Prospective searchers often ask me, “Was it worth it?” They want to know if my decision to leave a great career, move back to my hometown, and buy a small business was worth it. It’s a tough, tough question to answer. What most searchers are really asking me is, “Was it worth it financially?” I mean, no, not in a vacuum. I would have made an order of magnitude more money if I had stayed in private equity for the past 4+ years. My equity in Blooma Tree isn’t worth enough to offset that either, and it likely never will be. That said, I can pay myself enough to cover my life costs. I’m not saving money, but I’m not losing money either. Many of my peers spent the last couple years in business school to the tune of a couple hundred thousand dollars between tuition & life expenses. Based on that, this life path was a cheaper way to learn a lot more, and still have the potential of a good financial outcome in the years to come. But that’s not a whole answer. ---------------------------------------------------------------------------- Other searchers are implicitly asking, “Was it worth it from a lifestyle perspective?” I mean…kind of? In many ways, this is a harder job than working in finance. Not in hours — I work fewer hours for sure. I work more flexible hours as well. But the emotional & energetic output required of me on a weekly basis is higher than anything I did in finance. So yes, my lifestyle is better in many ways — I have more control over my time. I can go home early if I need to help around the house. I can trade a couple hours of hanging with my friend’s baby in the middle of the day for a couple hours of work in the evening. I’m a better partner to my girlfriend and a better friend to my core people. I can dedicate proper focus to them when it’s time to focus on them. I can choose to deprioritize an initiative in the business for a bit if my people need me to prioritize them. I can choose to have some weeks be “maintenance” weeks in the business, while others are “drive the business forward” weeks. But also no — I have a seemingly-permanent form of low-grade business owner anxiety. I check our business bank account daily, partially out of habit, partially due to catastrophic thinking. I check our newly closed sales figures on an hourly basis (the downside of a working digital CRM is I can actually see that instantly on my phone). I’m always one bad phone call away from my day or week being truly blown up. Not in a finance way, which was more like “cancel your dinner plans and come to the office for the next 3 days.” The calls I’m talking about are “a truck crashed into a house.” That kind of phone call happens with less frequency these days (knock on wood), but it can still happen. I didn’t suffer from these forms of work-induced anxiety in finance (though I suffered from many others that have since dissipated). I was confident & secure in my work in a way that I don’t anticipate ever feeling as a small business owner. Still…not a complete answer. ---------------------------------------------------------------------------- Others are asking, “Was it worth it professionally?” Thankfully, this iteration of the question can be answered with a resounding yes. That said, that’s somewhat due to the fact that the skills attained in finance are fairly specific and non-transferable, so I was in many ways starting from scratch. My job in private equity was prestigious and well-paid, but the skills developed were less applicable to running a small business than those developed as a: - shift manager in a restaurant - stay-at-home parent/household manager - platoon leader in the military - retail store general manager (or assistant manager) - high school teacher - captain of a competitive sports team The #1 role of a small business owner is to lead people. This includes hiring well & firing responsibly. It involves holding the team accountable and having standards. It’s giving difficult feedback. It’s creating systems & processes that the team can actually replicate successfully. It’s giving them the tools, training, and vision for how to do their jobs well. I spent about 2 years being a D- manager — I won’t give myself an F, simply because we have retained some of our best people from my first couple years (thanks for sticking it out, team). I then spent 2 years learning to become a C+ manager — good enough to get by, but certainly not someone who should be writing blog posts about how to be a manager (most of my people management-related posts are inspired by me messing up and then sharing lessons learned). Launching the lifelong journey of being a good people manager has been a professional privilege. The reward of seeing an employee move up in the organization, or unlock a new level of performance they didn’t know they had in them…that’s a pretty cool professional win for me each time. ---------------------------------------------------------------------------- Everything written above is some variation of the answers I’ve given searchers over the years. I’m trying to answer the implicit questions the prospective searchers are asking, which is actually just “Should I do what you did?” That’s the real question being asked, so I’m willing to spend the time and spill the ink to try to help them answer it. But my honest answer for myself? When I’m not holding the weight of having an impact on someone else’s life choices? Absolutely it was worth it. ---------------------------------------------------------------------------- I’m finally doing something worth doing. I get to build an organization with staying power. I get to build something that impacts people in a direct, tangible way. I get to do something that comes with umpteen moments of failure, but without