Ever wondered if it’s time to trade in your day job for your dream business? Learn from top professionals like a Principal and a Founder and CEO, who share their valuable insights. This article kicks off with the essential advice to research thoroughly before quitting, and wraps up with the crucial tip to write a detailed business plan. Discover eleven practical insights from industry experts that can help you make the leap successfully.
- Research Thoroughly Before Quitting
- Ensure Financial Runway for 6–12 Months
- Develop a Financial Transition Plan
- Assess Your Business Skills
- Validate Your Business with Real Customers
- Discover a Purpose That Drives You
- Establish a Robust Financial Foundation
- Take Small Steps Towards Your Business
- Consider Your Financial and Mental Health
- Evaluate Your Personal Risk Tolerance
- Write a Detailed Business Plan
Research Thoroughly Before Quitting
When is the right time to quit your job and start your own business? That’s not until you’ve thoroughly researched everything about the new business and the move, looked at the upside and the downside, and figured out how long it might take you to become successful at it. In many cases, you may need to work out how you’re going to meet your financial obligations in the meantime.
A certain amount of fear is healthy; it inspires caution and helps keep your planning realistic. If you want your dream to come true, examine it with your eyes wide open in the cold light of morning.
Barry Maher, Principal, Barry Maher & Associates
Ensure Financial Runway for 6–12 Months
From my experience working with numerous founders, I’ve noticed there’s rarely a “perfect” time to make the leap. Looking at my own career path, I made calculated moves—from N26 to Civey, then to Deutsche Bahn, and eventually founding my company while I was at Deloitte.
One critical factor that I always emphasize to potential founders is having enough runway (savings or alternative income) to sustain yourself for at least 6–12 months. This is particularly important since that 38% startup failure rate due to running out of cash I often mention isn’t just about business funds—it includes personal financial stability too. I actually started my business as a side hustle while at Deloitte, which gave me the security to test the waters and validate my business model before going all-in.
This approach allowed me to build a client base and refine my service offerings without the immediate pressure of needing to generate full-time income. Just last month, I was working with a founder who did something similar—keeping their day job while spending evenings and weekends developing their business for six months before making the transition. Having that financial cushion made a massive difference in their ability to make clear-headed decisions without desperate moves due to financial pressure.
Niclas Schlopsna, Managing Consultant and CEO, spectup
Develop a Financial Transition Plan
When I work with clients who want to transition from employee to entrepreneur, we start with a financial transition plan. There are two critical financial inflections during this time that you need to account for:
- The expenses needed to start the business and the plan for revenue growth.
- The loss of regular income (via a paycheck) to cover monthly personal expenses (mortgage, food, memberships).
I always recommend starting the business and getting the basics in place while you still work and have a steady income. The initial administrative expenses can overwhelm new business owners, but they are necessary to establish your foundation.
Then, we focus on the product and service offerings and our revenue-generating plan. During the marketing and sales cycle, it can take time to attract attention to your offering. You need to land deals quickly and get feedback on that offer to understand how it’s received in the market. Then, you can decide whether the offer or target market is the issue and adjust accordingly.
Most people can manage the first year of business as a side-hustle to their day job. It takes careful time management and focus on your goals, but it makes a financially viable transition more likely.
Nikki Green, Life & Business Resiliency Expert, Green Chameleon Collective
Assess Your Business Skills
The right time to quit your job depends on your skills—not your job skills, your business skills. Do you know how to build a website? Do you know how to write SEO-optimized articles to gain traction on Google? Have you ever converted a lead into a paying customer? Many people are under the impression that being good at your job will translate into being good at business. Nothing is further from the truth.
Pretend your job skills are only 15% of what you need to succeed; then you’ll understand that the bulk of what your business requires are business systems and your own ability to execute. So get building, start writing, and you’ll be very happy once you get a paying customer from Google. Don’t use paid ads either.
Jeffrey Calderon, President, Permits In No Time Inc.
