Taking a leap of faith, especially in entrepreneurship, is daunting because it means leaving behind the security of a steady paycheck and benefits to pursue your business dreams. This journey can be terrifying as you’re responsible for every outcome, and failure becomes a very public affair. The higher your educational background, the greater the risk, considering what you’re potentially giving up. However, the rewards of entrepreneurship can be immensely satisfying, surpassing any promotion or salary raise.
I’ve been on this entrepreneurial path since 2009 when I launched Financial Samurai. Initially, the site only made about $250 in its first year. My primary aim wasn’t financial—it was more about having a creative outlet during the global financial crisis. Despite the challenges and the initial low income, any small earnings felt significant due to my minimal expectations.
Over time, the site grew enough to support a family of four in San Francisco, though it wasn’t without its nerve-wracking moments. For instance, my Series 7 license was set to expire two years after I left my day job. Facing the daunting prospect of retaking this difficult exam, I was highly motivated to make Financial Samurai work. During those two years, I published consistently and saw positive growth, but I kept my options open by interviewing at financial firms. Despite these fallbacks, nothing excited me as much as my own venture. Eventually, I let the license expire, which forced me to commit fully to Financial Samurai.
For anyone considering entrepreneurship, I recommend setting a realistic time limit to evaluate your business’s viability, like three years. If your venture isn’t showing promise within that period, it might be wise to pivot or re-enter the workforce. This timeframe provides a good balance to test your idea without risking too much career stagnation.
If Financial Samurai hadn’t succeeded, I had several plans. I could have returned to investment banking, possibly at a boutique bank to reduce the hours and stress. Alternatively, moving to Honolulu was an appealing backup for a more relaxed lifestyle, supported by a modest online income and my savings. Another scenario involved entering the fintech sector, leveraging my experience to consult and eventually applying those insights back to my blog.
Through all these potential outcomes, the consistent theme was my commitment to Financial Samurai as a creative and financial endeavor. I’ve learned that having a clear cutoff, like my license expiration, can decisively push you toward full commitment to your entrepreneurial goals.
For those considering a leap into entrepreneurship, here’s my advice:
1. Start your business as a side hustle while maintaining your day job. This reduces financial pressure and allows you to test your business idea without immediate risks.
2. Secure financing options like refinancing your mortgage or securing a line of credit before quitting your job, as it’s harder to get loans without steady W2 income.
3. Ensure you have a financial cushion, ideally one that covers at least two years of living expenses, or a severance package that can support you as you grow your business.
4. Learn continuously from both successes and failures in your field, and build a network of contacts who can provide support and advice.
5. Discuss your plans thoroughly with your spouse or partner, especially if one of you will continue in a stable job. This dual approach can provide emotional and financial balance as you navigate the uncertainties of entrepreneurship.
Finally, embracing entrepreneurship is about balancing risk with potential reward. It’s about accepting the possibility of failure but also recognizing the personal growth and opportunities that come from pursuing what you truly enjoy. Whether Financial Samurai succeeded or failed, my commitment to carving my own path was the true reward, offering a fulfilling venture that aligned with my personal and financial goals.
