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Six Lessons I Learned Going from Career Switcher to Startup FounderFeatured

Seven years ago, I felt stuck in a job I knew wasn’t the right fit for me personally. I felt stuck on a career path that had a clear ceiling professionally. And I felt stuck feeling unsure about what the right path forward looked like for me.

I weighed my options. I wasn’t sure which specific profession fit, but I at least understood my priorities and goals. I wanted steady, clear, and tangible career growth with better opportunities at each step. I wanted more flexibility in the way I worked. I was looking for a bigger challenge.

I started researching software engineering and it seemed to check all my most important boxes. I found a program near me where I could get a Masters in Computer Science without requiring a pre-existing background or experience in the field. I applied, got in, and enrolled over the course of a few months.

It was decided: I was going to be a software engineer.

Out of my program, I went to work at a large bank, then eventually joined multiple startups and began learning the ropes of the industry and building my skills and experience. I came to understand how software companies work, but at each stop, I felt like there was still something missing in my career.

As a career switcher, I never thought building a software startup of my own was on the table. For years, I had read stories of startup founders and listened to podcasts and watched shows detailing the startup journey. I admired them, but I felt behind, like I was trying to catch up. I couldn’t imagine myself in their shoes.

Then, a year ago, that’s exactly where I found myself.

Now, I’m building Critter, a mobile app for pet owners. In the time leading up to my decision to go out on my own and in the year since I committed to working on it, I’ve definitely had doubts about whether I was cut out to build a company. I frequently second-guessed myself and worried about failing.

Despite those doubts, I went for it, and I know you can too if it’s what you envision for your career. Here are six key lessons I’ve learned over the last year that might help you on your path.

Lesson #1: There’s no perfect time to start a company.

I am currently seven and a half months pregnant. It’s been a long and sometimes difficult journey filled with ups and downs and aches and pains, but at some point, I realized that there was always going to be something that made ‘now’ an inopportune time to get started. There was always going to be a reason to put it off, because the perfect time doesn’t exist, particularly if you’re typically a procrastinator or if you tend to be a perfectionist like me. It’s a big effort and things will stand in the way, but if you do want it for yourself, there’s a way to make it happen. Plan ahead, be thoughtful about your approach, set boundaries, and dive in.

Lesson #2: Founders aren’t superheroes.

Startup founders are normal people, just like you and me. They have normal hobbies and talents. They read the same books, watch the same shows, and listen to the same podcasts. It’s easy to get caught up in the stories we hear about founders and build them into something bigger than they are, but the reality is that they’re just people who had an idea and got started working on it. It’s true that founders might not always look like you and that can be a hard mental hurdle to overcome, but I firmly believe that there’s not one personality or founder archetype you need to fit into to achieve success.

Lesson #3: Find a cofounder you trust.

Starting a company can be a lot of fun, but it can also feel lonely. It’s important to have someone you trust by your side that you can bounce ideas off of, openly talk through challenges and those doubts you’ll feel, and lean on for support as you build the company.

Lesson #4: Commit to a working style and approach that works for you.

When you have your own company, you get to decide how you work and map out your own daily schedule each morning. It’s important to figure out how to keep yourself accountable because nobody is checking in on your progress. At the same time, you don’t need to hold yourself to a schedule that doesn’t work for you. You can work in spurts and schedule breaks for yourself if that is what works best for your productivity. Figure out where you work best, what hours you’re most productive, and how you organize yourself for success, then commit to doing that every day.

Lesson #5: Learning is productive.

It’s nearly impossible to know everything you’ll need to know to build a company. Whether it’s a new frontend framework, a backend concept, cloud infrastructure, or even the product and business decisions you’ll need to make, there’s always something lurking that you’ll have to tackle for the first time. Give yourself space to learn and know that time spent developing the skill or learning something new is just as valuable and productive as the time you spend building the actual product.

Lesson #6: You’ll have doubt. That’s okay.

On more days than not over the last year, I’ve found myself wondering whether I was really cut out to be a startup founder. I’ve second-guessed my skills and wondered who I thought I was to be starting a company. That doubt can make you freeze and lead to inaction because you want whatever you’re working on to feel perfect. But every day I learn new skills and gain new experiences; piece by piece I am building a functional app. Doubt is normal and I think healthy for keeping you grounded and on the right path, but doesn’t have to determine every action you take.

