Technology / Business websites

5 reasons running an online business is harder than I thought

So you’ve made the lifestyle choice to start running an online business. It will give you more time with your kids/to travel and better control over your own destiny - right? Well ...

23 February 2016 by

Seven years ago, after 16 years of working 60+ hour weeks in the corporate world, I took the leap. I started running an online legal business.

Everyone said I was crazy: friends, colleagues, family. Why would I leave a great and reliable salary, my respected title and position … and why would I do it when I loved my job?

Well, I was craving autonomy. And the flexibility to work the hours and times I wanted. I was a hard worker with a great idea. How hard could it be running an online business?

The answer is: harder than I thought.

"Running an online business tests you in so many ways: your self-discipline, communication skills, focus, ability to manage pressure …"

1. You are expected to be available 24/7

If you’re running an online business, customers expect you (or someone related to the business) to be available 24/7. They will call, they will demand, they want service NOW!

I receive calls at all hours of the day and night. And weekends. Sometimes it’s for legal advice, sometimes it’s for a template purchase confirmation that’s gone missing (usually into their spam folder) and sometimes they want validation of their business idea. Now!

Unfortunately you cannot screen the telephone calls (because of those times something is genuinely urgent). But you never know whether something is genuinely urgent until you’ve already answered!

2. Customer expectations can be a little … unreasonable

With the growth of the internet, customers expect the best product or service at the cheapest price, delivered yesterday.

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Sometimes a customer has a slower internet so there is a slight delay for receipt of their email products. Sometimes they put in the wrong address details so their products do not reach them. Once a customer even put in his wife’s email details and phoned to yell at us for the fact that he did not know her password. (While he was on the phone, the templates came through and he hung up. Mid-sentence!)

3. Customer emails can be … mean

If a customer walks in a bricks and mortar store, they’re more likely to make an effort to be personable and give you the chance to build some rapport. But it’s easy to be curt in an email. I’ve lost count of the number of people who’ve taken their bad days out on us, simply because they know they will never meet us!

4. No ‘Out to Lunch’ sign for you!

There is no such thing as a ‘lunch hour’ for you as an online business owner. In fact, this might be your busiest time of the day: when many of your customers are on their lunch break!

5. There are still many regulations to contend with

Both bricks and mortar and online business have to comply with regulations – it is not necessarily easier with an online business. For bricks and mortar businesses, you need ‘slip n fall’ insurance in case someone falls in your store. For online businesses, you need to comply with privacy laws for the details your shopping cart collects from your customers for your purchase. You don’t have to hand a privacy policy to physical shop customers but you do for online shoppers!

Yup, running an online business tests you in so many ways: your self-discipline, communication skills, focus, ability to manage pressure …

So why do I bother running an online business?

The list above may make you think running an online business is not worth the hassle. But I have experienced, and continue to experience some great benefits:

  • Once I decided to jump in ‘feet first’ it was easy to get started with little cost involved (‘sweat equity’ more than anything).
  • I’ve met amazing people I’d have not come across otherwise! Some of them have some fantastic business startup ideas and I am proud to feel part of their now growing businesses.
  • I can work from anywhere in the world (and in PJs if I want!).
  • There is unlimited income potential.
  • I have, and continue to build, a valuable asset

So for all that it’s been harder than I thought, I have no regrets. I have a successful business, a great team to work with and love LOVE my job. I wake up excited every single day to see what’s next, what new customers I’ve attracted and energised to implement new ideas.

If you’re considering starting an online business my advice is this: do your research, prepare … and then JUMP IN with both feet! (And enjoy the ride because while it will be wild, it will also be super-exciting!)

Are you running an online business? Do you feel the rewards easily outweigh the challenges?

Vanessa Emilio

is a Practice Director, Lawyer, Founder and CEO of, a legal website business with easy-to-use, inexpensive legal templates, forms and agreements for everyday Australians as well as lots of useful information.


  • Yeah, I too thought that it’d be easier. I thought I saw it all during my IT contracting years, but things that weren’t accounted for just keep on popping up. The fact that our mission is to make the life of other small businesses easier is a funny paradox 🙂

    • And I bet continued to ‘crop up’-it seems never ending to have online businesses where new issues arise! I am in awe of IT and website developers who are adept at managing their clients well when we see some of the issues that arise……:)

  • Hi Vanessa. Your title “5 reasons running an online business is harder than I thought” resonates strongly with me having started an online insurance brokerage specialising in business insurance 3 years ago. While many sole traders and small business owners are complimentary to our brokers I relate to your comments that the tone of many conversations are very different to traditional face to face conversations. I love your business concept, the templates seem very relevant to us and that you DO take calls too. I’ll purchase some templates very soon and promise to be especially nice and patient if I need to call. Mark Vanzo.

