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Practical Advice for Making The Leap From a Well Paying Job to Full-time Entrepreneur

  • Thomas Oppong
  • Jun 12, 2015
  • 5 minute read

Most people hate their jobs and want to quit but don’t have a better alternative. Those who have great options can’t make a decision. They can’t get out of their comfort zones just yet. Others want to start their own businesses but don’t have the courage to make the leap from that well paying job to a full-time entrepreneur. You can never be ready enough. It’s one of the toughest decisions you can ever make. Given up your financial security for an uncertain future is not an easy decision to take.

If you have ever thought about given up your 9 to 5 job for an entrepreneurship career, this post is exactly what you need. These are practical lessons, advice and tips from reddit users who have made the leap.

1/ Fear of failure is your biggest obstacle.

“Let me tell you something: if you’re afraid to fail you’re going to be stuck there forever.

For years I stayed in awful positions because I was comfortable and scared shitless that I just couldn’t do it. I’ve moved from shitty jobs to consultancy to doing this full-time – my life isn’t perfect but I’ve found amazing meaning in my work and helping people have the best damn business they can.

You can do this OP, even if you have to ease into it gently.

You should offer your services here on reddit in one of the subs (/r/Entrepreneur comes to mind) on the business side of things for a developer or someone else that needs the help and see what happens. If you’re not cut out for it, you’ll know and you’ll be able to stay in your job. If you are cut out for it, you’ll keep consulting until you’re ready for the thing that sets you free.” says terpin.

2/ Plan for it before the all important leap.

“Think about the worst thing that can happen if you leave your job and go for a startup… then realize that the worstthing probably won’t happen, and it could be a range of good to great things.

Also, set yourself up to leave your job. Start living mega-frugal so you can save a bunch of money over the next 6 months or year so you can have a good cushion to be low paid for a while. Cancel TV service, downgrade your internet to the slowest you can tolerate, stop drinking alcohol, cook for yourself & eat in, bring your lunch to work, stop buying clothes, pay off your consumer debt, switch to one of those $25/month cell phone companies…

The average well paid American/westerner can pretty easily cut spending by hundreds of dollars a month. Start doing so now, so you can get extra money in the bank, and be used to living on less when you may not have a choice later with a startup.”-OskarBlues

3/ If you’re not committed, DON’T take the leap.

“Consulting gig is a common stepping stone. I will tell you though unless you’re committed, DONT. Its a crazy hard road with a whole lot of turbulence. I’ve advised and overseen numerous startups and the ones that flop are those that fail to have commitment to purpose.

So if you’re going to do it, get a plan, get as much ready as you can, have a first month and 3 months planned out (it’ll all go to shit but it gets you thinking the right way). Then really decide you are doing it. B/c without decisiveness your chances of failure are so much higher. And the first 3 years are not glory and fun. They are a seriously hard slog that will test you, your flexibility and most importantly every one of your personal weaknesses.

But as an aside, you will fail. Every entrepreneur fails along the way. Its how you learn from your mistakes and carry on that make the difference. You’ll only truly Fail when you give up.

Final edit: If you need advice specific to your situation feel free to PM me. Like I said I’ve advised and run multiple startups. I have a non-profit where we teach people in your situation how to make that leap and then if the fit is right we also fund them. Its locally focused so I wont be able to help you in the financial aspect but Im more then happy to share the insights.”–senjutsuka

4/ Dump your limiting convictions if you are convinced about what to do.

“I have jumped right off the cliff since the beginning of my career, because I have always been convinced that I needed to build my own company and not work for anyone else (I had to for 1,5 years because I had no more cash, but other than that I have managed this for over 10 years).

What I have learned is that it’s actually not bad to have something ‘on the side’. For 1 reason mainly: you can experiment with the idea that you have. Nowadays, most startups follow the lean startup methodology. You can build an MVP and test whether your assumptions are right. And usually, it takes time to get that MVP and your first user feedback going > I think that’s something you can perfectly do while you have a job.

Dump your limiting convictions. If you’re afraid, do it on the side. If you’r not, quit your job. You’ve got only 1 life, I don’t see why you wouldn’t do what your heart tells you to….” says hugomesser.

5/ If it’s what you need to improve your life, plan for it and make a decision.

“It’s a very hard step to make, but it is possible and actually very satisfying. I did something similar last October where I left a pretty well paid job as a recruiter for a big market research company, but took the plunge and go freelance full time. I appreciate this isn’t exactly the same as starting a company, but the prospect is similar and also feels like jumping off a very large cliff with no parachute. The main thing is to have money saved so that if you do decide that you’re going to do it, you won’t be instantly broke. The other thing is to get the other project you’re leaving your job for rolling well ahead of time so that the transition is smooth.

Ultimately, only you will know if you’re doing the right thing with your time, be it sticking to what you do now or flying solo, but if you do take the decision to leave your job, do it carefully and only when you know that it’s what you need to do to improve your day to day life.” says SquidYesNotSoOctopus

Follow this topic on reddit here.

Thomas Oppong

Founder at Alltopstartups and author of Working in The Gig Economy. His work has been featured at Forbes, Business Insider, Entrepreneur, and Inc. Magazine.

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