Need some motivation & advice after quitting a high paying job & failing on my startup

I left a high paying corporate job to start my own company.

It didn't succeed, but the reasons why I left were less about starting my own company and more about not feeling stagnant in what I was learning. I no longer wanted to feel like a cog in a large organization.

Even though the company didn't succeed financially, it succeeded in giving me satisfaction for learning things outside of my comfort zone, being comfortable taking risks, and have a clearer understanding of what motivates me. It also opened the door to many other rewarding opportunities.

After my startup failed I spent time working for TechStars in Boston and New York. I worked with founders, mentors, and investors to understand executing in the early stages of a company.

After TechStars I spent time developing products at early stage products as a freelancer. This opened up more opportunities to learn about how companies go from 0 to 1.

If I could offer some unsolicited advice, I would say you learned about your own strengths and limitations of building a company. You also probably learned a lot more things you probably wouldn't have had the opportunity to learn at a larger organization. While results of a company (in terms of revenue) are important, the journey is what is truly rewarding.

For me I know that I start losing interest when I no longer have agency over my own intellectual path. In a corporate environment that agency is most likely non-existent.

It's hard to not discount your efforts because they weren't successful, but I see a lot of people respected for giving it a try and failing. Don't be too hard on yourself and celebrate the small wins in the journey and learn from the things you weren't satisfied with.

You're conflicted in what you want.

You want the creativity to do your own thing, but you also want a cushy guaranteed salary. You're like somebody who wants the stability and companionship of marriage, while also desiring the independence and freedom of being a bachelor.

It hardly needs stating that you can't have your cake and eat it.

Going solo and starting a project from scratch has risks. You maximized these risks by working on the project full-time, instead of bootstrapping on weekend/off-hours - which is wiser.

You also mistook technical excellence at a Job, with the wider self-management and entrepreneurial skills required to make a project successful.

There may also be a larger problem, excuse the presumptuousness: but you appear entitled. You're like a a type of person, from a wealthy background, elite schooling and comfortable career: who has never experienced failure or disappointment.

You're problem isn't that you're starving or have no options it's: hey something I did didn't workout - how dare this happen to me! You're so used to having things your way, failure upsets your mental equilibrium.

I like what @alchemist said. Commitment to a path means full acceptance of what it may bring good or bad.

My comment is less to the author and more for other people in similar situations, including possibly my future self, since I just quit my job.

It's okay to feel a bit anxious about the future with all this uncertainty and moving pieces. It's pretty boring and limiting to know how everything will play out.

Maybe you have set unrealistic expectations. Your steady income came too "easy" for you for a long time, and you got used to it, but making money with your own project is a completely different thing. It is not easy and it is normal to take time.

6 months is a very short time to give up, but at the same time it is a really long time to stay building a product without validation. So lesson learned, validate faster next time. I recommend that you read the ConvertKit interview and also their article about when to Shutdown or Double Down. https://www.indiehackers.com/interview/the-story-of-convertkit-from-0-to-968-000-in-monthly-revenue-2fcb58f1fa

You need to know exactly why you quit and started this journey. Do you still want the same things? Or the status quo that your old job provided is more important?

Don't let your ego get in the way. Friends and family may look at you with the "you are making a mistake" eyes. But that's up to you to know.

Be careful because your brain will play tricks on you. It wants you to not change things, to stay in the comfort zone, where everything is safe and predictable. But that is usually not what we need to grow and to be really happy. Ask yourself: Was I comfortable or was I happy? Do I want to get back to that old path or this new one is worth pursuing?

I believe that you have really good savings. If you do, there is nothing to worry about now at only 6 months in. Give it more time, put in more effort. Try to make it work for real. Don't expect to succeed at your first (or second, or third) attempt. Keep trying multiple things, but in a shorter time. Optimize for quick learning and experimentation.

On the other hand, if you have already made up your mind that you really made a mistake following this path, it's totally fine to get back to where you were. Don't be too hard on yourself. Just make sure to listen to what YOU want, not what others expect from you.

Do you ever feel like you're missing out?
Do you ever regret quitting your job?

