Before Quitting Your Job, Read These 35 Startup Tips

April 21, 2015

2:00 pm

The startup life is alluring for many; in particular, it’s a goal desired by those wanting to work for themselves. However, while the prospect of having no boss and working according to one’s own terms is certainly enviable, the entrepreneurial life has with it many downsides – in the end, quitting your job to pursue your entrepreneurial endeavors could actually f*ck up your life. That’s not to say, though, that such ends are predestined; rather, before taking the leap, it’s important that you take several factors into consideration so that you’re well-prepared (or, at least, somewhat prepared) for everything that the startup life has in store for you.

Ross Simmonds offers his own 35 startup tips for people hoping to leave their jobs and launch their own ventures. In a post published yesterday on r/entrepreneur, Simmonds reflects on the experiences that led up to his starting a consulting business, as well as cofounding a subscription service company. Simmonds understands the risks associated with leaving behind the safety provided by your standard corporate job – I mean, he had to do it himself; however, he’s also learned that there’s ways through which people can prepare for the life of an entrepreneur ahead of time.

A follow-up to an equally successful post on how he managed to build a $250,000 consulting business in two years, Simmons writes the 35 things he wish he would have known before quitting his job and pursuing the life of an entrepreneur. Despite his own success with his venture, such success is often rarely replicated by many, and Simmonds merely hopes to help others in reducing their risks and increasing their chances of success. In many ways, it’s a preview of Simmonds hopes to offer in an upcoming guide he’s currently working on, The Hustle Manifesto: Escape the 9 to 5 in 6 Months. As a quick primer, we’ve included a few of his tips below:

  1. Learn to say no more often than yes. Lots of opportunities will come up but picking the right ones is more important than saying yes to everything and not being able to give the important opportunities as much effort and time they deserve.
  2. Expect things to go wrong. Everything. It might not actually happen but this mentality will help ensure you’re prepared and doing the best you can to keep things on the right track.
  3. Just ship it. You’re going to be your own worse critic. It’s easy to become paralyzed by critiquing your own work – Just ship it. Whether it’s a blog post, proposal, email campaign or media outreach – JUST SHIP IT.
  4. Create a “Kill List” that highlights the various items you need to do the next day every night before bed. Start with the most difficult items and cross them off your list one by one as you do them.
  5. Learn to handle criticism. Never take it personally. Whether it’s a project or an idea – isolate the criticism from yourself as an individual and recognize that it’s a vehicle for you to improve. This post from James Clear is a great one for this.
  6. Charge what you’re worth. This course from /u/BrennanDunn is spot on and will help change the way you look at pricing your product or service.
  7. Spend less time with talkers and more time with doers. Lots of people will talk about what they are going to do in the future. Few people actually step up and take action. Spend more time with those who take action and it will rub off on you.
  8. Keep your mental health in check. Entrepreneurship is filled with highs and lows. It’s filled with Gutters & Strikes as Tomasz Tunguz once said. Stay sane through personal reflection, spending time with great people, journaling, meditation, etc…
  9. Read the following books: E-Myth Revisited, Getting To Yes, The Black Swan, Good to Great, The Power of Habit.

Read all 35 of Ross Simmond’s tips before quitting your job on Reddit.



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Ronald Barba was the previous managing editor of Tech.Co. His primary story interests include industry trends, consumer-facing apps/products, the startup lifestyle, business ethics, diversity in tech, and what-is-this-bullsh*t things. Aside from writing about startups and entrepreneurship, Ronald is interested in 'Doctor Who', Murakami, 'The Mindy Project', and fried chicken. He is currently based in New York because he mistakenly studied philosophy in college and is now a "writer". Tweet @RonaldPBarba.

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