How to Think About Giving up Your Day Job for an Online Business

In today’s lesson I want to tell you a story – a story of advice I was given when I was starting out that I ignored – a story of regret and a story that I hope might move you to taking some action!

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Hi there, its Darren from Problogger and welcome to Episode 175 of Problogger podcast. As I said, my name is Darren Rowse and I’m the blogger behind; a blog, a podcast that you’re listening to now, an event, a job board, and series of ebooks all designed to help you as a blogger to grow your audience. And if you haven’t started a blog, to start a blog too and to make money from that blog. You can find out more about problogger at

In today’s lesson, I want to tell you a story. It’s a story of advice that I was given when I was just starting out, advice that it turns out I completely ignored. It’s a story of regret and a story that I hope might move you into taking some more action in your blog and your business.

Have you ever been given the advice don’t give up your day job? Back in 2004, I was given that advice numerous times, quite a few in fact. I’ve been blogging for about a year and a half and I just discovered that you could make money from blogging. Now, by no means was it much money. I was only making a few dollars a day at first but I was beginning to see the possibilities of monetizing blogs. The dream of going full time as a blogger had begun to grow in my mind.

At first, I didn’t tell anyone about this dream of going full time with my blogging but as my income begin to grow, I couldn’t help myself. I began to tell a few friends and family members about these dreams. Whilst most of my friends and family were very encouraging, or at least they humored me without saying anything negative, I did get that advice quite a few times when I would tell them that one day I might become a full time blogger. Their advice was “don’t give up your day job.”

Often, those words were said in a gentle, joking tone. It was kind of almost like a “don’t give up you day job.” It’s kind of a funny saying people would say. But sometimes, they were actually telling me not to give up my day job and their advice was well meaning. And in some ways, it was wise advice too because who had ever heard of a full time blogger back in 2004? Most of my friends didn’t even know what a blog was, let alone know of anyone who was a full time blogger. There was some wisdom in their advice and it was well intentioned.

I didn’t take it to heart and I certainly didn’t let those words have much of an impact upon me because basically over the coming years, I did begin to give up my day job. I would say actually it was day jobs because at that time, I was working a number of part time jobs. I was working as a youth worker and a minister in a church. I was working in a factory packing parcels, I was working in an catering kitchen putting food on trays, I was working as a casual laborer doing things like assembling Cirque De Soleil tents. I only did that one day, it was too hard for me. I was also studying part time. I had the luxury of having lots of different jobs that I was working.

Gradually over the coming year or so, I began to give up those day jobs. It was a gradual process, it certainly didn’t happen overnight and it took me a year or so to really give them all up to the point where I was a full time blogger. I will link in today’s show notes to the full story if you are interested in reading that.

Over that time, I did begin to give up those day jobs. The before and after shots of my life from 2003, 2004 to now in 2017, they’re quite remarkably different. My life is very different today because of blogging. I’m so glad I didn’t listen to that well-intentioned advice of my friends not to give up my day job.

A year or two ago, I caught up with a friend who’s a long term friend. And this friend reminded me that he was one of these people who used to say to me, “Don’t give up your day job,” way back in 2004. I don’t remember this friend actually ever saying those words to me but a year or so ago, we caught up for a coffee and he kind of confessed to me that he’d said those words. He had been feeling guilty about it because he had been thinking about it ever since. He worried that perhaps I had been harboring some kind of resentment to him for telling me not to give up my day job. He was quite relieved to know that I didn’t even remember him saying that.

But one of the things that interested me in that conversation with my friend is that he also told me that he regularly wondered what would have happened if instead of saying, “Don’t give up the day job,” he’d actually said, “How could I do it too?” My friend is quite similar to me. He’s got lots of interest, he’s a good communicator, he’s a gatherer of ideas, he’s researcher and he’s got on entrepreneurial kind of spirit within him. He thinks about things in an entrepreneurial way.

