You are an entrepreneur who came up with an amazing solution to a real consumer problem. You have launched a company and you have beaten the odds: 90 percent of all startups fail within their first five years.
I’m a deeply fortunate entrepreneur. Ladders, the first company I co-founded, was in that 10 percent of success stories. Our company addressed a real need in the employment search space and its interface and ease of use on all sides of the hiring experience resonated with the right people. As CEO, I saw it grow past that key five-year landmark and continue to thrive. But then I stayed too long.
5 Critical Questions for Founders to Ask Themselves
- How am I doing?
- How is my business doing?
- Am I still the right person for the moment?
- Why do I want to stay?
- What do I want to do next?
Leaving a business you build from the ground up is personally and professionally challenging – you’ve invested your whole self in it. By the time you see real success, it’s encoded into your DNA. Entrepreneurs also possess certain personality traits that make it challenging for us to quit anything: We have a never-say-die commitment to seeing things through. We have a resonant passion for what we’re building. We have a preternatural ability to seek solutions and workarounds.
And that’s how, 11 years after its founding, I was leading a company that was no longer the right fit for me — and vice versa. My professional growth was stagnant and I was watching my business’ success plateau. When I took a hard look at where I was and separated myself from the entrepreneurial tendency to hang on and dig in deeper, I knew that I was ready to move on. I realized these were the questions I should have been considering.
How Am I Doing?
When you take a step back from the work you’re doing, ask yourself, Am I coasting along? Am I growing? Am I excited? As terrifying as it sounds, failing fast is a gift and stagnation is a curse. After crossing the five-year threshold, take time each year, maybe twice a year or quarterly, to ask yourself these questions. Vibes are a good compass; after all, your gut instinct got you here. Eleven years into founding and leading Ladders, I realized that the energy felt off, and I was disconnected from the now-third generation of colleagues who had new ideas.
How Is My Business Doing?
Is the business heading in the right direction? Are you meeting the KPIs you’ve established for yourself and others? If you’re not meeting those benchmarks, consider the possibility that you’re losing the critical fire in your belly. A cold, hard fact toward the end of my tenure at Ladders was that we were no longer growing as a company. To continue to thrive, the business needed fresh leadership and it was time for me to depart.
Am I Still the Right Person for the Moment?
You are likely an outstanding leader, but are you the right leader for where the business is right now? Have you reached a point where the solution you’re providing has moved into territory that is not interesting to you, or does not play to your strengths?
Five years into co-founding and running Ollie, a dog-first company providing fresh, healthful food for dogs of all ages, breeds and sizes, the business had evolved from addressing pet care, an area of deep passion for me, to addressing supply-chain solutions. We’d solved the initial problem, and the new problems we were solving were not my area of expertise. Admittedly, I was not interested in developing this area of expertise. Once I came to terms with this, I knew that the business needed a leader who was invested and interested in those issues.
Why Do I Want to Stay?
Give an honest assessment of your current feelings around work. Are you enthusiastic about the growth? Are you fulfilled by building something and seeing it progress? Do you get out of bed in the morning excited to address the day’s challenges? Or are you staying because you think you have to?
We all have days where we need to do tasks that we’re not excited about, so this question requires more examination than looking at isolated incidents, or letting one disappointing day dictate your future. But if you are uninspired, and it starts to feel like you’re no longer inspiring the people around you, it might be a good time to pass the baton.
What’s Holding Me Back?
Sometimes, even if a situation isn’t working, it feels easier to stick with what you know rather than launch yourself into something new. When you’ve achieved something as significant as building a business that has survived growing pains, it’s easy to take on an imposter syndrome attitude as you consider what’s next and wonder, Was I good or was I lucky? If you experience the champagne problem of success right out of the gate, it’s difficult to consider starting from scratch, knowing the odds, challenges and struggles you face.
But you should also consider that you might not be giving yourself enough credit. You were successful once, why wouldn’t you be successful again? Similarly, if you have a track record of resilience, there’s no reason to doubt that you’d be any different this next time around.
Who Will I Be Without My Company?
When you’ve given a business your all, it can be difficult to conceive of who you are without it. So ask yourself, Who am I? When I was preparing to depart Ladders, I realized that in addition to being a founder and CEO, I was a dog lover. I was deeply enthusiastic about nutrition and fitness. I was and still am more than the pre-packaged identity in my corporate website bio. Detach yourself from the notion that a company founder is all you are or all you’ll ever be.
What Do I Want to Do Next?
Starting a new company might not be what you want. And that’s okay. Once you explore who you are and who you want to be, you can choose an unprescribed path.
Did you love aspects of scaling your business? Another founder might benefit greatly from your contributions as a CEO, president or advisor. Are you passionate about mentoring staffers and helping them realize their goals? Maybe you want to take a turn at teaching business fundamentals. Are you interested in helping another business grow? Maybe you want to consider using some of your exit package or equity to invest in other entrepreneurs’ visions.
My experience leaving my second startup, Ollie, was far less painful than leaving my first. I was mindful of where the business was, where I was, and where those two paths were no longer aligned. While most of my founding team was still in place, I negotiated the opportunity to continue on as an advisor and board member, and I was part of the process of hiring the next CEO.
If there’s one takeaway I could leave with other entrepreneurs wrestling with, it would be to challenge the notion that moving on means giving up. Moving on doesn’t have to mean giving up. It could be a final act of love and passion for the business you created and a recognition that you need to entrust it to others so it can become the greatest it can be.
On the flip side, you can also think about it as an act of self-love. If your current situation no longer helps you professionally and personally flourish, don’t be the one to hold yourself back. Be the one brave enough to explore what’s next.
