February 7, 2020

It’s Been 30 Days Since I Quit My Job To Be An Entrepreneur, Here’s What I’ve Learned

Craig Barber @CraigBarber

Late last year I quit my job as a designer to be a full time entrepreneur. I’ve given myself 3 months runway to build, launch and get paid by logobly.com, my logo maker startup.

I’ve dabbled in side projects before. But I’ve never changed careers to focus solely on a startup. This is it. No safety nets and no other income.

It’s been just over 30 days since I made the change so I thought I’d share my learnings with you so far.

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.

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’.

Avoid negative people at all costs

It’s hard enough to be your own cheerleader everyday. 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.

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.

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 everyday as I’m paying for the space. If you can’t afford a co working space, find a library or other dedicated space.

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.

It’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.

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.

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.

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.

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.

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 everyday. 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, please share it or hit the like button. 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 : )

  1. 12

    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.

    This is an underrated point. The vast majority of the world's productivity comes from extrinsic motivation. Having a boss or colleagues that you don't want to let down is a powerful enough force to get billions of people to wake up and go to work from 9 to 5. As a founder, you don't have that force at your back, so you need to make up for it intrinsically, i.e. with self motivation.

    You can also do a few tricks to emulate extrinsic motivation, however:

    • Find a co-founder or a partner. Schedule co-working sessions. Report to each other with progress every day. Set up your work so you rely on each other to get things done.
    • Take on advisors or even investors. Just someone who you don't want to let down, and who's incentivized to care about the performance of your journey.
    • Get users ASAP and work in public. In the early days of IH I was a machine, primarily because I knew every Thursday I needed to send my weekly newsletter with progress updates, and I didn't want to show embarrassing little forward progress.
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      Hey Courtland! Thanks for weighing in here : )

      I really love this tip: "Get users ASAP and work in public."

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    It’s hard enough to be your own cheerleader everyday. 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.

    This hits home hard.

    People don't understand what you're doing, and they don't want to. Even your friends, family, and even spouses have a lot of vested interest in not rooting for you to succeed, but it's not like they'd admit it or even are aware of it.

    Friends see themselves as equals to you, and they want you to improve, yes, but not become better than them. There's a lot of subliminal jealousy involved when you're striking out on your own and reminding them of their own failure to take charge of their own lives. Don't expect them to cheer for you all the time. It takes a truly big person to do that.

    Family have their own vested interests as well, especially parents. They want you to opt for something safe and preferably prestigious, so that they can gain bragging rights and also benefit financially from your stable boring career. Don't expect them to support you wholeheartedly.

    Spouses are the same. They want you to stick with the stable source of income. Don't be a hero. She wants to lead a stress-free comfortable life, not worry night and day with you about your nascent business.

    So you're right -- and that's a beautiful phrase -- you have to become your own cheerleader. Nobody is really rooting for you to succeed 100% because they have other priorities for you; your happiness is wayyy down on that list of priorities, that is, if it even makes the bloody list.

    Only you care for you.

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      Man, really well put... it's an ongoing struggle right? That's why people do speak about having a chip on your shoulder and bordering on arrogance. Sometimes it's the only thing carrying you through : )

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      Sadly enough, this is so true.

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    Hi Craig! Thanks for the post. I took a bit longer of a route to making my own product after I left the agency life. I am a graphic designer by trade :D

    I switched to freelance for a few years before going the product route.

    I totally agree with everything you've said. My product also involves making logos haha. You are creating logos, whereas my product Logo Package Express exports logos which have already been created. Your product is for clients, mine is for designers.

    I didn't keep as strict hours as you do when starting off. I always started at the same time, but would often work into the night and on weekends. Most of the time I was only working on my side project for half of the day.

    You must ABSOLUTELY be self-driven. My girlfriend and all of my friends had a vague understanding of what I was doing, but they couldn't really celebrate the victories with me because of the technical ignorance.

