Making the jump from a corporate career to entrepreneurship can be exciting and a bit scary. You’re used to structure and clear paths, but now you’re building something of your own. It’s a whole new world with different challenges and rewards. So, what can you do to make this transition smoother?

Starting your own business means taking more risks and making a lot of decisions on your own. The shift can be overwhelming, but with the right mindset and approach, you’ll be able to navigate this change successfully. Let’s dive into what can help you most as you make this leap.

21 Tips for Transitioning from Corporate to Entrepreneurship

1. Prepare for Both Successes and Failures Ahead

Be prepared for the ups and downs. You will have successes and failures. This is part of growing and figuring it out. Fail fast; push past the fear of whether you will succeed. Entrepreneurship is a roller coaster.

In the low moments, remember you are not alone. Talk to people, share, be vulnerable. Find your tribe of people who support you. Every time I share and put myself out there, I always get a brilliant idea to try in return for the vulnerability. You also don’t know how much your story might inspire or help someone else. 

Rachel Johnson, Fractional Marketing Executive and Growth Scaler

2. Pace Yourself and Focus on Challenges

When transitioning to entrepreneurship from a corporate career, pace yourself and focus on challenges rather than just dreaming big. One of my favorite reads is “Outliers” by Malcolm Gladwell, where he talks about the 10,000-hour rule to master a skill. This concept applies to entrepreneurship too. For example, working 10 hours a day for 360 days a year sums up to roughly three years. If you give up before then, you might not have given it a real shot. Even as a type-A personality, I thought I could speed through to success, but I learned that rushing can actually sap your energy.

From my experience, while some people get caught up chasing dreams, I find it more practical to tackle challenges. Dreams often lead to disappointment when obstacles pop up, but viewing these as challenges can turn every hurdle into a step closer to success. Entrepreneurship is all about overcoming these challenges, so it’s crucial to prepare yourself mentally to keep pushing forward.

Alex LaDouceur, Co-Founder, Webineering

3. Own Every Success and Every Failure

Be prepared to assume the burden of responsibility for everything you do from here on out. This is not a bad thing. You will be responsible for the failures, sure, but you will also be responsible for the successes. Saying, “It’s not my job,” will no longer work. As soon as you enter the ring of entrepreneurship, the buck stops with you. Treat that responsibility with respect. 

Logan Burchett, Co-Founder, Forecastr

4. Prepare for Financial Ups-and-Downs

Switching from a corporate job to entrepreneurship means getting ready for some money ups-and-downs. When you run your own business, you can’t count on a regular paycheck like you did before. Some months you might do really well, but others could be tough. It often takes longer than you’d think to start making money, which can catch many new business owners off guard. 

To handle this, it’s smart to save up some money before you start. Try to put aside enough to cover your bills for at least a year. This saved-up cash acts like a safety net. It helps you stay calm when money’s tight and lets you make smart choices for your business’s future instead of just trying to get by. Having this extra money saved gives you breathing room to build your business the right way, even when things get bumpy.

David Primrose, President, Metal Marker

5. Manage Peaks and Valleys Without Losing Balance

Brace yourself. Pace yourself.

The #1 advice I would give to those founding a company, coming from a corporate background is to prepare for the breakneck, all-out blitz pace of life in a startup. It’s peaks and valleys, all the time, it never stops, it’s so hard to stay in balance, and keep up.

There is no way to understand the fast pace of life running a company until you try it for yourself, but just know the pace will be lightning. Prepare for that, and don’t let it break you. Don’t give up, but also don’t fall prey to the pace and let the startup dominate everything else in your life. It will consume your life if you let it. 

Steven Plappert, Co-Founder & CEO, Forecastr

6. Learn to Wear Multiple Hats

Learn to wear multiple hats! Expect to take on various roles and responsibilities, especially in the early stages of your entrepreneurial journey. This might mean managing finances one day and leading marketing efforts the next. To handle these diverse tasks, prioritize your workload and use time-management strategies to ensure you’re focusing on what matters most. 

Recognize when it’s time to delegate or seek outside help, especially for tasks that are outside your expertise. Embracing this multifaceted role will help you build a well-rounded skill set and keep your business moving forward.

Albert Kim, VP of Talent, Checkr

7. Navigate Uncertainty, Embrace New Challenges

The differences between corporate and entrepreneurial work reveal themselves at different rates.  I’d suggest you find other examples in your experience (life) that created significant change and required shifting your behaviors and your mindset.  