a truly catastrophic one (yet). The near-constant brushes with failure drive a form of personal learning & growth that is orders of magnitude greater than just about any other path I can imagine myself on. In many ways, the significant exposure to failure is a sign that this is worth doing. To be clear, that’s not a 1:1 relationship — there are lots of very risky things that are not worth doing (heroin comes to mind). But in this case, the exposure to failure is a feature, not a bug. Learning is found through failure, not through success. We know this inherently, but have been so trained to avoid failure. ---------------------------------------------------------------------------- I could write about failure for a long time. I’m currently reading How To Try Again, by Steve Kamb, and the first chapter is basically an ode to failure. This passage stood out to me: ------------------------------------------------- “We stand on the shoulders of past us. We not only have to thank our past failures for getting us here, but we can be proud of them. They make us who we are, and taught us everything we know. Maybe it took us longer to learn some lessons than others, but I think that’s okay too. We get to bring all that knowledge with us. That means there’s hope for us yet! Failure isn’t the end, but the beginning.” ------------------------------------------------- It got me fired up to write this blog post. It’s a freeing philosophy, isn’t it? If failure is just the beginning, why are we all trying to avoid failing? We should be hurtling headlong into (calculated) risk, and selecting for adventures where failure is an option. Failing doesn’t make us failures, it teaches us how to grow. As Kamb notes in the book, we are fighting evolution here. In the caveman days, failure could lead to death. Today, the stakes are not that high, but our bodies don’t know that. We’re also fighting decades of training. If you were raised to believe any grade below an A was a failure, of course you want to stick to a tried & true career path today. The ranks of finance & consulting & corporate America are replete with high achievers who chased good grades their whole lives and now receive half-step title increases everyredactedmonths. (Not a dig, I was one of them.) If you’ve gotten that sweet, sweet “promotion” from Analyst to Associate, you know what I mean. (Or worse, they don’t even bother changing your title, they put a new number behind it…PM 1 to PM 2 to PM 3.) Short of unexpected layoffs (which is a real, yet understated risk inherent to W-2), these jobs are designed to insulate you from failure and discourage personal risk-taking. To close, let’s bring it back to search, where a massive segment of prospective searchers fit this mold — crushed in the school and their careers to date. ---------------------------------------------------------------------------- When prospective searchers ask “Was it worth it?” many are asking “Will I fail if I do what you did?” It’s a natural question, it’s a healthy question in fact. You should understand the risk calculus, the pros & cons, the gives and takes. It’s not the right path for many. You have to be honest about it for yourself. But you also have to understand that if you go down the small business path, you WILL fail. You will fail over and over and over. You may even go bankrupt. The learnings from that kind of failure are immense. That growth is worth it to me. It may be worth it to you. The learnings from going personally bankrupt may not be worth it to you. That’s a choice you have to make for yourself & your family. But avoiding failure is not going to happen on this path. But you know what? You know that soft, underlying discontent feeling you have in your current day job? It may be coming from the fact that you’re not exposing yourself to enough failure…it may be time to change that fact. Again, no definitive answers here, your mileage may vary, yada yada yada. But if you haven’t failed in a while, you haven’t grown as much as you could have. Consider that when you ask yourself the question, “Is it worth it?” ---------------------------------------------------------------------------- Conclusion A parting thought — small business ownership is not the only way to expose yourself to failure. The right job, with the right team, doing something worth doing — that has it too. I believe my team at Blooma has exposure to failure, but with more guardrails than being a small business owner. We’re doing something worth doing, with people we like doing it with, and there’s no guarantee of success. That’s a level of failure exposure that is right for most people. So please don’t read this and go chasing risk (recall my caveat earlier about heroin). The key takeaway is simply that you don’t have to allergically jump away from the risk of failure. ---------------------------------------------------------------------------- Ask From You Tell me about your failures and what you’ve learned from them. I’d love to hear about them. I know my small business readers have failed a lot, so join the party with me. If I get any good responses (and you’re okay with it), I’ll share it with readers in an upcoming post. Also, if this resonated with you, please share it more broadly. I’m trying to build out my reader base and get this in front of the right people — small business owners, searchers, prospective searchers, anyone looking to blow up their lives. And if you're not subscribed to my blog (Big Deal Small Business, been writing it for ~5 years now), please check it out so you get these posts directly. I post them occasionally on Searchfunder as well, but the full archive can be found on my Substack page. Check it out here: redacted Thanks, Kaustubh