"I Want to Start My Own Company, But I'm Scared"

How to be brave and finally start your own thing

Welcome to “I Have a Burning Question,” where I answer reader submitted questions about careers, work life, purpose, and what to do next. Below is a question from a reader, Laura (in italics) and my responses interspersed.

Have a question? Submit yours here.

Dear Mandy,

I’m a nurse turned product manager at a seed-stage startup who dreams of owning their own company (and destiny!) one day. For more context, I graduated with my BSN degree in 2018 and, while I was in school, created my own company centered on empowering and resourcing new parents. I won pitch competitions at my university and leveraged the resources available to me as a student to start my LLC and get legal paperwork in order. Ultimately, it was either time for me to formally fundraise full time or start working as a nurse upon graduation. I was so intimidated by the process and something felt "off" to me about going to VC firms. I did participate in a few pitch sessions, but the older men (so, like 95% of the rooms) did not *get* what I was working on.

Laura, this all makes sense. Often, when graduating from a program like nursing school, we want to hurry up and start working already! All that school is theory, and we want to put our skills into practice. We want to pay off our debt and make the degree pay off. I totally understand why you were turned off by the VC firms, they can be a judgy bunch, and companies that connect and inspire can be a little confusing for their left-brain minds. Go on.

I decided to work as a nurse and thought I could work on my dream part time while on my "off nights" (working 7pm-7 am). It probably doesn't surprise anyone but myself to hear that I realized working full time in an emotionally and physically taxing job did not leave much capacity for creative outlets (lol, shock I know!). I thought it was the fact that night shift was exhausting me, so I took a full time day shift job and...same problem. I have since left bedside and worked at 2 seed stage companies to get startup experience and find myself feeling called to do my own thing. The only problem is that I am terrified, and I don't know when the "right" time is while I am developing highly applicable skills in my current role.

You are exactly right, I always warn people about the fact that you will care about your 9-5 job. You can’t help it, because you’re good at your job and want to do well! It’s like when you go to a party and you start loading the dishwasher and helping to bring the seltzers in, I mean, I’m here — I’m not just going to stand around, right? It definitely becomes all consuming and I already feel like you’re ahead of the curve and very self-aware for acknowledging this dynamic.

I want to own my own small business creating resources and content for new parents. The problem is that when I express my goal, people who love me tell me that they are surprised. "You seem better than ever! You are so stimulated in this job! Think of how much you are learning!" And I know that this is all true! I am also getting a lot of visibility for this current role as our company grows in success.

Oh! That’s because you are a happy, boppy person who exudes a positive energy — so everyone is absolutely shocked to hear that you may not be totally satisfied and that you may be looking for something else. This is also, secretly, scarcity mindset. “You have it soooo good! Why rock the boat!?” I don’t mean to be rude, but you just have to ignore these people. Especially the ones who are like, “think of how much you are learning” — that comment IRKS me. Yes, think of how much the peasants in the factories during the Industrial Revolution were learning! No! You don’t get it! I would learn something no matter where I go because I am a learner and I give a shit. I don’t want to just learn, I want to create something from nothing. Again, please ignore these well-meaning friends. Gahhh!

I originally bought your Should I Quit journal because I was suffering from serious bouts of anxiety in my current role. I have no history of anxiety previously and started taking Prozac for the sheer necessity of "making it through." I do feel much better on medication, but I realized through reflection that I am just medicating myself for the situation. My score on the Time to Leave questionnaire is 11/12, which was a helpful way to quantify why I am feeling so confused.

Again, excellent on the self-awareness. 11 out of 12 on the time to leave questionnaire, I believe that correlates to “time to get the F out.” Thank you for also normalizing taking medication to try and heal yourself, and for it being a necessary part of the process, which is a personal decision and supported!

As the first employee at this startup, the company and job have changed significantly since I joined the team 2 years ago. As time goes on, I realized that managing the founder (CEO) is the hardest part of my job. He is a good person, and I like his vision for the company, but the way he is vocally anti-empathy and doesn't want people at the startup to feel psychologically safe is in direct opposition to my own philosophy of work. As we bring on team members, my energy is more proportionally spent being the social shock-absorber of the team and "fixing" his culture. (I am also the only female on the 7 person team and the youngest.) Page 8 of SIQ taught me that I have a pattern for finding and working with demanding individuals or jobs that drain myself--and I take full responsibility for the part I play in 1) seeking them out and 2) not setting high-worth boundaries from day one.

Ohhh he’s a founder, alright. It’s basically just fear. In his mind, this is his baby, his creation, his one chance to become a millionaire. So he’s going full Silicon Valley bonk — taking life by the horns and squeezing every bit of joy and friction and risk out of work — he’s not taking any chances. He’s hard on himself, probably one of these people that has a restricted calorie diet, pushes himself too hard, has a negative inner monologue (or self-aggrandized stuff, or both.) So he pushes that onto the team and creates a culture of anxiety; emphasizes productivity and effectiveness. THIS IS THE COMPLETE OPPOSITE OF YOUR STARTUP IDEA, BY THE WAY. You want to create resources for parents, he wants to eat everyone alive. Please. I’m giggling in horror. You sound like such a nice person! Noooo don’t be the shock absorber for the team!!!! Don’t do it! You’re too nice! When you leave, other people will leave, too. YOU KNOW THAT’S TRUE.

