Much needed perspective

Crissi Cole
3 min readAug 8, 2021


For founders, entrepreneurs, leaders and anyone trying to make it all work.

Life comes at you fast. No one shares the “messy middle” — the moments before or after success. The low, lows. The tough sh!t.

I vowed to do that w/ my new venture. Because our realities are distorted by overwhelmingly positive social media posts & perfect resumes on LinkedIn. That isn’t real life.

I write this as I sit on a heating pad to nurse my bruised bum (IVF) on a Sunday. #goals

This article is not for sympathy — it is to try to paint a new picture of a female CEO. It is to reflect on some stories I had in my head about who I thought I had to be — that I now realize I certainly DO NOT need to be. And how the men in my life stepped-up majorly, showing me that I do not have to be everything to everyone, there is room for co-ed care-taking, and we just have to let it in.

  1. CEO: Always working, Always hustling, Always directing (NOPE)
  2. WOMAN: Primary caregiver all day every day (NOPE)
  3. WOMAN CEO: Tough, Conquering all, Hides vulnerabilities (NOPE)

I haven’t worked in almost 2 weeks, and not because I was on vacation. Last minute, unplanned, unscheduled, chaos. Tragedy right? No.

The short story: dad unexpectedly in the hospital (to FL), embryo transfer finally scheduled (to NY), mandatory “modified bed rest” from doc after IVF transfer (to bed).

The world saw my face on Penny’s Instagram the past couple weeks— big smiles — launching our new website, explaining crypto, and more. Those were planned/recorded BEFORE my personal life came rushing in.

This is me right now. No makeup. No appetite. Cuddled up in bed. Same sweatshirt for 5 days straight.

Me w/ hubby in NYC hotel during frozen embryo transfer

Just because you are a CEO or a founder or leader doesn’t mean you have to put up a front.

Lessons learned:

  1. MEN: My brother and husband stepped-in to care for my dad and me without hesitation. YUP. I could have never survived w/o them. I want to celebrate them. The headlines in the news rarely celebrate men. It is always a variant of “women do 4x the times of work at home” or “women bear the burden at home” — and while I am not saying the world is perfectly equal — I do think we need to share more stories that show how gender doesn’t define your ability to care, just like gender doesn’t decide who gets to invest & grow their wealth! It goes both ways.
  2. BIZ: I have had my head down so so so laser-focused on launching my startup this past year, that I forgot about one of the main reasons I quit my corporate job for entrepreneurship. Freedom. Freedom. Freedom. HELLO. My schedule, my rules, my way. I would want every single one of my employees to close their computers and run as fast as possible to their families or themselves when something happens. Why shouldn’t I do the same without guilt? And, heck, when you see your biz running so damn smoothly when you are gone, how is that for a win? Trust your team and build sustainably.

3. MINDSET: so many thoughts….

control is overrated

its ok to not be ok

its ok to be happy and sad at the same time

its ok to ask for help

its ok to step away from your job, business, work

freedom and flexibility is priceless

life is random

positivity goes a long way

when things are good, let them be good

gratefulness > sadness

therapy is worth every penny :)

PS. My company is Penny Finance, an early stage startup that is taking on the wealth gap. I am 32, live in Boston with my husband, and have been on a 3-year fertility journey because of PCOS.



Crissi Cole

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