So where do I start? I figure if the title of this article caught your attention, perhaps you are expecting to hear the perks and the flexibility of being an online entrepreneur. The truth is I have been struggling with what to write here for a number of weeks. Not because I was uncertain of the topics to be covered, but more so, about how do I create a realistic but not too frightening picture of online entrepreneurship. Yes, I said ‘frightening’ - cue the creepy music. 

I grappled with the anxiety of not wanting to lead you, dear reader, astray as I contemplated the literary fluff I could apply to the topic at hand. The leisure, the flexibility, the freedom of being able to work anywhere and manage a team who all work remotely and in the comfort of their own homes. But it’s not all pretty or fun and terms like ‘Digital Nomad’ coined for people like me who can work from anywhere in the world are great, but maintaining this lifestyle is hard.

The ‘reality’ that exists online created by beauty and travel bloggers, life coaches and celebrities is that this life of leisure is an illusion. The truth is, it takes a lot of work and the sacrifices can include but are not limited to: sleep, time away from family, money, friendships and even your privacy. However, dear reader, the juice can be absolutely worth the squeeze, so fear not. A Day in the Life of an Online Entrepreneur can depend on anything from: the alignment of the stars, phases of the moon, your team members’ wellbeing, client satisfaction (or lack thereof) in addition to a plethora of other possibilities, but a couple of key truths usually remain the same – it’s absolutely fulfilling and WiFi is necessary for survival of course!

So here are a few facts about a regular day for me, give or take a few and in no particular order.


Depending on the type of person you are, this can be easier said than done, but when you are managing yourself and a team, you really don’t have a choice but to develop a routine and stick to it. On a good day, I wake up with coffee (the elixir of life – next to wine that is) and I practice gratitude. I list each morning what I am grateful for and remind myself of my goals through prayer. Then I do about 15 - 20mins of meditation to get my head straight, outline my main objectives for the day, followed by a shower etc. Then all hell breaks loose when the kids wake up. This little morning ritual is what really focuses me and gets me motivated. I have a home office so apart from school drop off or early meetings I am not commuting to an office.


Yes, yes, yes I admit I have worked in pyjamas before (usually on weekends) but here is one of those illusions I am determined to ruin for you. Working from home or remotely doesn’t mean we are lounging on a couch with daytime TV on in the background (it does happen – but not too often). I dress for work each day, having a home office doesn’t excuse me from being professional. I do get away with flip flops and changing my pants in the middle of the day to yoga pants if necessary, but dressing for work at the start of the day gets me into the right mindset, which is particularly necessary when I am holding myself accountable for work which MUST be done.


Some days are easier than others in motivating myself, but there are days when I have several low points; many entrepreneurs can empathize with this. We question our decisions, direction, intentions, beat ourselves up a bit, drink some more coffee and keep going. It’s so easy to lose focus or compare our journey to someone else’s; success is subjective – every time you make that decision to scrape your head off the desk which you have likely banged your forehead on repeatedly is a success to be celebrated. So, I put on blinders and I get tunnel vision about my tasks and I keep going.


Here’s one of the major perks of online entrepreneurship (yeah, I know you were worried that I was just gonna depress the hell out of you) – I’m at home! My family respects my space, so they treat it (almost) like a sanctuary for my work – I also have a do not disturb sign that I hang up on the door which deters a 5-year-old from busting in to play Legos or a teenager coming in to ask me about snacks, but for the most part my door is open. However, few things top being able to stop what I’m doing to go outside for a walk, play 123 Red Light with my son, have lunch with the family or a pow-wow with the hubby in the middle of the workday.


Well almost…

Working online and with a business that focuses on Digital Marketing, means I am literally almost always online. I am researching constantly, reading blogs and relevant articles, widening my network strategically, following feeds and individuals for insights into a strategy for my company and my clients. This comes at a great disadvantage of having to force myself to unplug. During a recent family trip overseas, I worked every day of my so-called ‘vacation’. On the days I slept in, I was up late the night before with a client or working on strategy. On the nights we went out, I would wake up early that morning to send off invoices or work on projects. Running a business never stops, the bitter-sweet element of your business being online means you can never escape that fact.

So here we are towards the end of my workday. Despite the hard truths and what may sound like complaints – I wouldn’t change a  thing. The daily life of an entrepreneur sure has its up and downs, but towards the end of each day, I look at my massive to-do list which always gets longer, and a sense of pride and cautious excitement fills me; that this is all mine. 

Contributed by: Anika Repole Wilson