Those are definitely the wrong questions to ask. Are you just looking for confirmation?

It's easy for me to get a job but don't want to get another one because I don't think I'll ever find as easy going and as friendly environment as my previous job.

I recommend the book: "So Good They Can't Ignore You".

It sounds like you're still dealing with some regret about the old job and a sense of loss about the project not working out. You might be a little depressed, which would explain why it's hard to get excited about anything else. I think all of that's normal.

We all tend to push ourselves pretty hard here and set high goals for ourselves. That's generally good, but it's also good to let yourself off the hook when you need to. You don't have to feel great right now.

For what it's worth, I quit a pretty high-paying job about 8 years ago to start a company, and I failed miserably. It sucked, but although it's a cliche, I do feel like I learned some really core lessons. I mainly regretted being bad at entrepreneurship (I had zero experience), not the decision to quit. Now I'm earning a lot more than I was back in the day. I'm starting to dip my toes in bootstrapping waters on the side, and I wish I had gotten back to it earlier. But there are other plotlines in life, and those matter too.

I'd recommend spending a good amount of time reflecting on how things went and how your brain works. I like going for long walks, asking myself questions, and journaling about the answers. What was it that excited you so much about the project? Can you extract those qualities to search for them in your next job or project? It sounds like you're hung up on how easy and high-paying your old job was. Is that really what you want out of life? It doesn't sound like it, although I get that comparing yourself to your friends can be tough on the ego. If you were earning that much before, I think you should feel pretty confident that you can do well financially.

One more thought. Whatever you do next doesn't have to be the perfect gig. You could freelance, take a job, or work on someone else's startup even if it doesn't thrill you. Sometimes if you start acting like you're motivated, it can help you start to feel motivated. Or if not, it can give you one more data point on what really matters to you. It's ok to just put one foot in front of the other for now while you give your brain time to sort things out.

I, too, have a very unhealthy tendency to compare myself to others around me, which often leads to me feeling somehow inferior (I think this is the result of my upbringing/education, as I've always been encouraged to compete with everyone around me). I try to improve myself on this front every day, and one thing that always helps is reminding myself that I don't really know how others around me are really feeling; money is the easiest factor to compare because it's external, but how fulfilled are your friends who are still at their corporate jobs? Do they maybe wish they were taking a leap of faith and doing something they believed in? Not that you should wish your friends to be miserable, but just remind yourself that money and comfort are not the only things that matters, which is something you must have thought about when you were unhappy and making 250k/year.

Same boat. No remorse for me. Just got up and started looking for the next start up again, and still working on it. Why? Because I left my ego at the door when I walked in. .... "Fall down 7 times, get up 8." .... Are we done here?

Nobody said it was gonna be easy!

I was very passionate about an idea and spent ~6 months developing it while I had a very high paying

What was it that made you passionate to do this?

I'm curious what your goal is in starting a company?

Personally, my goal is financial independence. The simplest path to this is simply saving + compound interest -- so if I had a 250k job offer lying around, I'd probably take it.

Join a small startup and sweat your ass off to the top again!

"In 10 years, your friends might be doing very well, and you might be in a bad position, financially. Do you ever worry about your future? "

... really , you're worried about your friends and where they might be?

I'd suggest trying to change your mindset about your position in life. So your startup failed, who cares. Everyone thats succeeded in anything worthwhile failed MANY times over. Start another company. You might fail again. But eventually you will get a winner.

As for the job, if you can get a high paying job once , you can get it again.

To answer your questions:

• No.

• No.

• Work hard. Focus on goals that are 6 months out. (Because they are typically more concrete and actionable).

• You can't constantly compare yourself to others. That is way to be miserable. You don't know what problem other people have either.

Despite what it seems like all these overnight success stories, it usually takes a lot longer for any company/idea to find footing. 6 month in a startup life is just getting started. Even Slack, probably most recent super success story, seems like over night success. It was a struggling game company for a long time (and founder was already super successful from selling Flickr.).

Good luck on your journey.

Kudos to you for quitting your high-paying job and going all-in on your passion. Most people have too much fear, obligation, and debt to ever take that leap.

