Swapping “founder” for “employee” might sound like a step backwards, but for many, it’s a strategic and exciting next chapter.
As a career coach specializing in tech executives, I’m often approached by entrepreneurs who are contemplating a return to the corporate world after years of running their own businesses.
If you’re wondering whether it’s time to re-enter the 9-to-5 world, you’re far from alone. In fact, some of my most successful clients have made this very move (and absolutely loved it!).
In this article, I break down:
- How to decide whether returning to corporate is the right move for you
- The potential benefits and drawbacks of being an employee versus an entrepreneur
- Proven tips and strategies for successfully transitioning from entrepreneur to employee, drawn from the real-life wins of my clients
Should I Work For Myself Or Go Back To Corporate?
Ultimately, only you can make this call. That said, here are some questions to help guide your decision:
- What’s driving your desire to return to corporate?
- Are you energized or drained by the day-to-day of running your business?
- How much structure (or freedom) do you want in your next chapter?
- Do you miss being part of a larger team?
- Are you looking for more financial stability, benefits, or work-life balance?
- What does success look like for you in this next chapter of your career?
Try journaling your answers or talking them through with a trusted advisor or coach to uncover new insights.
What Are The Benefits Of Being A Corporate Employee Versus An Entrepreneur?
While entrepreneurship offers autonomy and creative freedom, corporate roles come with their own advantages:
Better work-life balance
Many founders return to in-house roles for a more sustainable lifestyle. While “balance” looks different for everyone, many clients who have made the transition share that it’s easier to mentally “check out” as an employee than when they were a founder.
One client, who previously ran a boutique marketing agency, shared that he was finally able to take his first real vacation after joining a mid-sized tech company. He got to spend time with family without Slack pings or surprise client emails. Being able to spend this uninterrupted time with his family was truly life-changing.
Less stress
As an employer, you’re no longer the one responsible for everything. As part of a team, you get to focus on your Zone of Genius instead of constantly switching hats. Clients often share that being a corporate executive is stressful, but less so than being a founder.
A former startup founder shared that she still works incredibly hard but sleeps much better knowing that payroll isn’t her problem and that she’ll always have a paycheck in her account.
Increased pay and benefits
Depending on your business’s size and profitability, a corporate role can provide competitive compensation, stock, equity, and health benefits that can be difficult to attain as a founder.
The previously mentioned startup founder not only increased her salary but also gained access to healthcare, parental leave, and equity. All of these were things she hadn’t prioritized while bootstrapping her startup but were now important since she was starting a family.
Improved stability
While the tech industry has had its ups and downs, especially recently with mass layoffs, many entrepreneurs are happy to find more predictable income and growth opportunities in corporate roles.
A client who was an early employee at two e-commerce startups shared how nice it was to receive regular paychecks that weren’t dependent on that week’s online sales.
What Are The Difficulties In Moving From Entrepreneur To Employee?
The transition to in-house isn’t without difficulties. Common challenges include:
Bureaucracy and red tape
From lengthy interview processes to slower decision-making, navigating corporate bureaucracy can be a shock after years of being your own boss. Even innovative tech companies have internal processes and politics that can quickly become frustrating.
One of my clients, a former SaaS founder, shared how surprising it was for him to need multiple approvals to send out a customer email. This was something he used to do in a matter of minutes. It wasn’t that the processes were bad, per se, just different. Over time, he learned how to work within the current system while still leveraging his entrepreneurial mindset to drive innovation and influence change from the inside.
Less direct impact
Some clients share that they feel like “just another cog in the wheel” once they return to a team. If impact and ownership are high priorities for you, be intentional about the companies and roles you target.
One client, who had previously led a fast-growing startup, moved into a senior product role at a large enterprise company. The salary and benefits were great, but she quickly realized she missed the sense of ownership she had as a founder. We worked together to shift her internal narrative from feeling “small” in a big organization to recognizing where she could drive major influence within her team, advocate for the needs of her customers, and champion meaningful initiatives for her departments. While it wasn’t the same as running her own company, she was able to find a greater sense of purpose in her new role.
Identity shift
Stepping out of the “founder” role can bring up unexpected emotions and feelings. After years of being the final decision-maker, it can feel disorienting (and sometimes even humbling) to shift into a role where you’re reporting to someone else.
Clients have shared that they sometimes struggle with feeling “less important” or worry that they’re giving up a piece of their identity as an employee. This isn’t uncommon, and it doesn’t mean you made the wrong choice; it just means you’re human.
Please remember that your title doesn’t define your value. The experience, skills, perspective, and resilience you bring as a founder are incredibly valuable and sought after in many corporate environments.
How Do I Go From Entrepreneur To Employee?
Like launching a startup, transitioning to corporate takes strategy. Here are five practical steps you can take to make your transition as smooth as possible:
1. Get clear on what you want.
Begin by reflecting on what you want in your next role. Some questions worth asking yourself as you transition include:
- What size companies am I targeting? (Startup, mid-size, or enterprise?)
- Do I want to be in a leadership role, or am I open to stepping back into a managerial role?
- What kind of impact do I want to have?
- What industries energize me right now?
- What does my ideal compensation package include?
- How do I want to spend my time day-to-day?
Getting clear on what you want in your next chapter will help you target the right roles and inform your job search efforts.
2. Target appropriate roles.
As you conduct this reflection, identify roles that make sense based on your background, experience, and skills. For instance:
- Would you thrive in a more generalist role such as a General Manager, Chief Operating Officer, or Chief of Staff?
- Or are you better suited for a more specialized role, such as product, engineering, or human resources?
Keep in mind that the titles and scopes will look different based on the industry and the size of the company.
Unless you led hundreds or thousands of employees, landing a vice president or C-suite role at a Fortune 500 tech company might not be realistic right out of the gate.
3. Identify and communicate your transferable skills.
As a founder, you likely wore lots of hats and amassed tons of transferable skills, but this doesn’t mean you need to include them all on your resume or mention each one in interviews. Focus on what’s relevant to the role you’re targeting.
Think of your resume like baking a cake: you wouldn’t throw bacon into a cake just because it was in your fridge.
Tailor your story. If you’re eyeing a head of product role, emphasize your experience scaling roadmaps, leading agile teams, and shipping features rather than your fundraising wins.
[Read: How To Write A Career Change Resume (With Examples)]
4. Communicate your unique value proposition.
In the same vein, communicate what sets you apart. This is what I call your fabulousness.
You want to highlight your entrepreneurial chops without making potential employers ask, “Are they really ready to be an employee again?”
Frame your entrepreneurial experience as an asset. For example, “I bring a founder’s mindset and a consultative approach to problem-solving, which is perfect for a company navigating hyper-growth.”
5. Leverage your network.
Don’t underestimate the power of your existing network and connections when seeking a corporate gig. Tap your former clients, vendors, collaborators, and industry peers.
Clients often worry that this will make it look as if their business wasn’t a success or is struggling. However, so long as you communicate why you’re looking to make the transition from entrepreneur to employee, you won’t raise any flags.
Your reason can be as simple as, “I miss being a part of a team, and I’m exploring in-house opportunities where I can contribute at a larger scale.”
Final Thoughts
Whether you’re craving more stability, want additional work-life balance, or miss being part of a team, transitioning from entrepreneur to employee is possible, so long as you are intentional about the companies and roles you’re targeting and have the right strategy.
If you need support with your journey, please reach out or schedule a consultation. I’m here for you! You’ve got this!
