Many people ask me whether it’s better to be fully prepared before quitting a job to start a business, or to just leave and figure it out as you go. Honestly, there’s no perfect answer. But if you’re thinking about stepping out of the corporate world, freelancing, or launching your own studio, there are some things you really want to clarify as early as possible.
Some believe quitting first is the only way to fully commit to entrepreneurship. Others think it’s wiser to keep your day job while building your business on the side to reduce risk.
Personally, I left my full-time job to freelance and start my business only after becoming a father. Even with plenty of preparation, I still faced many unexpected challenges once I took the plunge.
Here are some key preparations I believe you should have in place before quitting your job to start a business. You don’t need to tick every box, but each one will definitely come in handy down the line.
1. Clarify Your “Why” for Quitting
Is it for more freedom? To escape management? Because you have a product or service idea? Or simply because you’re burnt out?
Your true motivation will shape how you make decisions later. When income drops, clients are scarce, and anxiety creeps in, your “why” will be the reason you keep going.
For me, there were several reasons. First, the work had become monotonous and unchallenging. Although I used to be involved in early product planning, the team had several product managers steering the direction, and my role gradually narrowed to UI only. I missed the sense of achievement from building a product from scratch.
Second, I wanted more hands-on management and leadership experience, which my previous company couldn’t offer. I couldn’t see a future or career growth there. Starting my own business meant I could create opportunities myself, collaborate with different designers, and manage resources and quality from a business owner’s perspective.
Third, as a father, I wanted more time to be involved in parenting. I take care of my child from around 6 or 7 am until 9 am, and also handle bath time and bedtime. Traditional 9-to-5 hours don’t suit family sharing.
Fourth, in terms of future plans, I want to live a “dual-city life”, spending winter in Taiwan and the rest of the year in the UK. Remote work and flexible freelancing are my goals. I have permanent residency and am waiting for citizenship, so no work visa pressure.
Fifth, I see entrepreneurship as my gap year. As I get older, I’ll likely seek more stability, but I believe most people harbour a dream of starting something of their own. I want to try stepping out of my comfort zone and explore another way of life.
📝 Tip: Write down your reasons for quitting and ask yourself: “If I haven’t earned money after a year, will I regret this?”
2. Save an “Emotional Buffer Fund”
This is not your startup capital, but a financial cushion to stabilise your emotions. Early-stage entrepreneurship usually means unstable income. You may doubt yourself, worry about the future, or even consider returning to employment.
If you have at least six months’ worth of living expenses saved, you won’t panic if there’s no immediate income.
I calculated my family’s basic expenses and saved enough cash to cover 12 months of living costs under strict budgeting. I also have other investment accounts, but those I treat as off-limits. For me, this emergency fund is crucial for emotional stability during anxious times.
Entrepreneurship isn’t about having projects every day or income every month. You need to honestly face your savings and spending, and plan your cash flow carefully.
Whenever I feel anxious, I open my budget spreadsheet to check savings and remind myself that my “lifeline money” is sufficient. Then I calculate the minimum I need to earn each month to keep my “health bar” from hitting zero, so both life and business can continue.
💡 Tip: Aim to save at least six months’ living expenses (excluding business costs). If you’re married or have children, this is even more important. Have open conversations with your partner about worst-case scenarios, such as whether one of you might need to return to work temporarily, or whether childcare budgets need revisiting. The sooner you clarify these, the less stress you’ll face.
3. Secure Your First Client (Preferably While Still Employed)
Starting to find clients only after quitting creates enormous pressure and puts you in a very passive position. Ideally, you want to lay the groundwork before you leave, building potential projects in advance.
I negotiated a short-term contract with my previous company so I had a stable income source on my first day out. That greatly reduced my stress. I also reached out to past clients to see if they had upcoming design needs — one happened to be starting a new project, so I was able to transition smoothly.
I actively chatted with friends and weak connections in other fields to explore cross-industry collaborations. For example, some software engineers needed designers, which opened new opportunities.
📎 Tip: Take initiative. Contact former colleagues, clients, or friends and let them know you’re starting freelancing or a studio. Ask if they have work or could introduce you to potential clients. This proactive approach is more reliable than waiting for work to come to you.
4. Build Your Trustworthiness
Clients often judge more than just your portfolio. They want to know if you’re trustworthy.
If you understand sales, you know the three essentials for closing a deal are: need, value, and trust.
Sometimes the client knows exactly what they need, and you happen to offer it, so the project naturally proceeds. More often, clients aren’t sure what they want. You can help by asking questions to clarify their real needs, guiding them through the process, and sharing your experience from a collaborative, win-win perspective.
Some clients are very clear on goals. They want to save time, reduce costs, or maximise impact. Others value whether you get along, how smooth communication is, and whether the chemistry works. For these clients, trust and rapport are the deciding factors.
You can start a blog, share professional insights, and tell case stories to showcase your expertise and working style. This will encourage referrals and justify reasonable pricing.
I have often shared articles , design notes and life observations , originally just for fun and to express myself. Writing is my natural outlet, and luckily, it has helped more people get to know me. When I first arrived in the UK, I also actively managed design communities to foster mutual support and growth. These accumulated experiences and relationships helped build trust and made it easier for future collaborators to find me.
🎯 Tip: The key is not to “sell yourself” aggressively, but to make people trust that you can deliver and are easy to work with.
5. Be Clear About What Projects You Will (and Won’t) Take
Initially, it’s tempting to say yes to everything, but over time, this can lead to burnout and a loss of focus. Set an “early-stage goal” — for example, only take branding and website design, or focus on MVP collaborations for digital products. This helps build reputation and streamline workflows faster.
Be clear about why you want each project — to gain local experience, build a portfolio, or develop a reputation. You might start with mutually beneficial pricing, which is common early on. Just be sure to clarify upfront that this isn’t your standard rate long-term.
For me, if my main clients are startups, I will naturally take on many all-in-one design projects. But my expertise remains software MVP design. If a project also involves web or branding, I collaborate with other designers so that each professional focus is in the right place.
✂️ Tip: List three types of projects you do not want to take (e.g. pure outsourcing, very low budget, poor communication). This helps set boundaries and avoid draining work.
Conclusion: Quitting Your Job to Start a Business Isn’t an Answer, It’s Another Challenge
Freelancing and entrepreneurship sound free, but the reality is tough. There are often no clear start or finish times . You might work every day, your mind never switches off.
Days without income are hard to swallow. Unlike working for a company, income is unstable. One month you might land a big project, the next you might earn nothing. So it’s important to plan your finances and cash flow early.
Instead of asking “Is now the right time to start a business?” ask yourself: “Am I willing to pay the price for this lifestyle?”
There’s no standard answer to this path, but thinking carefully about the points above will help you walk it more steadily.