Moving cities comes to mind.  All the landmarks, the “known paths”, are replaced with new unknowns.  Exciting things like new coffee shops show up, but so does the challenges of finding new friends.

Begin by recognizing the discomfort of not knowing the next step or next thing.  Embrace the exploration and try not to miss the efficiency you may have had.

Justin Fite, Co-Founder, Empiric

8. Validate Your Business Idea

Validating a new business idea is essential before taking the plunge. Market research and small-scale trials are key to this process. One should begin by defining who their ideal customers are and soliciting feedback on their concept, using methods like surveys, focus groups, or one-on-one interviews. This provides insight into whether there is an authentic demand for your product/service in the market. 

Launching with a minimum viable product (MVP) gives you real-world data points that allow further refinement of your initial idea while minimizing risk factors associated with larger-scale launches.

Jason Marshall, CMO & Executive P&L leader, Huntress

9. Build a Support Network for Entrepreneurial Success

Entrepreneurship may seem sexy …. but every founder will tell you it is an emotional rollercoaster ride.  You will experience the highest of highs and the lowest of lows – sometimes in the same week (or day).  It can also be really lonely as a founder / entrepreneur.  Make sure you have a solid support group.  Often this will be other founders, who understand what it is like.  Having a solid co-founder and/or co-founding team can be super helpful as you tackle challenges together and have others around you to celebrate the wins.  Embrace it as a journey, but don’t travel it alone.

Jeff Erickson, Strategic Partnerships, Forecastr

10. Master Your Mindset

When transitioning to entrepreneurship from a corporate career, it really begins with winning the inner game and mastering your mindset. Being an entrepreneur is tough, almost like being an elite athlete or an artist. You have to tap into deep reserves of courage, strength, intelligence, tenacity, will, resilience, and grit to build something significant or reach a goal.

What I’m saying is that life as an employee often revolves around fear—fear of losing your job, losing respect, or making mistakes. Many are also scared to leave their jobs and chase their dreams because they fear stepping out of their comfort zones.

As an entrepreneur, you operate without a safety net, which is terrifying but also exhilarating. You might be scared to push your boat into turbulent waters, but with perseverance, good planning, and a bit of luck, you might just find treasure. You need to focus on what you can do, start doing it, and stop worrying about what could go wrong.

If you’re worried, think it through and find a solution. If the fear persists, it’s probably just in your head. Recognize that and keep pushing forward. Once you gain momentum and things start rolling, the thrill of entrepreneurship will fuel your drive to succeed.

Anders Bill, Cofounder/CPO, Superfiliate

11. Leverage Experience Wisely; Avoid Overloading Your Team

Do a bit of self-reflection on what corporate experience is going to make the most impact in the short-term for your new team and start with those. It’s tempting to leverage all your experience of working in a corporate gig but you don’t want to overload yourself, or your new teammates, by bringing all the solutions. Speak from experience and know when to listen to ideas instead of keep presenting solutions.  

Casey Bolsega, Sr. Portfolio Manager, Intrepid Finance & Venture

12. Leverage Corporate Experience

You can use your corporate experience. We are made to believe that moving from a corporate career to entrepreneurship means starting over. The reality is that you have experience that you can transfer to your new business. Therefore, find a way to apply your current knowledge to your venture. Before I started my business, I was willing to throw my experience down the drain because of my bruised ego. I thought starting my own business was supposed to be my new start, a clean slate. However, transferring what I learned helped me move my business further and much faster.

Tanya Slyvkin, Founder & CEO, Whitepage

13. Be Authentic: You Don’t Need to Fit In

Be true to your authentic self. As an employee, you’re constantly working to integrate into existing teams and cultures; you’re naturally part of a bigger whole, and as a result you’re perpetually finding a way to work within the boundaries and constraints. Looking at it another way, you’re always fine-tuning your persona to work within the culture. As an entrepreneur, you’re o longer required to fit in or adapt. One of the best pieces of advice I got early on — from a CEO friend — was to simply be authentically me, even during the sales process. No longer do you need to play a persona; you can now just be yourself!

Joseph Loria, Founder and CEO, RetentionCX

14. Start Slow and Stay Small

As someone who transitioned from corporate marketing to running my own agency, my advice would be: start slow and stay small. It’s easy to feel pressure to scale quickly, but growing too fast can kill a young business. 

