Should I Quit My Job To Start My Own Business?

It’s the first and most important question every would-be entrepreneur asks themselves: Should I quit my day job to start my own business? We turn to three experts to sort out if it’s the right time to take the leap.

Should I Quit My Job To Start My Own Business?
[Image: Flickr user Araí Moleri Riva-Zucchelli]

When you hate your job the idea of jumping ship to start your own business seems like a no-brainer.


But if you have a well-paying job you actually like the question becomes a little more tricky. For this week’s question we turned to leadership coach Lolly Daskal, Leo Widrich, the cofounder of social media app Buffer, and resident entrepreneur at the United Nations Foundation (and Most Creative Person) Elizabeth Gore.

I am 28 years old and I have a solid career path. I have a management position with a great team, and I make a comfortable living. However, I recently started dabbling in a side venture to start my own business. It ended up not working out, but now I am wondering what I should do: Stay the course in my current career or jump off the ledge and commit fully to doing my own venture?

I think my problem is trying to juggle too many things at once, if I focused all my efforts on one, I think I could succeed.

Appreciate any and all thoughts on this matter.

Your truly,


Without having much detail on what kind of venture, it is hard to help you think through the best solution in your particular situation. But in general, for a person who is trying to start a new venture and wondering if they should quit a current lucrative position, my short answer is no.


As a business consultant I always coach my folks never to leave one job or business before their new venture is successful and lucrative. Otherwise it can lead to a roller-coaster ride. I believe you can use your current day job as a springboard to your new venture if it is done right.

The best you can do is to create a plan that literally funds and creates your freedom. Here are some basic points to get you started:

Ask the right questions.


Ask yourself questions to make sure you’re thinking about the right key business decisions and are on point about what you are creating.

  • Why am I starting a business?
  • What kind of business do I want?
  • Who is my ideal customer?
  • What products or services will my business provide?
  • Am I prepared to spend the time and money needed to get my business started?
  • What differentiates my business idea and the products or services I will provide from others in the market?
  • Where will my business be located?
  • How many employees will I need?
  • What types of suppliers do I need?
  • How much money do I need to get started?
  • Will I need to get a loan?
  • How soon will it take before my products or services are available?
  • How long do I have until I start making a profit?
  • Who is my competition?
  • How will I price my product compared to my competition?
  • How will I set up the legal structure of my business?
  • What taxes do I need to pay?
  • What kind of insurance do I need?
  • How will I manage my business?
  • How will I advertise my business?

Write a business plan.

Every successful venture has a business plan, a written description of your business’s future. That’s all there is to it–a document that describes what you plan to do and how you plan to do it. You can find a wealth of good business plan templates and models online.


Become two people at once.
You mentioned that your current job is a good one. To stay where you are while also pursuing your own business you need to become two people: one who is currently successful, working at a great job with great people, and another who follows a very strict plan with deadlines and goals every day to make your new venture–your freedom plan–is a success.

Customize your time.
Time is one of your most precious resources. To gain serious momentum for your new venture, learn to customize your time with SMART goals:

  • Specific: Know exactly what you want to accomplish.
  • Measurable: Know how you will demonstrate and evaluate the extent to which the goal has been met.
  • Achievable: Make yourself stretch, but not beyond your abilities or time frame.
  • Relevant: Tie your goal to your key responsibilities and objectives.
  • Timely: Set target dates for goals and subgoals.

Work your ass off.
Starting your own venture is not easy. But working hard every day and taking action one bold step at a time will bring you steadily closer to making it happen.


Get help.
Hire someone who knows how to get you from where you are to where you want to be. Holding on to your steady corporate paycheck can help give you funds to hire a coach to help you with time management, business planning, and preparing you for the ups and downs of entrepreneurial success.

Build a safety net.
Until you are able to establish a solid stream of income from your side business, you don’t really want to quit. When you’ve got a few months of expenses stashed away in the bank, you can feel freer and not as fearful about moving forward. Even if things don’t work out, you know you can survive. With a safety net you can be bolder with your decision making and take more risks. It makes work much more satisfying when you know you are putting your freedom in the bank.

Deal in patience.
Everything worth having takes time, and patience, passion, and perseverance are important foundational elements for an entrepreneur. When you deal in patience, you can take steps every day to work on doing something to improve, build, and construct your new venture.


Set a date.
Lay out a plan to build up your side business into a full-time gig, and highlight the specific date you want to quit on your calendar. Give yourself an incentive to have your new venture up and running by the date you’ve picked.

Make quitting your current position happen sooner than later, not with a risky leap but by following a great plan with smart goals and bold implementation, with help and patience.