The entrepreneurial journey can be an intimidating one because leaving the safe confines of an established company with structure, mentorship, and a steady salary is fundamentally scary. But for some people, that journey is worth it, because you get to experience true ownership over your career and personal trajectory, and at least for me, that has felt really meaningful. It’s too early to know if my first company will succeed, and that’s scary at times, but I also know I’ve gained a new sense of confidence, new skills, and countless lessons I’ll carry with me in my career moving forward.

Starting a company isn’t for everyone and if you fall into that group, amazing! Every one of us should pursue the path that best suits us. But if you do think building a startup might be that best path for you, don’t hold yourself back. Jump in and get started mapping out a plan, because you probably have the basic skills to get started and will be surprised how easy it is to pick up the other skills you need along the way.

AdaezeI's profile thumbnail
Congratulations @jahnamcnamara!!!!! I appreciate you sharing your journey. I too am a perfectionist and in turn a procrastinator, planning and waiting for that perfect time. I am learning to be comfortable with 'done is better than perfect', and work out the kink as I go. I wish you the best and I am here to support you in your journey!
jahnamcnamara's profile thumbnail
Thanks so much @AdaezeI!! I appreciate the comment! It's always a struggle being a perfectionist/procrastinator so glad to hear from someone else who is, too. I feel the exact same - 'done is better than perfect' is something I need to continuously remind myself - such an important lesson that really applies everywhere. Wishing you the best, as well!!
johannakr's profile thumbnail
Congrats on your company and thank you for sharing this! I think career switchers are so perfectly suited to be founders. When you've got different contexts as your background, it makes it easier to understand the different nuts and bolts in a business. Much success to you!
jahnamcnamara's profile thumbnail
Thank you so much, @johannakr for your words! Such a good point, it's so helpful to be well rounded and having a wide variety of experiences really contributes to that. Sometimes as a career switcher you can feel behind, but it's 100% true that all of the varied contexts are actually in fact a huge asset. Much success to you, as well!
torizhao's profile thumbnail
This is exactly what I wanted to read! I'm in a similar situation, been working in tech for 6+ years, 1+year in frontend development and wanting to start my own company.Question: Do you think getting a master of CS is needed to go on startup founder route? I taught myself frontend coding but not sure if I should go for a master. My end goal is definitely founding my own company instead of climbing career ladders.Thanks so much in advance!
jahnamcnamara's profile thumbnail
Hey @torizhao! Thanks for reading my post and I appreciate the question! My first thought is that everyone's journey is different, so I wouldn't say a Masters degree is "required" in a traditional sense, as it ultimately depends what type of learner you are. I was coming from a totally different background and had no training in development before starting my Masters. For me, the structure and curriculum of a more traditional academic program was appealing because of my personal learning style, so I decided to go for it. My situation was slightly different, since I pursued the degree as a way to enter the industry in general, but you're already working in an engineering role. Ultimately, I think no matter the level of traditional education you have, there's a ton of things you have to learn when you're a lone developer in a startup, so if you feel like you can pick it up on the go and learn from online resources (which I'm doing a lot of myself these days!), then a degree may not be necessary. On the other hand, if you feel like you'd like the foundation a degree can provide, it could definitely be worthwhile.
torizhao's profile thumbnail
Thx so much for the thoughtful reply Jahna! This is really helpful for the transition I'm thinking about.
katreed's profile thumbnail
@jahnamcnamara great post! It's tough to find women in the startup space, and even better when we help each other by sharing our experiences. Maybe every woman in tech has read this book by now, but if not, Sarah Lacey's book, A Uterus Is A Feature Not A Bug is excellent. It was published in 2017, but she talks about starting a company while pregnant and you may enjoy it. Thank you for sharing your experiences, I experience them every day and appreciate you articulating the journey!
jahnamcnamara's profile thumbnail
Thank you so much @katreed -- really appreciate it! I completely agree with your sentiments, and it's so great to hear from another female startup founder. It's so important to be open about our experiences.I have not actually read that book so thanks for the suggestion. I'll definitely have to read -- sounds super interesting!
katreed's profile thumbnail
@jahnamcnamara the book is REALLY great. I am childfree by choice, but completely get how womxn are judged when they are pregnant and continue to work and build things. Take care!!
sydneydahl's profile thumbnail
Love everything you wrote about here @jahnamcnamara! I recently left my job to build my own startup in the pet industry and I have experienced many of the same things you describe. Thank you for sharing your experiences and journey. Rooting for you and Critter!
jahnamcnamara's profile thumbnail
Hey @sydneydahl, thanks so much for reading and for the comment! It’s really great to hear from another pet startup founder. I’m rooting for you and your company, too!