Validate Your Business with Real Customers
When real customers are willing to pay real money for your product/service, you have a real business. Start with the fundamentals: Who are you and why should anyone care? If you’re not passionate about what you’re doing, then why should anyone else be? If you don’t have a unique story to tell and a new approach or idea that excites you, then go no further. Every great business is built on a great story, so start telling yours to potential customers and see if they buy what you’re selling. Testing should always be done with real customers, not with family/friends (who may only tell you what they think you want to hear, so they don’t hurt your feelings).
Create evangelists who know how/where/why to buy from you. If you’ve already built a fan base for your new business, you’re one step closer to your grand opening. This set of people who support your idea will help you find your early customers. It’s critical to know your target audience, understand what matters to them, do your market research, and refine your message to stay relevant to their needs. Listen to the feedback they give you, even if it’s not what you want to hear. It’s about building rapport, trust, and ultimately a relationship.
If the days (and nights) fly by and you have more ideas than time to address them all, you’re moving in the right direction. If you can’t shut off the stream of ideas you’ve got to make your business a success, it’s probably time to start acting on them. But make sure you prioritize/focus on the crucial ideas so you don’t get distracted. There’s no substitute for doing your homework so you can be ready and aware when serendipity strikes. The important thing is to keep moving forward and learn from every experience. You can’t wait for the perfect time to launch; you just have to course-correct as you get more feedback along the way. Being an entrepreneur means making decisions without perfect information. Get used to it—or keep your day job.
When you believe in your core that a bad day on your own is better than a good day at your desk job, you’ve got nothing to lose. Failure was never a consideration for me despite the fact that most startups fail. My business successfully leveraged my relationships and prior experience, so it really felt like the culmination of years of training for this opportunity. If you’ve made it this far, you owe it to yourself to give it a shot. If I haven’t scared you off yet, you may be ready to launch.
Paige Arnof-Fenn, Founder & CEO, Mavens & Moguls
Discover a Purpose That Drives You
The right time to quit your job and start your own business isn’t a magic date on the calendar; it’s when you’ve discovered a purpose that won’t let you go. Starting a business isn’t easy, and the challenges will test you, but if you’re driven by something that matters deeply, then you’ll have the resilience and focus to push through.
One crucial factor to consider: make sure you’re clear on four critical questions: why you do what you do (belief in your future mission), how you will uniquely differentiate and position yourself in a new and innovative way, what services/products you intend to provide that make good on those previous two questions, and finally, and most importantly, who you’re trying to help and why your vision will make a meaningful impact in their lives.
If you’ve got the clarity and conviction to make the leap and stay the course, you’re already well ahead of most!
Chase Friedman, Founder & Brand Purpose Coach, Vanquish Media Group
Establish a Robust Financial Foundation
There is never a “perfect” time to leave a stable career and venture into entrepreneurship. However, there are critical steps you can take to determine the optimal timing for launching your own business:
- Financial Foundation – Establish a robust emergency fund covering 6-12 months of expenses. This buffer is essential, as most businesses experience gradual revenue growth in their initial phase. Your financial cushion should account for both personal and projected business expenses.
- Business Plan and Cost Analysis – Leverage your state’s small-business development resources. These organizations offer complimentary consulting services to help develop comprehensive financial projections and business plans. Understanding your operational costs, market analysis, and capital requirements is fundamental before launch.
- Revenue Projections – Conduct a realistic assessment of your earning potential. While some businesses achieve profitability quickly, most require 2-3 years to establish stable, substantial revenue streams. Consider whether you can maintain your desired lifestyle during this growth period, even if initial earnings fall below your current salary.
- Motivation Assessment – Evaluate your core motivations for entrepreneurship. Are you seeking: a) greater income potential, b) professional autonomy, c) work-life balance, or d) career fulfillment? A thorough analysis of your motivations and a detailed pros/cons assessment will help validate your decision and maintain focus during challenging periods.