Let me know how it goes.


Hi Kevin,

When you are lying awake at night and you can’t stop thinking, or sitting at your current day job, craving being your own boss, how do you channel that anxiety into strategic questions for how to move forward? Let’s break down these thoughts into the three Ps: Passion, Payments, and the Public.

Do you have the passion and drive–the shear will–to launch your company? Being an entrepreneur takes a lot of grit. It is critical to ensure you have the energy to drive forward your own agendas. You will be a giant company of one on your first day–that will grow–but it is on you at first. Make sure your personal life can uphold what you are about to take on. Success starts with you as a leader.


Do you have enough cash flow to pay the costs of your business, your bills, and to buy food? Whether you are bootstrapping, have investors lined up, or are lucky to have funds from your family–build a budget before you jump. What are the costs associated with building your company? Be sure to remember your personal costs as well. You are leaving behind a salary and have to pay yourself. Finances and cash flow can be the most stressful part of both your business and personal life–so think this through deeply.

Is this the right moment to launch with your future customers? Timing is everything and is driven by the public ability to pick up a new technology, product, or behavior. You might have the greatest idea and enough funding–but what is the appetite of the world around you? This question is not as black and white as the first two. But it is important to understand consumer trends, competition, and the overall status of the economy and industry you are in.

Hi Kevin,


How do you go about quitting your job, quitting college, or anything else to go on doing that thing that you always wanted to do? The question is probably one of the hardest one to go about finding a suitable answer to that doesn’t sound outright crazy. It’s in fact such a hard one, that I often see people avoid the question, forever.

I quit college to start my own business. Here are a few things I’ve learned:

Using the Tarzan technique to quit your job

One of the absolute best descriptions of quitting your job with the least risk, is the “Tarzan technique,” that Derek Sivers, one of my favorite writers, has so eloquently described before.


“Remember how Tarzan swings through the jungle? He doesn’t let go of the previous vine until the next vine is supporting his weight.

So my advice is: Change careers like Tarzan. Don’t let go of the old one until the new one is supporting you. And make sure you don’t lose momentum.”

We sometimes live with the illusion that “if I had just more time to focus on my side venture, it would definitely succeed!” The truth is, at least in my own experience, that having a limitation, both in terms of time and money, around your side hustle can actually be a good thing. It forces you to heavily prioritize and become extremely structured about your decisions.


When we look at things in detail, I found that there are often a few other factors at hand too.

Reducing other commitments first
When people consider “quitting their job, to work on their dream idea,” the first thing that I always think about is, whether there is a chance to quit other things first, that might not be as vital as your job to support yourself or your family.

When we look at our lives, we often have a huge number of different commitments, that aren’t tied to paying the bills. Starting with reducing some of these first, might be a better way to go, instead of axing your job. If you have five different hobbies that you want to all keep up with, it might be worth letting go of some of these, to make some time to work on your side project that could eventually turn into your company or new job.


Try making a list of all the things you’re doing in a given week and think hard on each of these, whether you should keep doing them, or whether there’s a chance to dial back on them a bit, at least for the time being.

Examples of making career changes like Tarzan

So, how can you make sure that you don’t let go of the old vine, if the new one isn’t quite supporting you yet? There are a few ideas, that I’ve come across that might be helpful:

Work early mornings instead of evenings
Joel, my cofounder and CEO at Buffer, discovered an amazing technique that helped him succeed and launch the first version of Buffer, whilst he still had a full-time job:

“Eventually, I had a big breakthrough which I attribute a lot of my early success to. I realized that I was often trying to work on Buffer in my evenings, after a whole day of work for other people. I wasn’t fresh at all, I was often very tired and unproductive. So I reversed things–I started waking up much earlier (around 6 a.m.) and worked for 90 minutes before I started my freelance work, while I was completely fresh.”

This is a change so simple, and yet so often overlooked. We sometimes think of just putting in the extra hours in the evening to work on our own success, and yet, when our willpower is depleted and we’re tired, we’re facing an uphill battle, that most of us ultimately don’t win. Changing your routine to mornings can be a great help.

Take a sabbatical at your job, or even an extended vacation
If you still feel that you need to really go all in on your idea, things I’ve seen work with others before are a sabbatical for a few months. If that isn’t an option with your current employer, taking an extended vacation, for as long as you can, could be a great start on where you’re going with your idea.

Go chase your dreams, Tarzan-style, from one vine to the next!

If you have a dilemma you’d like our panel of experts to answer, send your questions to or tweet us a question using #AskFC.