    • Hi Mark-thank you for your input and agree-especially with insurance, it can be tricky and is a learning experience to deal with customers via email alone. Some online businesses do not require any input from customers for their goods or services but if you have businesses like ours, it can become an artform to ensure you ask the right questions! Love to speak anytime and best wishes for your great business model!

  • J21

    I too thought it might be easier. But because it’s my own business (rather than working for someone else), I celebrate personal triumphs and feel setbacks harder.

    • I agree! And I thought it would be faster to set up and manage. So wrong I was!! Hope it is going well for you J21.

  • Interesting that this article pops into my inbox today after yesterday google have AGAIN changed the goal posts on my business by removing the paid search on the right hand side. I have had an eCommerce site for over 15 years, it has been an interesting ride and to see the changes over that period in not only the customers expectations but the SEO changes (this was not a thing when we first started) have been incredible… I guess on reflection, I had no idea how difficult it would be as it was so new then that most of the issues that I face everyday now were not invented yet! I do think if I had to give one piece of advice it would be to have a very strong customer service policy that all the staff have access to and know inside out.

    • So right Kerry! It seems one of the biggest issues online businesses face is the constant changes required: to websites, to updates (legal, SEO, advertising etc) and also to Google algorithms which seem to happen on a regular basis. It is very difficult for business owners to keep up. I also agree on clear terms for customers-it is one of the most fundamental aspects of your company and business to ensure longevity and transparency. Hats off to you for having an online business for 15 years!!! You were and continue to be one of the long time success stories-Congratulations!

      • Thanks Vanessa, sorry was in the middle of moving house so have just logged on… Happy Birthday to me today! 🙂

    • Hi Kerry. Yes Google are always tweaking something. This week my credit card provider (who I use to pay for Google Ads) changed their policy and charged me a large international transaction fee for Google Ad purchases. This is because as you know Google Ads is based in Singapore and thus it’s an international payment (despite Google having a large office in Sydney!). Bang goes my Emirates miles. I’ve had to change to another credit card provider! Ah the joys of Google.

  • Hi Vanessa and thanks for this article. Having been one of your customers recently I have to say I have been extremely impressed with your immediate responsiveness, to your point #1 Be available 24/7. And I was amused when looking at the emails in my inbox just now. Right below the Flying Solo with your “5 reasons…” was “Start your on-line business in 5 minutes”
    and BTW: thanks for all your assistance with my legal matter!

    • Hi Ingrid, I totally agree. Vanessa’s customer service and responsiveness is out of this world. Vanessa, having an online business can definitely be hard, but I’m so glad you jumped in with both feet! 🙂

      • (Blushing-but happy!!) Thank you Lucinda-think I can honestly say the same for your business, having been a customer of your business! It is nice to hear that others feel the same who have been the long time business owners-particularly with the 24/7 comment-glad it is not just me!

    • Our pleasure Ingrid and thank you for your lovely comments. It is quite ironic to see the number of articles that are “I started 5 online businesses in one week/5 minutes/5 days”!! It makes one wonder about the longevity of these businesses……:)

  • Excellent article. I really connected with it. Thanks very much.

    • Thank you Alexandra. Its nice to know I am not the only one feeling this-confirmation appreciated!

  • Hi Vanessa, a really great article. And so true. I would certainly say in relation to Ergoflex and myself that rewards outweigh challenges. And there are a few challenges. #6 customer reviews….can make or break you or drive you crazy!

    • Thank you Matthew. And Customer reviews can also be great feedback to be able to improve and understand your customers better. I very much agree, the rewards definitely outweigh the challenges….which continue always with an online business!

  • DecaffeinatedBoy

    Yes excellent article Vanessa, I’m new here but very glad I have found this site. Being a solo worker on my Online Store I can certainly relate to the article. The worst part of the business for me is the 24/7 aspect along with the “no Out to Lunch”. Actually taking a holiday (or not being able to) is by far the hardest/worst part and something that I wasn’t prepared for. My partner gets angry at me when we go away and I am checking my phone for orders and problems. Kris

    • Hi DecaffeinatedBoy, I agree-out of all the points, that is, was, and continues to be an issue for me (the constant and necessity to phone check, available 24/7). I have found that eventually my partner understands and appreciates how important my business is to me and even more so, appreciates seeing me more often as a result of not being away all day in the city office. But importantly (and sage advice!) I have found also that sometimes you just need to put the “Out to Lunch” up to save your sanity:)

  • Wow Vanessa, You nailed it. I also run technology business and stop it in a year. But still planning to re-launch again. Thank you for excellent wrap up 🙂

  • Excellent article Vanessa, it’s always refreshing (in a way) to read an article that tells the other side instead of just the “rainbows and unicorns” perception.
    There are upsides and downsides to every part of life, choosing what works for you is the key to happiness.
    Thanks for sharing.

  • Such motivational ideas you have shared in this post. I really enjoyed this stuff and would love to share it in my personal groups.

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