- Hybrid Transition Strategy – Consider maintaining your current position while launching your business. This approach, often called a “side hustle,” allows you to build momentum while retaining financial stability. You can gradually scale your business operations as revenue increases.
I implemented this strategy in my transition from health care to entrepreneurship. By initially operating my business part-time, I minimized risk and gained valuable experience. The University of Georgia Small Business Development Center provided essential guidance throughout this process.
While my current income doesn’t exceed my previous health care salary, the increased flexibility and professional satisfaction have proven invaluable. Despite inevitable challenges, entrepreneurship has been tremendously rewarding. With proper preparation and realistic expectations, pursuing your business aspirations can lead to both personal and professional fulfillment.
Candace Hires, Owner, Candace Hires Photography
Take Small Steps Towards Your Business
There is no one right time for everyone. Being able to quit a job and start your own business is a financial privilege. You need to consider the financial consequences losing your steady income will have on your lifestyle. You will not be making a profit immediately, so having a financial safety net for the first year is important. I would not look at it as one action but rather many small steps.
Perhaps you can start putting things in place for your new business while maintaining the security of your current job for income. Perhaps you can take some business classes before completely quitting, or join a networking organization to start getting your name out there. Small steps can be taken as you save for your safety net.
Jordana Avital, Owner, Poly Speak LLC
Consider Your Financial and Mental Health
While everyone’s situation is different, I think it’s important to consider your unique financial situation as well as your mental health in your current job. In my own experience, the best time for me to quit my job and start my own business ended up being before replacing my full-time income with my business income. Some people are able to slowly build their business on the side and slowly phase out of their day job, but after eight years of trying to do that, I learned that I’m the type of person who needs to fully let go of one in order to give everything I have to the other.
Additionally, my mental health was suffering due to the exhaustion from my demanding day job and trying to build a business at the same time, so I knew it was time for me to leave. And so I made a plan! While still at my full-time job, I started to get some business tasks in order, such as creating an LLC for my food-photography business, getting a business bank account, and deciding on a business name and logo. A few months later, I communicated with my employer my plan to leave and ended up working a few months part-time before fully parting ways.
It’s important to note that I was able to build some savings prior to doing this, so that I can continue to support myself for a bit while building my business. Even though I’m taking a temporary pay cut, I’ve gotten the gift of time back, so I can now create my own career and build the creative life I always dreamed of.
Tera Gigot, Food Photographer & Content Creator, Roots and Radishes
Evaluate Your Personal Risk Tolerance
There’s never going to be a “right time.” Everyone’s “right time” is going to be different depending on their personal risk tolerance, living situation, and finances. For me, the right time was when I moved abroad and didn’t have the option to keep my job; it worked out that my personal expenses were low, and I could afford to take that risk. Eleven years later, and here I am still working for myself.
But, if you have a less-than-supportive spouse, or kids, or lots of debt, you may need to wait until you have support, more time, and less debt.
As far as the one important factor to consider, it is your personal level of risk tolerance and anxiety. Starting your own business is stressful, time-consuming, often confusing, and sometimes deflating. There’s a lot you can do to mitigate that while still working a full-time job, so getting the wheels in motion while still having a steady paycheck is going to save you a lot of headaches down the road.
Ashley Hill, Marketing Consultant and Web Designer, ashleyidesign
Write a Detailed Business Plan
Write a proper business plan and take time to do some business research to make sure your target income is realistic and achievable. Ideally, carve out some time to start the business alongside the day job and only quit once you’ve established the new business is viable. This might mean working late nights and weekends for a while but will greatly reduce the risks, especially if you don’t have enough savings to support yourself until your own business is established.
It’s time to quit when things are looking very promising for the new business and the main thing still holding it back is your day job. Eighteen years ago, I turned my passion into a business, and I haven’t looked back! As a photographer, I was able to work weekends and build up my client base until I felt confident enough to leave my previous job as a software developer.
Stephanie Belton, Photographer, Stephanie Belton Photography Ltd
