35 Things To Know Before You Quit Your Job For Entrepreneurship

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It’s been two-and-a-half crazy years since I put in my two weeks notice and left the nine-to-five once and for all.

It was a crazy time in my life, as I had just bought a home, but I was completely tired and drained from working for someone else.

I knew I had to escape the nine-to-five and I was determined a few months earlier to put the steps in place that would allow me to make it a reality.

Over the last two years, I’ve built a consulting business that, last year, made more than $250k in revenue. I share the figure because I want people to know I’m by no means on the level of Mark Zuckerberg or any of the folks on "Shark Tank," but that I’ve reached a point financially that has allowed me to live life on my terms.

I’ve been able to make investments into projects I’m passionate about like Hustle & Grind, Slideshare presentations and a few other things I plan to launch in the upcoming months.

The last two years have been filled with highs and lows. I wouldn’t change it for the world, and I’m thankful I’ve been able to grow and have great people around me.

If it weren't for my clients, partners, family and friends, I would likely have burned out many months ago and not be writing this post. So thank you.

For anyone else stuck in the nine-to-five and looking to escape, I’m writing a guide called The Hustle Manifesto that can change your life. It’s not just a guide, it’s a resource pack filled with stories, email scripts, cheatsheets, webinars and clear insights I’ve gathered over the last few years.

I’m also including a handful of interviews from other people who have escaped the nine-to-five to create their own businesses. I hope you check it out and preorder while it’s available.

Now, let’s get to it. Here are 35 things I wish someone had told me before I left my nine-to-five:

1. Learn to say no more often than yes.

Lots of opportunities will come up, but picking the right one is more important than saying yes to everything and not being able to give the important opportunities as much effort and time as they deserve.

2. Start building relationships way before you decide to quit.

These relationships are going to help you more than you know down the road. You don’t have to plant seeds that you’re looking to quit your job, but show these people that (1) you care and (2) you can help them.

If you do that, they will help you when you need them most.

3. Invest in yourself and your future today.

Don’t wait to read books and blog posts on entrepreneurship or accounting until after you quit.

Read now while you’re employed and have a steady paycheck so you’re not scrambling for this knowledge when you should be building your new business.

4. Expect things to go wrong.


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.

5. Maximize revenue, minimize costs.

Sounds like basic business advice, but too often you will find entrepreneurs forgetting the importance of keeping costs down.

I’m not saying nickel-and-dime people, but don’t be afraid to ask for lower rates on software, banks, credit companies and when working with established suppliers.

6. Everything needs more time.

Everything takes longer than you thought at first. Once you get a few projects under your belt, it will be easier to estimate timelines.

7. Save cash before and after you quit.

Keep a couple thousand dollars in a separate bank account for a rainy day. Trust me, rainy days will happen.

And before you quit, make sure you have three to four months runway in projected revenue or in the bank.

My approach was simple: lock in one client that would allow me to cover my mortgage and hustle like crazy to get more work ASAP.

8. The phone isn’t your enemy.

As much as you might hate talking on the phone, some of your clients and partners will prefer it.

Make it a habit to pick up the phone and call someone instead of relying on email, text and instant message. This is more of a Gen-Y issue than anything else.

9. Just ship it.

You’re going to be your own worst 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.

10. Take on amazing clients and projects as early as possible.

These projects and clients might not pay as much, but during your early days, it’s important to take on work that will help differentiate you from the crowd.

11. Embrace the right tech.

Streamline your workload with the right technologies in place.

Use a tool like Freshbooks for invoicing, Basecamp for managing projects, Dropbox for storage, Proposify for proposals, WP Engine for your website hosting and Slack for communicating with partners and suppliers.

12. Hack your inbox with tools like Boomerang that will help you schedule emails to go out at a later time.

People don’t like emails at 2am, so use Boomerang to schedule it to go out at 8am the next morning. Other tools include

13. Multi-tasking is a myth.

You get more done by simply focusing on one thing during a set period of time instead of attempting to do two or three.

14. 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.

15. Make goals and revisit them every month.

16. Don’t be afraid to ask for help.

17. Don’t be afraid to ignore some advice.

It’s not all good.

18. Remove distractions to prevent procrastination.

Don’t work in the living room because you’ll make the mistake of turning on the PlayStation. Don’t work in the kitchen because you’ll attempt to cook something delicious.

Work in a place where your focus is going to be on the work.

19. 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.

20. Charge what you’re worth.

This course from Brennan Dunn is spot on and will help change the way you look at pricing your product or service.

21. Know at least two good jokes

...Or stories you can share in practically any situation to lighten the mood.

22. Keep your word and embrace those who do the same.

23. It’s okay to delegate.

People who help you might do things differently, but they will still get it done.

It might not be exactly the way you wanted, but sometimes, you just need to walk away and let people learn on their own and do their own thing.

24. Drink more water.

25. Don’t take on projects you don’t believe in and not at a discount.

The opportunity cost is too high. If they’re haggling for a lower price point, it’s likely they don’t value your work as much as a client you actually believe in.

And if you say yes to this project, you won’t have time to take on the work you believe in.

26. 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, but few people actually step up and take action.

Spend more time with those who take action, and it will rub off on you.

27. Meet more people.

Go to events, but don’t spend all your time hanging out with the same folks.

You build your net worth by building your network, so meet new people.

28. 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, meditating and more.

29. Public speaking is a great tactic.

The conversion rate at events for new business is higher than the conversion rate of tweets and LinkedIn updates.

30. Streamline your processes.

Create a proposal and process at the beginning that can be used in a cookie-cutter manner from one client to the next.

The steps you take to onboard a client should be so straightforward and automatic that someone else could come in and run that process without you.

The goal here is simple: Create a business that could, someday, run without you.

31. Spend time understanding how to give effective feedback.

This article is worth reading.

32. Challenging work is the best work.

When you take on a project that sounds very challenging , you’re either going to do something awesome or learn something new.

Say yes to challenging work because it’s going to look amazing in your portfolio when you’re done.

33. Invest in people who invest in you.

34. Get a good lawyer and ensure your contracts are solid.

35. Read the following books: "E-Myth Revisited," "Getting To Yes," "The Black Swan," "Good To Great" and "The Power Of Habit."

I hope these insights help you with your journey into entrepreneurship.

Quitting your job can be an exhilarating experience, but it can also be the best move you’ve ever made.

If you’re thinking about the jump, comment below and let me know what’s stopping you. I’d love to help give you the insight you need to make the leap!

Ross Simmonds writes at, where he shares research-backed studies and his personal perspective on entrepreneurship, life, communications and technology.

To get his thoughts and insight delivered directly to your inbox and help your career and life go from zero to 100, join his free newsletter.

This article was originally published on Ross Simmonds' LinkedIn.