Also, I am absolutely delighted that you abbreviated the Should I Quit journal to “SIQ” hahahaha — it has taken on a life of its own and has a dedicated lexicon I LOVE IT.

Nobody on the team asked me to do the emotional work I am doing, but I also hate the idea of doing less. I find the more I try to have boundaries (like not reacting or jumping in reflexively to improve something) the more I dread the work altogether. I am also not going to change who the CEO is as a person. Maybe the real lesson is that I need to work with emotionally-intelligent individuals, but I can't help but feel that this is my own sensitivity and *highly* unrealistic. Also, as I mentioned above, I really want to own my own company and spend all my time on that, but I have this expectation that, to leave a job like the one I have, I will need compelling evidence that it is better than what I am currently doing. When I go to work on it, though, I am all out of capacity. (Another pattern: I don't leave creative space for myself.)

GIRL you have what it takes to start your own business, which is that you have an appetite for emotional work. Right now, it’s just being misdirected in that it’s being used to realize someone else’s vision. But a year from now, when you’re running your own business — that ability to handle the emotional roller coaster — is going to pay dividends.

You really can’t change the CEO as a person, and I guarantee you that will be the culture for the entirety of his reign, probably even after he leaves/is kicked out (lol, just sayin’). Your sensitivity is your super power. You have empathy. Yo know what the good people need. Again, you’re just using it in the wrong place, wrong time.

GET OUT OF THERE!

A note on compelling evidence: you have to create it.

Part of being a founder is believing in something before anyone else. You must have this unwavering belief (aka “being delulu”) three, sometimes six months, before the rest of the world catches on. Did you know that I had to pay $85 for a binding machine to make my first Should I Quit journal, before it even existed? I had to have an irrational belief that it was going to work, and even if it didn’t who cares, because at least I tried. Did you know that before this journal, there were two other self-published books that never sold a single copy? And before that, I used to have a Should I Quit quiz on my website as a lead magnet, that only had two downloads a month?

Failure, failure, a hundred small and spectacular failures before success.

What I’m saying is: you have to be the first one to believe in the thing, and take the leap, AND, your first few tries will probably not work, will probably be a big flop. But it’s the chase that’s important. It’s the search, the constant yearning, that is part of the fun.

And only sick people like entrepreneurs will find it fun. Join us! It’s great here. Oh, also, after you leave, please take at least a month to detox and read some good fantasy novels and watch Netflix and eat fried chicken (or fried jalapeno poppers if you’re veg) before you try and conquer the world. You’ve worked soooo hard and you deserve a little break.

What Are Your Options?

My options are as follows:
1. Stick it out in the role I have while trying harder to work on my own ideas on the side.

No, absolutely not. That’s what you’re doing now. It’s not working.

2. Stick it out in the role I have and just save my ideas for the fantastical state of "Later" while my equity vests in hopes of a great acquisition.

No, because you’ve probably already vested enough equity (at least 1/3 or 1/2, right?), and it’s probably not worth it. Unless there is an acquisition currently in progress, don’t hold your breath. These promise seeds are what they sell you. Do we really think your smallest-man-who-ever-lived CEO could actually swing an acquisition event? I feel like he’d do something stupid to mess it up, no?

3. Quit the role I have now without a job, and see what I can do working by myself and for myself.

Yes, scariest option. I am leaning towards this one, obviously. Year one of entrepreneurship is super hard and full of mistakes and trying to figure things out. Year two you get some momentum and start seeing results. Year three is awesome and you see all kinds of possibilities and you start making more money and finding your groove. It’s a climb. It’s a terror. So you might as well get started on it now.

The sooner you start eating this shit sandwich, then the sooner you can reap the rewards. Also, forget the rewards. The real reward is becoming the kind of person who takes a chance on themselves, in spite of it being very risky, and has the tenacity to see it through.

Idea: is there a way you can start making money, with individual clients — either coaching or consulting or designing or selling a physical product — to help bridge the financial gap? I feel like you have some great, marketable skills. That way you don’t have to get too attached to a company, and can still do things on your own time.
4. Like option 3 but get a part-time job that takes less mental energy and effort (and probably has less pedigree) with the goal of my compromising time-spend on my own ideas.
Yes, but you have to be very careful what that is — because you’re a good, smart person so even a part-time job has the ability to eat all your time and energy. “You’re so good and talented, thank you so much, could we bump you up to 10 more hours a week?” Run!!! PLUS, even if you do this, all roads lead back to #3 eventually.

5. Look for a similar job to the one I have full-time to continue gaining the skillset I am at this company (but still not solving my own entrepreneurial itch).

No. Please. Same shit, different day.
*I am also married to a partner who is very supportive of me. He would agree to any of the numbers above, even if it meant we had to live on a tighter budget.

I love this so much for you!! Ah, to find one’s soul bear who is supportive when it counts. This makes me feel better about #3. How about you two save up a nice little nest egg, maybe enough to cover four or five months of runway. Then, cut down your expenses and go into lean mode. Cook at home more, track your expenses. Then, save even a little more, just to calm your reptilian brain (which will be screaming at you). At that point, take the leap! Just do it. You can always go back to startup world if it doesn’t work out (though, in all probability, you’ll be so good you won’t go back).

Sending you support and good vibes! Thank you everyone for reading.

xo

Mandy