The Unaddressed Mid-Founder Life Crisis

An Actionable Case Study.

Nina Church
Sep 5, 2018 · 9 min read

This is part of a series of anonymous case studies of problems young, scaling startup founders face. This (and all) case studies are shared at the request of the person involved, out of a desire to share their experiences.

If you have a case study to share or a problem you’d like to see addressed, please email nina@prismaticco.org. About the interviewer: Nina Church is an executive coach who specializes in coaching startup founders under 30 into their full leadership potential.

The Challenge

Founders, especially young founders, often hit a point of questioning how the heck they got where they are, and whether they should leave their company.

This can be caused by a variety of stimulus: stress in the cofounder relationship, fear over how long a startup ‘locks them in’ for, realization that they’re not interested in the company domain/solution, desire/passion for new areas, learning more about what they value in their personal life, general stress… The list goes on. The point is, just like a mid-life crisis, this is a widely common and unfortunately unspoken problem for many people that can lead to depression, guilt, and company destruction if not properly addressed.

The Case Study

All names changed to protect anonymity.

Jane was 2 years, 9 team full-time team members, and $3 million of venture capital into her startup when her mid-founder crisis came on. It started slowly — it was just a little harder to get out of bed in the morning, a little less fun to do that weekend work. She didn’t think much of it. Things her cofounder or direct reports did seemed to annoy her a little more than usual, and she found herself venting to her partner more and more frequently about their inaptitude. She started reading and researching about how to be a better manager and leader, and the more she read the more she felt the company was behind. And feeling behind soon turned to feeling doomed, unless she and her cofounder stepped it up — way up. She looked at the changes that would need to be made and the reality set in on how hard it would be to turn this company into a multi million dollar company.

Years earlier, she had jumped at the opportunity to start the company because of her ‘insider secrets’ that led to the product and because she was in awe of her cofounder. She naively had thought it would be a few years until they could flip it, learning a lot and making a lot in the process. Now, she viewed the secrets as all but worthless since they clearly hadn’t found product/market fit and she was her rose-colored glasses around her cofounder were off. She didn’t find the product or problem area that interesting, but there was so much learning early on that she hadn’t really noticed. Now, making this company win was going to take a lot of stress and time. 10 years. 15 years. 20 years. More personal investment. More stress. Putting her personal life on hold. Committing herself to her cofounder and the current culture for all that time. Could she do it?

She felt paralyzed. Could she leave the company now? She had recruited these team members — they had families, bills to pay. She had recruited their investors — they had put their money and time into her. She had made commitments to her cofounder — he had put his trust into her. Going felt impossible. But staying? Could she really commit to this lifestyle, this problem area, and the low-odds for the next who knows how many years? She tried to focus on the positives, but it never lasted long. The constant argument in her head drained her day and night, until she found herself in a depressed state for the first time in her life. She wasn’t showing up well at work and she wasn’t showing up out of it. Normally an incredibly happy person, a brief suicidal thought even crossed her mind at one point. That’s when she knew it had finally gone too far and committed to formally solving it.

The Coaching Solutions

Over the next 6 months, Jane tried a variety of systems:

  1. Getting advice from friends and family. This was challenging because few people truly had empathy for her position and could give her meaningful advice or unbiased strategy support.
  2. Writing / processing her thoughts on paper. Anytime she couldn’t sleep she’d write out her thoughts. But just like in her brain, she had no way to process all the thoughts and make a decision she felt good about when so much was at stake.
  3. Trying to commit & stay present. She tried to push out the thoughts, but that rarely worked. She mediated, did yoga, and tried to get peace of mind but the more she pushed the conversation away the more it seemed to come roaring back.
  4. Talking to investors. This was challenging because of the heavy bias and feeling like she couldn’t be honest with them. She approached it with high sensitivity and didn’t feel like she was able to be direct enough with them for it to be useful.
  5. Talking to her cofounder. This was challenging because of the heavy bias and feeling so bad about letting him down.

With runway getting shorter and pressure getting higher, Jane reached out for a coach. Here’s how it supported her transformation:

  1. Created a personalized decision making framework to process every option. Combining her life principles and long-term goals with decision making strategy and meaningful career data, we built a personalized framework for processing such a big decision that she could feel great about. Ultimately, the process led her to decide that she wanted to stay and turn this company into the one she always dreamed of running.
  2. Shifted mindset & emotions using motivational interviewing, CBT & other psychology tools. Used for a wide variety of psychology applications, motivational interviewing and mindset work helped change Jane’s emotional state from being back and forth on the decision to being fully committed. It also helped us uncover what she needed to turn this into a total win: in her case, she wanted to get as much professional development out of this startup experience as possible, which could serve her later in her career.
  3. Developed a professional growth roadmap & execution plan. To feel good about staying, Jane wanted to maximize the growth at this startup. We executed a mini-360 review to get a full picture of her strengths to invest in and fatal weaknesses to combat. We prioritized the list and now spend 45 min of each 1.5 hour session every other week working on one area.
  4. Facilitated key conversations with her and her cofounder. She had a lot of changes she needed to make to feel good about staying, both in how she showed up and how she demanded her cofounder show up. These conversations can be really challenging alone, and bringing in a coach can keep things positive, productive, and actionable. On our call we set clear expectations for themselves and their team members, cleared previously unspoken feedback that was weighing them down emotionally, and defined new company-wide goals/metrics.
  5. Scaling the company quickly and effectively with limit coaching. We never wanted Jane to be in the same position again. So we designated 45 minutes of our bi-weekly (2x/month) sessions to defining & troubleshooting her biggest success limit: we look at the company’s long term goals (in her case quarterly goals) and ask, “what’s the biggest limit to getting this?” We then discuss possible solutions, and create or check off right then actionable items to getting there. Some sessions, Jane needs help recommitting to her decision or processing a personal problem that’s distracting her, and that’s fair game too.
  6. Ongoing emotional support via text. Jane can text her coach anytime for quick questions, pep talks, or for a quick emergency coaching session. Early on, Jane used this a lot the minute she started to fall back into an unproductive ‘thought loop’ about leaving or staying, or when she noticed she was shying away from doing the hard work or giving the tough feedback.

Next Steps

Jane’s decision was just one of the many options that she could have chosen, and each situation and person is unique. If you’re struggling with a similar scenario or see a mid-founder crisis in your future, know that there’s no one wrong answer. There is, however, a best option for your values and goals. Seeking the right support system to figure out what that option is is critical.

You might decide that working with a coach isn’t the right option, and from a business perspective that’s fine. But from a personal perspective, it hurts my soul because I know how much struggle can be avoided and upside can be gained. You don’t have to address these big questions alone, and you can feel great about your decision — whichever way it goes. On top of that, every person really needs to answer very different questions in order to figure out the right solution, and needs personalized post-decision support. If you’re ready to break the stressful-edging-on-neurotic thought loops, make and support your mid-founder crisis decision(s), reach out now.

That said, if you decide not to work with a coach, I recommend asking yourself the following questions:

Am I using sound evidence & critical thinking to make this important decision?

  1. Have I talked to at least 3 people who were in similar positions to me, and chose to stay? (yes/no)
  2. Have I talked to at least 3 people who were in similar positions to me, and chose to leave? (yes/no)
  3. Am I taking 100% responsibility for making this decision? (yes/no)

If you answered no to any of the above, pull out your calendar and contacts and make it happen before going any further.

  1. Do I have proprietary ‘secrets’ that I can use to start a better company or recruit a founding team? (yes/no)
  2. Am I one of the top people in my field, and therefore likely to be recruited for the position I want by a top founder? (yes/no)

If you answered no to both the above: Would I be prefer to join an amazing team with less control / not as a cofounder until I have/am one of the above? (yes/no) If your answer is no to that AND you answered no to both the above questions, the reality is it’s unlikely you’ll end up working with a better team on a better company at this time. That’s not definitive, but think about it from the perspective of a founder who does have the amazing vision and the critical thinking capacity: this person could work with anyone in the world. Would they work with you at this moment? If not, how could you use this experience to become the person that they’ll want to work with by your next venture/opportunity?

Do I have the variables of satisfying work?

“According to self determination theory, intrinsic motivation, which we often connect with passion and being satisfied at work, comes from three things:

Autonomy — some sense of control over your time

Competence — the feeling that you’re good at your work

Relatedness — connecting with other people in the process

So Good They Can’t Ignore You, Cal Newport

  1. Would I have more autonomy over my work if I leave? (yes/no)
  2. Does this job present opportunities to distinguish myself by developing relevant skills that are rare and valuable? (yes/no)
  3. Do I connect with the people I’m currently working with? (yes/no)
  4. Do I have to work with anyone I extremely dislike and can’t find a way to repair the relationship with despite total effort? (yes/no)
  5. Does this job focus on something I think is useless or perhaps even actively bad for the world? (yes/no)

If you answered ‘no’ to any of the above 5 questions:

  1. Would that specific answer certainly be different if I were working somewhere else/on something else? (yes/no)

If the answer to the above is yes, then job research would say you should consider finding a different job.

If the answer to (A) is no (or the answers to questions 1–5 are yes), you currently have all the elements that research says makes for satisfying work. It’s just a matter of pushing through.

What do my principles say?

  1. Do http://selfauthoring.com/.
  2. Based on your self authoring answers, create a ‘weighted scale’ of your life values/principles and goals. (Excel works. Put the value, then put next to it a ranking of 1 to 5 for how critically important that value is to your overall life satisfaction. I.e. you might put ‘ability to show up for my friends/family in times of need’ with a weight of 5 meaning you never want to compromise on that value.)
  3. Run each option through its ability to be done in line with your values and to support your goals.
  4. Look objectively at the results. How do you feel about what objectively comes out as the best option? If you don’t feel emotionally onboard but this and your other answers point to a specific decision, answer: “what are the 3 best reasons to go with this option?”
  5. Ask “what do I need to feel good about my choice?” Take any necessary actions to make this happen.
Nina Church

Written by

Let's light up the world from the inside out. https://www.prismaticco.org/

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