Startup Happiness

As an executive coach, I end up talking to a lot of startup founders; I’ve also been one myself, with two successful exits. I’ve noticed that there is a relatively common phase in being part of a founding team that is rarely talked about, so it goes almost unnoticed. It’s the phase where a founder becomes dissatisfied with their role in the company, and has to decide what comes next.

The founder’s lack of enthusiasm doesn’t generally make news: they mask their dissatisfaction until they decide what to do. The process of realizing that something needs to shift, figuring out what it is, and actually taking steps to make a change all happen behind the scenes, and with as little fanfare as possible. The end result can be small but powerful course corrections that are completely internal to the company, or an announcement of a new role or a departure.

That process is more fascinating, and more fraught with challenges than most people imagine. As an executive coach, I have the honor of helping startup founders see the landscape clearly, lay out possible options, test out ideas and possibilities to gather more data, think through options to make the best decision, and then to follow through in the best way for themselves and their companies.

Company founders start with a huge amount of enthusiasm, and the challenge of building a business from the ground up.  Those challenges are a good fit for most entrepreneurs – the work is fast paced, there are lots of interesting challenges, and they are constantly being stretched and tested in new ways. Although the process can be exhausting, most people in this phase are working at their edge, and energized by all the activity and change. During this phase, if an entrepreneur gets stuck, it’s not due to boredom.

If a founder is profoundly lucky and skillful, their company may reach a point, after several years, where they have become a known success. They are one of the top companies in their market segment, and instead of changing continuously, the organization is focused on consistency and predictability, moving into new market segments, improving processes, reducing costs, and maintaining and improving existing products.

It’s during this phase that some founders get stuck. The paradox is this: they have achieved the level of success that most people only hope for, so the majority of people around them are saying “Wow, congratulations… You did it! That’s so awesome! You must be thrilled!” They may also be a minor celebrity in relation to their own company – as the founder, they are the keeper of the company’s early lore and stories, magazines want to interview them, they are recognized and sought after at social events, and depending on the size of the company, even employees often get a big thrill by spending time with members of the mythical founding team.

But in the quiet moments of their lives, they’re asking themselves: “How come this isn’t fun anymore? If I built this company, why don’t I love my job? What am I supposed to do now?”

When they realize they are at this point, most founders are profoundly sad. They started on a journey many years ago to do something that seemed barely possible, built a team that they worked shoulder to shoulder with, demonstrated extreme passion for achieving each milestone, and told anyone who would listen “I’m a founder at company XYZ” with enthusiasm and pride.  It’s a core part of their identity, and they can’t imagine not being a part of the team and business that they helped to create.

Initially it’s hard for many founders to even talk about this conflict – it seems almost disloyal to not love their work, and by association, the company that they built from the ground up.  The information that a founder is dissatisfied isn’t generally in anyone’s best interest to broadcast, so founders can have a difficult time deciding who is safe to talk to. The interpersonal dynamics between founders, boards, executive teams, and investors can be fraught with challenges and competing priorities.

Because it’s hard to talk about, and hard to find someone to talk to, many founders stay quiet and stuck in this situation for far longer than they need to.

Often, my work is helping founders understand what their options are, and how to get to a place where they are happy and energized again.  Sometimes it’s just a single founder who needs to make a shift, and sometimes it’s the whole organization or culture. But if you’re the founder who is unhappy in your current role, it’s well worth figuring out what needs to change, and taking steps to make it happen. Your happiness depends on it!