Whenever someone asks me whether they should start their own business, I give them more or less the same answer: it depends on how much healthy madness you can handle. Because owning a business turns out to be a pretty strange mix of freedom, responsibility, uncertainty, and satisfaction that no manual ever explains. From the outside, it gets romanticized quite a bit: no boss, control over your schedule, working from wherever you want, and building something of your own. All of that can be true, but it’s only part of the story. When you own a business, much of the risk and many of the decisions that a traditional organization spreads across departments, supervisors, and entire management structures end up a lot closer to you. Sometimes literally in your lap. That’s why, after more than fifteen years of doing this, I’m increasingly convinced that entrepreneurship involves some sanity and a whole lot of madness.
The madness part
No one warns you enough about this part. Set hours don’t disappear necessarily because you’re working around the clock, but because responsibility doesn’t punch a time clock. Your business tags along in your head in the shower, in traffic, and every so often at three in the morning, when a solution hits you for something you’ve spent days trying to figure out. If something important goes wrong, there isn’t always another department to escalate the problem to. Eventually, someone has to make the call, and often that someone is you. Then there’s the financial risk, which is a lot less romantic than talking about entrepreneurship on social media. According to data from the U.S. Small Business Administration’s Office of Advocacy, between 1994 and 2020, approximately 48.9% of new business establishments with employees survived at least five years. Put another way, just over half didn’t make it that far. I’m not saying this to scare anyone, but because starting a business with your eyes open is very different from falling in love with nothing more than the idea of owning one. Behind the logo and the “we’re open” announcement come cash flow, collections, payroll, taxes, contracts, clients, good months, slow months, and decisions that don’t always have a perfect answer.
There’s also the emotional cost, which is harder to put on a chart because we don’t all experience entrepreneurship the same way. Research on self-employment reflects that very contradiction: you may have more autonomy, but you may also face greater time pressure, financial insecurity, and worries about stability. In Puerto Rico, that tension is particularly interesting. The Global Entrepreneurship Monitor reports fairly dynamic entrepreneurial activity, with around one in six adults starting or running a new business, but only about one in twenty running an established one. GEM itself describes that relationship as a sign of a dynamic but potentially fragile ecosystem. On top of that, among those who see good opportunities to start a business, a considerable share still say that fear of failure could stop them. To me, that says a lot. Here, we talk a lot about pushing forward and finding a way to make things work, something deeply rooted in who we are and that I value tremendously, but the uncertainty is still real. I’ve lived it. There are stretches when everything flows, and others when a business worry weighs more heavily than any campaign, project, or deadline.
The sanity part
And yet, here I am, more than fifteen years after founding Alterno in 2009. If it were all madness, probably no one would last very long. The other half of the equation is real too, and in my case, it carries a lot of weight. Creating something of your own lets you build a different relationship with work. That doesn’t mean you have absolute control, because you still answer to clients, employees, commitments, numbers, and deadlines. But you do have a much greater say in what kind of company you want to build, who you want to work with, and how you want to organize much of your life. For me, that autonomy has been one of the biggest reasons to keep going.
Owning a business lets me decide where I work, which clients I collaborate with, which projects I want to pursue, and even how to arrange my morning so I can get out for a bike ride before the day’s running around begins. That doesn’t mean every day is flexible or that you can just close your laptop whenever you want. There are weeks when it’s exactly the opposite. But the autonomy is real, and research on self-employment recognizes that paradox too: people who work for themselves tend to report greater control over the content and organization of their work, even when they may face more time pressure, uncertainty, or financial insecurity. For me, being able to make many of those decisions is enormously valuable. It doesn’t eliminate stress, but it changes your relationship with it because you know what you’re building for, and for whom.
Then there’s everything you learn. Owning a business forces you to become a kind of professional generalist. That doesn’t mean you become an expert in finance, contracts, human resources, sales, technology, operations, and marketing all at once. But you do learn enough about each to ask better questions and recognize when you need someone who knows more than you do. That hands-on education happens quickly because decisions have real consequences. But for me, there’s another dimension that matters even more: the business stops being just your idea and becomes a small social system. There are collaborators, clients, suppliers, families, relationships built on trust, and people who depend on things being done right. Seeing something that started as a conversation and an idea in Caguas grow into projects, work for Puerto Rican talent, and solutions for real clients changes how you understand what it means to own a company. That doesn’t show up the same way on a financial statement, but it’s part of the value too.
My verdict
Sanity or madness? A little of both. What I wouldn’t do is romanticize either one. Sometimes the conversation around entrepreneurship boils everything down to discipline, sacrifice, and drive, as if the people who succeed simply worked harder, and the people whose businesses didn’t work out just didn’t want it badly enough. Reality is a lot more complicated. Access to capital, the market, business education, public policy, support networks, family, the economic climate, and even luck all matter. Studies of entrepreneurship in Puerto Rico continue to point to challenges in areas such as financing, public policy, and early-stage business education. That doesn’t mean individual effort doesn’t matter. Of course it does. But working twelve hours instead of eight doesn’t solve everything either. For me, the sane part lies in the autonomy, the learning, the chance to create something, and the impact you can have. The crazy part is accepting that all of it comes with uncertainty. The full package is much less perfect than the entrepreneurship brochure makes it look, but it’s also a lot more interesting.
If you’re thinking about taking the leap, my advice is still pretty simple: go in with your eyes open. Run conservative numbers, understand how much you really need to operate, try to build a support network, and don’t confuse being busy all the time with making progress. Owning a business isn’t a superior way of life or a medal everyone needs to chase, either. Some people are much happier and more effective building a career within an organization, and that’s perfectly fine. But if you’re already here, if you chose this path and you’re having one of those days when everything seems to get complicated at once, remember that some of that madness comes precisely from caring about what you’re building. After all these years, at least in my case, I still think the sanity makes up for the madness. Most days.
References
U.S. Small Business Administration, Office of Advocacy. Frequently Asked Questions About Small Business, March 2023. The publication reports that, among new business establishments with employees observed between 1994 and 2020, 67.7% survived at least two years, 48.9% at least five years, and 33.7% at least ten years. advocacy.sba.gov.
Global Entrepreneurship Monitor (GEM). Entrepreneurship in Puerto Rico, 2025 Entrepreneurial Activity Review. The latest profile of Puerto Rico covering entrepreneurial activity, perceptions of opportunity, fear of failure, and conditions in the entrepreneurial ecosystem. gemconsortium.org.
OECD. Brieger, S., Kruse, S. and Potter, J. The Job Quality of Self-Employment in Europe: A Longitudinal Perspective, OECD SME and Entrepreneurship Papers, No. 73, 2025. The study examines autonomy, time pressure, job security, financial well-being, and other dimensions of the self-employment experience compared with salaried employment. oecd.org.
