Startup Mom
A blog based on my experiences building ParentScheduler and Frever

Regroup - Rethink - Restart

About starting fresh on something you’ve been working on for a while.

01 Feb 2021, 4 minutes read

In my last post I mentioned how, following the interview at YCombinator, I felt the need to stop and take a week of not doing. After that week has passed I felt incredibly demotivated. I struggled to keep going. I considered closing down. Not because I didn’t believe in the problem I am trying to solve or even in the direction I am going in. I just couldn’t find motivation to work. I was tired of pushing that big rock up the hill.


When I considered closing the business I started wondering what I would do instead. But nothing else excited me either. This was very uncommon for me. I am usually a pretty decisive person. It is often easy for me to make a choice, be it “what should I eat?” or “what should be my next career move?”. And suddenly I felt vacant. Vacant of will, vacant of motivation, empty of knowledge on how to direct myself from here. As I said, very uncommon for me.

Being influenced by the Dao as I described before, I tried not to freak out, and not to jump into a decision just so I feel on safe grounds again. Could I stay in not-knowing? Phew, that’s hard. For me at least. I hate not knowing. I struggle with inaction.

In the days that followed I slowly realized something. It is not that I lost my faith in the problem or my belief that there is a need for a solution, like I said. It isn’t even that I lost faith in the direction my app is taking. No. It was faith in myself, in my OWN ability to make it work, that I lost. I realized that the application process and interview with YCombinator has disillusioned me. Not because of the rejection, I knew chances are small. But something in the process made me realize how small I really am. Just a tiny little Tamar, in this huge world. Rationally we all know we are small, but practically (and naturally) we are the heroes of our own play. The center of our own existence. Something in that process confronted me with my own insignificance and while it is all true - I am a very small human being in this huge wide world and I know that my existence, while significant to myself and my close ones, is not that important in the grand scheme of things - the problem was that I let this true reality not only be true, but break my spirit.

In some psychology processes as well as in meditation we try to introduce a gap - a gap between our external experiences and our internal reactions. But in this case I struggled to create that gap and I was lost in my emotional reaction.

So what changed? Why did I decide to proceed and how?

I was on a long drive, for me it is one of the best places to think, and my thoughts flowed as such:

  • “I feel so disillusioned - building a startup is incredibly hard and requires a lot of knowledge and skill. Being able to build a product isn’t enough.”
  • “More specifically - I was hand waving my business plan and marketing plan.”
  • “Wow, I was so naive”
  • “If I was to start all over, with the knowledge I have now, what would I do differently?”
  • “Would I tackle a different problem altogether? Would I take a B2B (business to business) approach like going through schools, instead of a B2C (business to consumer)? Would I have stayed as an employee and not opened a startup at all?”
  • “No. If I were to start all over I would probably do the same as I believe in the problem space and I believe in my approach to solution. I would, however, build a much better business plan and a much better marketing plan”
  • “Well Tamar,” I told myself, “there is literally nothing stopping you from doing that now.”

Wow. Talk about blowing your own mind. I guess it’s true, I could “start over” with the product I have, but rethink my business plan and invest more in marketing.

On that drive and in the following days I decided to:

  1. Change my business plan to require a subscription up front. This isn’t only about being paid (though that would be nice ;), it’s a step up in how I value my work. While getting feedback is crucial, I have neglected one of the key ideas of lean startup - validating people will not only use, but are also willing to pay, for your value proposition (depending on your model of course).
  2. Invest in marketing. I have exhausted my personal Facebook, LinkedIn and other circles. Honestly close to 400 downloads from that alone is more than I could have hoped for. Now it’s time to get a fresh and exciting marketing effort going.

It was tough, doubting myself that way. But it helped me regroup, rethink and restart my business. On to the next phase in this voyage. I wonder what the next turn will produce.

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