I just completed an 1,800 mile road trip on Route 66 from Oklahoma City to Santa Monica Pier, while reading Steinbeck’s ‘The Grapes of Wrath.’ 2026 is the centennial anniversary of Route 66, also known as the Mother Road. It begins in Chicago and stretches south and west through Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and finally California. Commissioned in 1926 as one of the first U.S. Highways, but not fully paved until 1938. It was originally a wagon trail, but during the depression and dustbowl it became the primary route for migrants forced off their farms, and seeking a better life in California. Their farms and businesses had been foreclosed, and they had to move off their land and sell nearly everything in order finance their journey and eat. Migration was a necessity, but based upon the promise of work and a new life in California, they were optimistic.
Over the last few years, I have been involved in mentoring start-up entrepreneurs. While their situations are nowhere near that of the dustbowl migrants, I was struck by the parallels. Many individuals have lost their jobs and are facing a challenging job market. Some are stuck in jobs that are not fulfilling or intolerable. They all feel the necessity to move on, but the entrepreneurs are driven by an optimism that tells them they can make their own success. Like the dustbowl migrants, the odds are certainly against them. By some studies, 20% of tech startups fail in the first year and 70% in the second year. Over 40% fail because there is a lack of market need for their offerings, while nearly 30% run out of funding before they become self-sufficient. Despite these dire statistics, like the dustbowl migrants, the necessity to move on drives the optimism that spurs these entrepreneurs to take the risk. Bravo!
When someone loses their job, it can feel like they have been kicked out of the nest, and their choice is to fly or fall. Some dabble in entrepreneurship while they frantically look for a new job. For then, starting a venture feels like a necessity, but it is paired with fear, and not optimism. While failure does not feel like an option, they are not confident in success, and in fact it seems out of reach. For these entrepreneurs, the lack of commitment, and their hesitancy almost certainly dooms their endeavor to failure. Others see their job loss as a sign that the universe is telling them it is time to pursue their dream. The necessity to earn a living gives rise to the optimism that their great idea is the path to success.
The most challenging group are the currently employed dreamers who want to start a business, but are unwilling to let go of their steady paycheck. They have a great idea, but are staring into the abyss of a startup with a high probability of failure, and like Tarzan swinging from vine to vine in the jungle, they will have to let go of the current vine and trust that the next vine will hold their weight. That fear of letting go is holding them back from fulfilling their entrepreneurial dream. When I work with one of these entrepreneurs, to get them over the hump, I often find I am trying to help them paint a future picture by asking open-ended questions such as: Imagine what launching the venture will feel like and the first 180 days? What goals and checkpoints would you set so that you know it is working? How much cushion do you really need to have the comfort to let go of your current job? I often remind them that they are smart and have great skills, and even if it fails, they will still be valuable and employable. The toughest question is how will you feel if you never try?
I focus on helping the entrepreneur to build a conservative and comprehensive financial model of the business, while at the same time constantly guiding them to be very specific about what they are bringing to the market and why someone will pay them for it. Entrepreneurs are creative people, and they bubble with big ideas. A startup requires a big enough idea to build a sustainable business, but narrow enough that the business can have laser focus on what needs to be done to succeed. There is generally not a lot of time or runway to experiment with too many ideas, so the path needs to be clear at the start, but it has to have enough flexibility to be responsive to early market feedback.
Necessity is the mother of invention, and for entrepreneurs it can also be the mother of optimism. No matter how the necessity was manifest, and even in the face of frightening odds, committed entrepreneurs demonstrate their optimism every day.