He told me as we caught up for this coffee that when he saw me starting my first blogs back in 2002, 2003, 2004, that part of him wanted to do the same thing. He thought it would be fun, he thought it might have opened some doors of opportunity for him. But he also had these others voices going through his mind at the same time. The voices that said things like all the topics are being taken, everyone else has already started all the blogs. What if it doesn’t work? What if it’s a waste of time? I’m too late. What if I look stupid? There were little excuses running through his mind, little bits of fear, little worries that he had.

Instead of saying, “How can I do it too?” He said, “Don’t give up your day job.” He told me that he regretted that for 10 years. Now as he told me that, there was this pause in our conversation. We both reflected upon the decade that had gone by ever since and how things have played out for both of us. By no means had his life turned out badly. He’s got a great family, he’s had success in the employment that he’s had over those 10 years. On the other side of things, neither has my life been a complete fairytale; building your own business is tough.

But there was a real sense of regret in his demeanor. In the conversation, he then went on to tell  me that he wished he hadn’t missed the boat of getting into blogging and that for the last ten years, he’d still wondered if he should still start a blog, or a podcast, or Youtube Channel. He in the last few years had even brainstormed topics that he could start a blog on. He bought a domain, he planned out content ideas, he even bought my book, The Problogger Book without telling me a few years ago.

The thing that continued to hold him back is that when he looked at what was happening on the web today and how it developed, he kept saying to himself it’s too late to start, it’s too late to build anything that could be substantial today. He had this feeling that everyone else had all the topics already.

It was that moment in our conversation that I just felt like jumping up from the table and shaking him because I had those same feelings back in 2002, 2003. I remember back when I first started my first blogs and started to monetize them that I looked those little blogs that I had and I started to compare them to all the other bloggers who’d already been at it for two or three years.

I remember when I first started my first photography blog looking around the web thinking there’s already hundreds of other photography sites out there, how could I ever build anything of significance. I looked at the following that others have built, the influence that they have, the skills that they have accumulated and I distinctly remember thinking to myself I’m too light.

I suspect most people, most bloggers have felt that same thing at one point or another. And you listening to this right now probably had those feelings and maybe have them right now. We all tend to compare ourselves to others further along on the journey. Many of us have these feelings of inadequacy when we do have those moments of comparison. It’s completely natural to have those feelings but it’s such a shame to let them overwhelm you to the point of paralysis like my friend.

I don’t think it’s too late today. If anything, this revolution that’s happening around us on the internet at the moment, is only just the beginning. We’re in the early days of this. Sure, there are so many people engaging and creating content on the web, but with that comes opportunity. Alongside that, we see an expanded audience. There are still parts of the world that are coming online today. Our audience has the potential of growing.

As one of my favorite social media practitioners Gary Vaynerchuk put in his book the Thank You Economy, he says, “There’s a gold rush happening, where are you?” Gary said that back in 2008 in his book, but I still think it’s a completely relevant message today.

I wanna be really clear here. I’m not saying you should quit your day job today. That would not be responsible in particular if you haven’t started blogging yet or if you are in the early days of your blog. But if that’s a dream for you, there are things you can do today about it. The key is to do something today, the key is to start today if you haven’t started. The key is to get over the fact that you’re not the first and to start creating something that matters today. The key is to get the ideas that swim around in your mind out of your mind and to take some action on them, today. The key is to start developing your voice and putting your ideas out there today. The key is to start building your network and an audience, today.

The key is to start developing skills that you need for this, today. The key is to move past your fear of not being good enough or not having the skills and to take you first small steps today. The key is to do something today.

Thanks for listening. Over the next few weeks, we will be starting a series on Problogger about how to start a blog but you can start today. You don’t need to wait for that series, but we will be providing you with some further content to help you on that journey.

In today’s show notes, I’m going to link back to that story of me starting my blog and the progression of giving up some of those day jobs but I’m also going to link to an article I wrote last year on how to start a blog.

If this is something you’ve been putting off, I really would encourage you to go and read that particular article today and to register that domain, to begin to brainstorm topics, begin to put that blog together today.

I look forward to seeing what happens as a result of that journey today.

You can find today’s shownotes over at Do something today.

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