12 lessons from quitting the day job and starting a business

Late last year, Craig Barber quit his job as a designer to be a full-time entrepreneur. He gave himself 3 months runway to build, launch and get paid by Logobly, his logo maker startup.Craig Barber quit job lessons

Craig had dabbled in side projects before. But had never changed careers to focus solely on a startup. This was it. No safety nets and no other income.

It’s been just over 30 days since Craig made the change and we’re sharing his learnings so far with the Escape community.

1. Have a plan

You have to have a plan. My plan is pretty simple. I’ve got 3 months to do the following. Get people to sign up for my logo maker. Design, build and test the logo maker. Launch the logo maker. Get paid. That’s it. It’s not complex. But there are a lot of moving parts within this plan. You must have a basic plan set out before you begin. It also helps to have an exit strategy. If my plan fails, I can always go back to being a designer again.

2. No one cares or understands what the fuck you’re doing

Unless you’re deeply submerged in the entrepreneur and startup world, no one really understands or cares what you’re doing. I first told everyone I was an Internet Entrepreneur. Yes, I know it sounds a little dicky. But I still like the term and technically that’s what I do. But then I’ve started to revert to ‘I’m building a business online’. I also back that up with, ‘I’m creating a logo maker’.

3. Avoid negative people at all costs

It’s hard enough to be your own cheerleader every day. It’s even harder when you’ve got people around you that doubt and don’t believe what you’re doing. Sadly it’s always the people that are not happy with their own career that often start dumping on your plans. It can be really tough to be around these people. So try to avoid them. If they are your close friends and family, avoid talking about business or work and what you’re up to.

4. You must have a routine

Being your own boss is sweet. You get to keep your own hours. But I’ve found I pretty much stick to the same routine every day. Wake up early, go to the gym. Work till 5.30. Repeat. It keeps you in check. I think if I had no daily routine I would quickly find myself just fucking about, going to movies, eating badly and maybe spending too much time with friends when I should be working.

5. Have a dedicated workspace

Your environment really matters. Unless you’ve got a dedicated office space at home. I would avoid working from home. I specifically hired a co-working space for 3 months. I know this would keep me honest and putting in the hours every day as I’m paying for the space. If you can’t afford a co-working space, find a library or other dedicated space.

6. You have to be really, really self-motivated

When you’re working for someone else, you’ve got deadlines and meetings and presentations. When it’s just a company of one, you really have to be cracking the whip for yourself. Money is, of course, a key motivator. That panic that your business won’t work and you won’t be able to pay rent is a nice vivid reminder to not fuck about.

7It’s fucking lonely

It is lonely. I purposely joined a co-working space to try to counter this as I knew it would be a challenge. The co-working space is somewhat social. But it’s not like working in an office environment. As a solo founder you’re a company of one. I’ve found I really have to put in an effort to socialise with folks in the co-working space. It does not come easy as everyone is doing their own thing. I also have to plan regular catch ups with mates during the week to balance it out. It’s another reason why most solo founders are so active on social media. They need that daily banter. Be ready for this if you’re making the leap.

8. Always be selling

Being from a creative background it’s a challenge having to sell my business all the time. But I’m getting better at it. I figure if I can find creative ways to sell my business, it’s less sleazy and salesy. I do still find it a challenge as I always feel like I’m asking something of people. Please like my tweet. Please sign up on my landing page. Please read my blog post. It’s a non-stop challenge and you have to sell yourself and your company.

9. Be nice to your community, you need them

As far as leverage goes, you’ve only got so much. In order to amplify whatever you’re doing, you need the power of your community. Mine is Twitter, LinkedIn and email. There has been a number of times the community has got behind something I’ve done and it’s really helped me. At the same time, I make an effort to help others when I can.

10. Everyone tells you what to do, no one does it

So many people have advice on how to run my business or what I should be doing. Whilst I like to talk about my business with folks and listen to what they say. Most of the people giving advice have never done or are doing what I’m doing so it’s hard to take their advice.

11. Commuting is evil

I no longer commute and my life is so much better for it. Now, when I get on the train I often start to stress the fuck out. Spending two hours of your day, 14 hours per week commuting is just nuts. Try to avoid it if you can as it’s really a waste of time.

12. It’s a healthier lifestyle

I’m actually healthier now than when I had a full time job. Everything you read about this hectic 24/7 entrepreneur lifestyle doing all nighters and eating takeaway and guzzling coffee may be true in some circles. But not mine. I’ve got time to go to the gym every day. I’m not stressing the fuck out over work. I’ve got control of my life and that’s what it’s about. It’s amazing how much more chill you get when you’re in control and not on the clock all day.


All in all, I’m really enjoying ‘the life’ so far and I want to continue. If you liked reading this, check out my new startup Logobly and connect with me on LinkedIn. Helping me spread the word will allow me to continue doing what I love and means I won’t have to go back to work and get a real job : )

If these escape tips from Craig have inspired you to make a career change:

escape the city logo

Share This