Focus on a niche, build a great reputation, and grow through referrals. Don’t be afraid to say no and be selective with clients. Find those who share your values and respect your work. The wrong clients will drain your motivation. 

Surround yourself with smart people. No one can do it alone. Contract out or hire help for skills you lack. I started as a solo freelancer but now lead a team. Together, we built a sustainable business. 

Continuously improve and adapt. Large companies move slowly, but startups must change fast. Try new strategies and partnerships. If something’s not working, fix it. Never stop learning and always exceed client expectations. Your reputation and business depend on it.

Jay Owen, CEO, Business Builders

15. Ensure Your Product Solves a Real Market Problem

Do the hard research to know your product or service is something the market wants. Know the problem you are solving, and know if people are willing to pay you to solve that problem. 

Lloyd Easters, Integrator/Chief Investment Officer, Invst

16. Cultivate a Strong Personal Network

One crucial piece of advice for someone transitioning to entrepreneurship from a corporate career is to cultivate a strong personal network. In the corporate world, you often have established connections that can provide support, advice, and opportunities.

As an entrepreneur, these relationships become even more vital. Actively engage in networking events, join industry-specific groups, and leverage social media platforms like LinkedIn to expand your reach.

Building a community of mentors, peers, and potential collaborators can offer invaluable insights and open doors that may lead to partnerships or funding, helping to ease the transition and accelerate your business growth.

Amit Doshi, Founder & CEO, MyTurn

17. Build an MVP Before Committing Fully

If at all possible, start as a side-hustle until you’ve proven something. For example: build your MVP nights/weekends and then get real, paying customers (ideal) or some other tangible results. We did this while also bootstrapping PureInsights, which has kept 100% equity with the founders, even as we have grown revenue, profits and our team over the past 8 years. While 2 of the 3 co-founders of PureInsights had been independent consultants, none of us had ever launched a tech company.

Of course side-hustle and bootstrapped isn’t a one-size fits all. If it’s not possible for your idea, get to MVP and start selling your stuff just as soon as you’re able to. There are countless examples of iteration without revenue or tangible results until resources ran out. I won’t rehash them here except to say don’t become another one by focusing internally for too long.

Rick McGlinchey, Co-Founder, PureInsights

18. Keep Your Day Job Initially

Think twice about quitting your day job right away. It might be tempting to dive headfirst into your new business, but trust me, there’s a lot to be said for keeping a steady income while you get your feet wet.

Imagine it like training wheels. Your current job can be your safety net. You can test out your business ideas, learn new skills, and build up your savings without feeling the full pressure of making it work from day one. It’s like a warm-up before the big game—it gives you time to practice and improve.

Tarek El Ali, Founder, Smart Insurance Agents

19. Adopt a Fresh Mindset for New Ventures

Release the need to reuse past playbooks.  Just because a strategy or tactic was effective in an enterprise context does not mean that same strategy or tactic will be effective in entrepreneurship.  The contexts are fundamentally different.  In enterprises, you largely execute.  In entrepreneurship, you largely create.  Enter with a beginner’s mind, ready to discover what works now and who you need to be now to succeed as a leader. 

Karen Mangia, President & Chief Strategy Officer, The Engineered Innovation Group

20. Discover Strengths and Learn from Entrepreneurial Experiences

Taking the leap into entrepreneurship is more than starting a business—it’s a journey of self-discovery.

As you navigate this path, you’ll uncover your strengths, learn how to make critical decisions under pressure, and connect with like-minded visionaries. Embrace the journey, learn from every experience, and you’ll find it not only challenging but incredibly rewarding.

Eric Marshall, Founder, Agent700 

21. Stay Flexible While Pursuing Your Entrepreneurial Vision

Transitioning from a corporate job to entrepreneurship should start with a clear vision. Define your goals and make sure you understand your market enough to identify true opportunities. Visualize what success might look like in the short, medium, and long term. Then set achievable milestones and communicate your vision to inspire support. Your daily actions should align with this vision and remain flexible to adapt to changes.

Matt Hunckler, CEO, Powderkeg  

Conclusion:

Transitioning from a corporate role to entrepreneurship isn’t easy, but having a clear piece of advice to guide you can make a big difference. Focus on staying flexible and embracing the unknown while leaning on your past experiences. With patience and persistence, you’ll find your way in this new journey.