guess what? Learning that last 10% has never been easier. Blogs, forums, skills-specific Facebook groups, webinars, 30-day challenges, virtual summits, online courses – I’ve only ever had to decide which worked best for me > find it > learn it > find someone to practice on > offer it as a new service.

Of course, I’ve also had to learn that not all learning is equal. I have to see a clear line of sight between the learning and the longer term goals I have for myself and my biz. As much as learning to write code would be so much fun, it’s not going to help me in the long run.


9. Know your ‘why’ and lve what you do

What a cliche. But it is so true.

You absolutely have to love what you do because when things get tough, and they will sometimes, it’s the passion you have for what you do and who you help that continues to fuel you. I’m not entirely sure what my expectations were going into this journey but man oh man, I underestimated the obsession, drive and discipline it takes to do well (Hey hey, waking up at 4:30 every morning, just so I can spend a few hours focused on my own business before getting to client projects!)

This working for myself thing is several layers of self-doubt, validation, anxiety, and victories. But I am crystal clear about who I want to work with (those who help others become the best versions of themselves) and why. For as long as my business decisions align with that, I can keep going.


Writing this post, I can’t help but wonder what the picture will look like for my business 12 months from now. I suppose we’ll just have to see!