From Boiled Frog to Burning Platform: When Is It Time To Quit?

Everyone I meet eventually wants to quit their job.

I have been joking lately with colleagues that whenever I meet a new person networking, by the end of the conversation, they tell me they want to quit their job. I am exaggerating, of course. But there is a certain consistency to the phenomena that when people reach out to a coach, it’s usually because they want to change. And something about the way I talk to them like they are a real person, and ask them questions that show I genuinely care what they think and how they feel, seems to push them over the edge.

The pandemic has only accelerated the phenomena. In some cases, layoffs are forcing people to find new ways of generating an income. In other cases, the severity of the situation has caused increasing numbers of people to completely rethink whether their job is really providing them with the fulfillment and meaning they desire. Faced with either scenario, some seek employment in a new company, while others decide it is finally time to start a new business. I’ll be dealing with the latter in this piece, and the former in articles to come.

New business founders tend to fall along three different distinct scales. Discovering where you fit on each of these three scales can help you identify where you need the most help. First, there is the younger and more impulsive founder versus the older and wiser but overly cautious one. Second, there is the founder with deep domain knowledge versus the founder with the idea but no background in the space. Finally, there is the founder obsessed with their one big idea, versus those who cycle through ideas like tissues.

Impulsive or Perfectionist

This scale is on the surface a generational divide. But if you look closer, it is more about mindset than anything else. The young and impulsive founder is the basic stereotype of a Silicon Valley tech dude. Usually men, but not always, they are a few years out of college. They are smart, confident, and eager. They haven’t had the benefit of living through a major economic meltdown (until now, perhaps), so they don’t really think about risk the same way that people who have lost a lot of money often do after the experience. They don’t know that they can fail, or perhaps they don’t put much weight on failure, so they are emboldened to take extraordinary risks, and this helps them endure the extreme uncertainty of starting a business more than most other folks.

On the other hand, they are pretty clueless. Lacking significant life experience, they don’t know what they don’t know, and often aren’t particularly curious about it. They have a vision for the future that is as bold as it is unrealistic. They have a hard time listening, and gaining knowledge through feedback, because no one has ever told them “no” before. When faced with an obstacle, they simply shrug it off and keep trying.

The older and wiser founders, on the other hand, tend to be overly analytical. Chances are, they have worked very hard to get where they are, and they are not prepared to take any unnecessary risks until they are reasonably sure that it’s a safe bet. They are patient and disciplined, which makes for good operators, but not necessarily good entrepreneurs. They are prone to sit in their office and design and redesign their idea until it’s absolutely perfect, even at the risk of missing the opportune moment entirely.

The young and impetuous founders are far more likely to jump from a cramped corporate office into a new business venture, but they are less likely to be disciplined enough to thoroughly test their idea with real customers and pivot when they need to. The older founders might sit in their corporate office for too long without ever having the courage to jump.

Domain Knowledge

Some founders have immense domain knowledge in their field, perhaps after working for a large player in the space for a decade or more, and finally decided to go out on their own into the same industry as their former employer. As such, they tend to be overly focused on “beating” their former employer in the marketplace by developing a better mousetrap. They have the advantage of knowing intimately how their competitor thinks after having worked for them for so many years. Unfortunately, this over-focus on the competition can lead them to make a less polished “me too” version of the product that is undifferentiated except for the one or two features that really bugged them when they worked at their competitor. I see this frequently in real estate and finance startups.

The opposite side of the spectrum is the founder who has an idea with no real practical knowledge of the industry. A great example might be a scheduling app for the dentist. They go to the dentist and, while patiently waiting for their root canal, observe some egregious inefficiency in the office process. “By George,” they think to themselves! “How can they still be using email attachments for that process?!” And off they go to design a perfect solution to the apparent problem. No thought is given to the fact that they are not a dentist, nor have they ever worked in a dentist office. No, no. The big idea is too bright and shiny for their attention to be cast elsewhere.

Big Idea

Lastly, there are founders who again fit the Silicon Valley stereotype of having one big idea that will change the world, they think. What propels them is an indomitable passion for solving one big problem or helping a particular market segment. They think deeply about the problem night and day. They tend to be highly compassionate and empathetic people. However, they are woefully unprepared for the possibility that their great idea simply doesn’t work, and they might have to trash it for a new one.

On the other end of the spectrum is the founder who just wants to be a founder no matter what. They aren’t really sure of the idea, but they know they can't work for anyone else and they just want to “build something big.” They’ll simply have to look for opportunities and try them out until they find something that sticks. Their main problem is that it is unlikely that they will find a market and a customer to truly fall in love with, where they would be driven by the pure passion to help described in their opposite on this scale.

Every founder will fall somewhere on all three of these scales. The point here is that it’s not good to be on the extreme end of any of them. If you can be balanced about your youthful enthusiasm and your methodical design and planning, you’re better off than being at either end of that spectrum. If you have deep domain knowledge, you’ll likely need a partner who has a wider perspective. While if you have no domain knowledge, you’ll want to partner with someone who does. And if you’re really into your big idea, I’d suggest mostly falling in love with the people you want to serve and getting comfortable with solving whatever problems they have even if it doesn’t align with your original passionate idea.

Getting Ready to Jump

So, you’re reading this from your home office between Zoom calls with the coworkers, and increasingly thinking about making the next Zoom call with your boss be the last. What’s it going to take for you to take the leap into the unknown?

There are three things you need to think about before starting your own business: 

1. How much runway do you need? Risk tolerance varies widely among people, but most would be well served to have 6 months to a year’s worth of savings in the bank before going it alone. It’s going to take you at least 3 months to get your first dollar, and then you have to scale from there until you can pay your bills, not to mention having enough revenue to hire staff.
2. Research your target market, but don’t forget to stop after a while. You can’t make your business idea failure-proof by staying home and designing it hard enough. Eventually, you need to get out there and sell something to people, and you really can’t do that while working full time. Your job and your new business are, at the end of the day, mutually exclusive options.
3. Gather your allies. You may need a partner, or at least some mentors and coaches. Starting a new business is insanely hard. No one can do it alone. Make a list of friends, colleagues, and supporters to bounce ideas off of, and talk to when you’re freaking out about it not working (so, at least once a month).

Answer the Call

So, are you ready to be the hero in your own movie, or are you comfortable being a supporting character in your boss’ reality TV show?

Headed to hero status? The 12-Week MVP coaching program for founders is for you. You can review the full details of the program here.

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