    My girlfriend did buy me little snacks and stuff when I launched or had some successes.

    I'd love to chat with you because I think you could actually utilize my product to enhance your offering.

    Congrats on making the switch!

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      I love this:

      "My girlfriend did buy me little snacks and stuff when I launched or had some successes"

      I need a girlfriend like this man! : )

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    Your points really resonate with me, since I'm in a really similar situation as you - I also quit my job very recently and have about 3 months of runway to become profitable with my projects 😂

    Best of luck to you, man!

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      Hey Richard! Thanks for the kind words and good luck to you. Be sure to post your project / startup here : )

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    Thanks for sharing all of this and congrats on making the leap! I'm still part-time and probably won't have the courage to quit until I have enough revenue to support myself.

    As a freelancer though, most of those points really resonated with me. Loneliness is one of the worst - sometimes I feel like I'm actually losing social skills if I don't proactively meet up with friends and work from somewhere other than home.

    When I was reading through, I also thought a good portion of those problems would be a perfect opportunity for a new product to try and solve. (Hint, hint, for any aspiring founders reading this post!)

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      I'm still part-time and probably won't have the courage to quit until I have enough revenue to support myself.

      That isn't courage, that's foolhardiness.

      9 times out of 10, you don't really need to quit your job to bootstrap your side business.

      The benefit of having full control over your time is far overshadowed by the worries of not having income and burning your savings without breakeven point in sight anytime soon.

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        Sure, if your breakeven point isn't in sight anytime soon then you might consider this "foolhardiness" but I don't think someone should necessarily wait for a safe moment to switch to full time.

        If someone, for example, could be breakeven in 3 months after going full-time, would that still be foolish? It's entirely subjective and depends on how realistic those projections can be. If someone never takes a chance to give a project the attention it needs to succeed, then it might never ...succeed.

        Risk tolerance/aversion is a huge factor here. Some people thrive in tough situations and produce results you'd never achieve on just "nights and weekends."

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          Sure. Like you said, if you're reasonably confident that you'll be cash flow even or cash flow positive before your runway dries up, it's perfectly rational and even recommended to quit your job to go at it full-time.

          I've seen way too many who pull the plug too soon, however. I'm a firm "chicken entrepreneur," meaning I don't let go of one branch until I've firmly grasped on to another. It's the logical thing to do.

          And if my idea isn't the kind that I can build and scale part-time, I don't want that idea anyway. Because even after I go "full-time," I still want to do it part-time... The rest of the time I want to be living life. I don't exist to serve my business; my business exists to serve me.

    2. 1

      Thanks Matt, I appreciate the kind words.

      Yes, you gotta keep it social as it can get tough. : )

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    @CraigBarber Congrats to making the leap and kudos in the self-confidence and self-belief. 👍
    You've touched on just about every valid point that any beginning Indie Hacker needs to hear. I wish you the absolute most success possible with Logobly!

    Please continue to share aspects of your journey (good and bad) with the community. It's inspiring!

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      Thank you so much! I appreciate the kind words... Okay I'll keep sharing my journey with you guys : )

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        Yes! Please do. Wishing you the very best of luck and rooting for you hard.

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    And you managed to learn all this in 30 days? Congrats! Took me years...

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      Hey Yasha! I guess so. It's all a learning experience right : )

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    It took me forever to create a routine for myself. Can’t agree more how important it is!

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      So true! It helps right? Kind of like the work day ... but you're working for yourself : )

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      Couldn't agree more. If I fall off my routine even one day, the day NEVER goes well no matter the reason for the slip.

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    I agree with everything you said above. As a beginner indie developer i found it really hard to make something out of nothing on your own. Especially I start to loose my motivation after working couple of days on the project. As I start to work on the project I find out other people doing the same thing. And at that moment I start to think about doing something different or just move on to another project.

