Being a new founder, and a new parent

Crissi Cole
5 min readSep 16, 2022


Where do I even start.

My team told me to write a post about maternity. OK.

Just sitting down to write this post took me a couple months…because I was an anxious delirious mess — how could I possibly write an organized article about it?

In April I had a baby. The cutest, most hilarious little baby girl.

[Side note, I did a tech release the day before going into labor…. I didn’t start off the journey off in the most balanced way…]

I had the greatest excuse to NOT be doing all the things. Yet I still felt this overwhelming guilt, this constant disappointment that I am not doing enough for my business, for my family, for myself.

So what was the maternity plan?

I attempted to take a 2 month maternity leave. Clean separation I thought. That will help with the guilt. I spent months getting my team ready, pre-planning it all. My board and team were supportive. Beyond supportive.

Ooo la la I thought. A little mini break from grinding, emails on emails, meetings on meetings. It should be the best 2 months ever, right? Wrong.

First of all, maternity and paternity leave is not a vacation. Sleep deprivation + post partum anxiety + hormone drop + taking care of this new fragile thing = the most overwhelming time in the entire world.

I really did try to do the leave right — and focus on my health and my baby. But it was almost impossible. I was constantly thinking about my company. During the hours rocking Charlie or feeding Charlie or bathing Charlie, thoughts and ideas about Penny would pop into my head. But there was nothing I could do about them — I couldn’t sit down at a computer and write that email. I couldn’t get on a Zoom to meet that person I serendipitously ran into on the streets of Boston that I knew I should absolutely start building a relationship with. Talk about insanity — my mind was about to explode. Thoughts multiplying with nowhere to go. And I was exhausted and emotional. Madness.

So, what did do?

I decided I would dedicate 5 hrs a week to Penny (this was 15 days after giving birth) so I could tackle the critical stuff, keep things moving, and satisfy my brain that wouldn’t shut up.

Terrible idea. Terrible. 5 hrs opens the can of worms. I was not fully present in either my mom life or my CEO life. So, I extended my maternity leave to 3 months, and did everything I possibly could to shut off my brain and change the unrealistic expectations I had.

Evidence of why it doesn’t work….

The mantra’s I had to repeat to myself on the regular:

My business was in a good place.

A pause is OK.

The momentum won’t be lost.

We won’t run out of money.

Did I actually believe them? Not really. It just got me through the days.

Until one day on a stroller walk (as I try to multi task updating a Trello card while pushing her) I notice Charlie discovering the blue sky for the first time. Her eyes lighting up. Big smile. Wanting to lunge out of the stroller to be closer to the sky. And I stopped working.

I slowly learned to love my days with baby girl Charlie, and cherish every second I got with her. When I am taking care of her, I am fully with her. That is not the time to think about slide 4 of my investor pitch deck.

I write this without some major epiphany or some great advice to share. I think honestly it’s just therapeutic to say it all out loud, so I can stop dwelling on the should of could of would ofs. And hope that others who are in the same position as me can see that they are doing just fine. And there is no way we can ever do it all. All at once shouldn’t be the goal. Chunk life out, and eventually you may achieve it all.

I hope you can also see that if you are just thinking thinking thinking of all the things you should be doing, you’ll miss the greatest little moments happening in front of you. There is never enough time. And we beat ourselves up about it. We start the day with ambitions to do alllll these things. By 2pm, we are snoozing the calendar reminders, rewriting our long lists, and feeling disappointed that we didn’t accomplish 27 things.

Trying to get the next subscriber, trying to hire that next person, trying to raise that next dollar. What if we thought about it differently…. How can we try to get to the next moment of joy?

P.S. I can’t write this without thanking my husband, who took 5 months paternity leave to co-parent with me, and my mom would let us live with her so we had built-in daycare. I couldn’t have even tried to work without splitting the duties with hubby and mom…. And I could write another longgg article on how we need to change the stigma around dads taking paternity leave. The number of people that were in literal shock that Jordan was home with Charlie makes my blood boil. A topic for another day.

I am Crissi Cole, the founder of Penny Finance, an early stage fintech startup based in Boston. I like to write about the things no one talks about. Because truth rarely makes it online — probably because of fear it will make people look weak or unsuccessful or whatever.



Crissi Cole

Founder and CEO, Penny Finance. Former VP @ Goldman Sachs.