It feels like you let external factors define who you are. Money doesn't define you, although its hard to admit when everyone else is comfortable, I just realized I am different than my friends who can work 10 years in one company, earning good salary and let their brain rot. If that doesn't make you happy, why would you do it? You tried, you failed, you learned but at least you did something. Its all very hard and I personally failed on 2 companies before, going almost to zero net worth. I usually went back to work, stabilized my financial situation, got to know a lot of new people and industries and took the leap again. The worst part is just comparing yourself constantly to people who live in a different world, have different backgrounds and so forth. Of course we are all afraid that we might do worse in the future, but if you constantly compare yourself to others, you haven't figured out what is important to you. Therefore I suggest you dig deep in yourself and set what are your priorities? Being stable and earn lots of money? Or having freedom but risk a lot of what you have. Everyone's situation is different, but the only choice is up to you to make depending on the context.

What is your project? Maybe the messaging is wrong or you are targeting the wrong clients. Any business can succeed it just comes down to money, time, and will power.

Sounds like you want your easy high-paying job back but also don't like to work for someone else. Those are at odds with each other, and that could be contributing to your overall distress. Pick one of those things and just commit to that. It is important that you pick one thing, doesn't matter what that one thing is, and do that for a long enough time.

From the problem you described it's not that you have a money problem immediately. And what u were trying to do didn't work out like u imagined.

If going back to the same job is not an option the only next best time is to work with a startup that does what you like and joins for a low initial salary.

I feel that your issue as a wannabe founder is that, you lost the money from an easy job and you lost the passion for a tough project.

You need a sense of value from your present work, that best possible when your working on a project that u can relate too.

Go to the nearest co-working space, meet a lot of founder, share your story, see if you can work with them if needed for less than the normal, but make sure that the idea of that startup is something ur passionate abt or atleast care about.

For me this sounds like one of those hard times in life when the only choice is to keep going forward. Even if it's just one day at time. You might say that you don't know what direction to go to, but that's totally fine. You won't come up with the direction at this point as you are so deep in your thoughts. First you need to get out of there and that takes time. How long? Few months, a year - only you can find it out.

The best way to start feeling good again is to spend time with friends as much as you can. Be grateful for what you have instead of feeling sad for what you don't have (meditation and yoga has helped me with this). Take time to realise again how amazing life is and how lucky you are (man, I've never earned more than 20k a year) and the new direction comes naturally from there. Basically what I'm trying to say is that don't try to come up with answers when you're feeling like shit because they won't come. Make yourself feel better first.

You made a bold decision to quit your day job and you knew you are not taking the easy road. You wanted something more than a normal job in a big company and you were willing to take risks to follow your calling. Now you see in reality why it's not the easy road - it takes you to the limits of your abilities. The truth is that what ever you wanted from this road is still there. You can have those friendly people in your own company as well. You can definitely have it all if you just keep pushing through this phase. And that's what it is - just a difficult phase on the road to your success.

What kind of job was both that high-paying and easy with no overtime?

I'm curious what skills you have that enabled you to get such a cushy position (and believe you can easily get another albeit less pleasant one). Why does the job market value those skills so much while the broader market doesn't value what you can create with them?

I gave up a job that was well-paying, but where I felt stifled and like my brain was deteriorating from lack of challenge. Later, being broke caused me a lot of pain, but I've actually never regretted leaving or felt fear about the future as a result.

Hey man :)

So I'm definitely not the right person to give you tips right now since I haven't even really made half what you made in your life, not even a small part of it but I know the taste of being too passionate about something that it even blindfoldes you without even feeling it,

I've had this happening to me a couple of times before and the last time it caused me to never really getting to study what I want in college but something random I had 0 passion in.

I just really want you to know that its absolutely a human behavior and something that could happen to the best of us and beating yourself over it won't really help you at all, you shouldn't even wait for motivation to get back to your normal life or decide to start something new because motivation will always betray you when you need it, so just keep pushing through these shitty days and hope for the best.

Great luck brother / sister. 💛

Hi,

I'm a coach. And part of the requests I work with is to help people to return meaning into what they do. Would you be interested to explore how it can help you?