    1. 1

      Thanks Deebov, I appreciate the kind words. Keep pushing mate! : )

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    Ohh man, give me a break. What if I live in India, can those things compete. I was happy with our local Administrative Programs. https://hrex.org/nrega-job-card shared every 100 days with new card jobs where each jobs description was written down, and they are for rural workers. I was so happy for it after two months of absolute isolation. Now the situation is much more better. I like my job for past 3 months and I don’t want to change it. Soon I will need another car job. There are four types of job cards - Combined Time and Job Cards, Simple Job Card, Job Card Issued for Each Job, Piece Work Card, so I will think I need to change to another one.

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    Have a dedicated workspace

    There's a nice trick i picked up during my first startup: Reach out to other startups in your city that have their own office.
    Email the founder, explain what you're doing (be humble) and ask him/her if they are willing to host you for a month or two.
    You'll be surprised at how many people are willing to help.

    1. 1

      This is fantastic advice! Love this idea... as you said if you have the humble approach right? Nice.

  12. 1

    Good post!! @CraigBarber I was sailing two boats at the same time. I came to a point that, I need to quit my day job to venture opsmagic.com by keeping 3 months as a buffer same as you. But in reality, giving life and momentum to a product takes more than 3 months, but it's going to set me in the direction to get users.

    Good luck!! keep sharing your journey.

    1. 1

      " sailing two boats at the same time " - love this way of putting it.

      Yes, everyone keeps telling me how short 3 months is!? - I'm going hard and I'm prepared to accept the consequences - which means going back to my day job : (

  13. 1

    I would be interested in your project once it is ready. I did not sign up via email because honestly I would never check my email and see it.

    Anyways, are you going to eventually try to expand your market? It seems like your market could be so much bigger than what you are going for.

    1. 1

      Hey Captain! If you join my launch list you even get a FREE eBook I've written on how to name your next startup : )

      My market is specifically targeted at developers, indie hackers and side hustlers.

      When you're starting out, it's best to constrain your market as you can be much more effective... for example I'm not targeting people who want a fashion brand and want print decorative style logos etc. My audience wants logos they can use on their websites.

  14. 1

    Several years ago I had the opportunity to work full time on a side project when I got laid off.

    I was able to launch my iOS app in two months by going to the library everyday as if it was my day job.

    It was free, quiet, close to my house, and had enough human beings around that it didn’t feel lonely.

    So I felt like that worked well for me.

    Anyway, great post and good luck!!!

    1. 1

      Nice work! great to hear a success story : )

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    Thanks for sharing. I just joined your launch list. I also recently left my job to work full time on scribbl.co so I can relate!

    Keep pushing man!

    1. 1

      Great work! Yes, let's keep pushing : )

  16. 1

    Thanks for the write-up!

    How did you decide on the right time to leave your job? Sounds like Logobly was already fully launched?

    Wish you the best of luck!

    1. 1

      Hey there, I left my job cos I'd had enough already : )

      I decided to take a stand, it's the old... if not now... when?

      No Logobly.com has not launched yet. It will be ready in a couple of weeks.

      Thanks for your support.

  17. 1

    This is great advice. I want to quit my job and do the same thing but I have many fears. Unless I have a working product to take to the market, I doubt even my family and friends would care but I believe building a community around my product/ idea is essential to my growth. Maybe I'll get some juice and just make the jump into the startup world here soon.

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      You have to have a pretty chunky product to work on I believe. You can spend time at the start working out what that is... then it's time to get to work and make the money maker : )

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    I'm right there with you - it's been 3 weeks for me. I definitely agree with being healthier. Also, since I am working from home, i get to spend breaks with my kids and I feel like I am spending more quality time with them now than when I had the ol' 9 - 5.

    Good luck on the logo maker! Hopefully, you get some income coming in so have more runway to keep at it!

    1. 1

      Great to hear! Yes, it's surprising right? And yes I'm a lot closer to my family too : )

      Thanks for the kind words, and yes 3 months is short - but hey that's the game right.

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