I planned for the money risk, not the constant doubt

★★ signal-medium r/entrepreneur · ↑ 220 · 💬 46 · 2026-01-22 · kw: better way to · open on reddit ↗

Tool

none

Issue

Founder experiences constant low-level anxiety and decision paralysis on side project, questioning pricing/timing/launch decisions multiple times daily with no external validation or mentorship, creating mental fatigue despite financial safety.

Cost

unstated

Recommendation

Talk to founders weekly for validation and guidance (JaimeYeung14); trust yourself and frame doubt as normal (CS--); use Getting Things Done (GTD) system to externalize tasks and reduce mental load (BusinessStrategist); find a North Star or mentor to reduce stress (Perseverance_ac)

extracted with

anthropic/claude-haiku-4.5 · 2026-05-08

Body

I started working on a small side project a few months ago with the idea that I’d slowly grow it and see where it goes. Nothing flashy, just something I thought could actually turn into a real business if I stayed consistent. I have some money saved up, so I wasn’t risking rent or groceries, which made me feel like I was being “responsible” about it. What I didn’t expect was how much mental energy it would take. Every decision feels heavier than it should. Pricing, timing, whether I should launch now or wait, whether I’m overthinking or underthinking. I’ll make a choice, feel okay about it for a few hours, then start questioning if it was the wrong move. There are nights where I’m sitting on the couch playing on myprize, not even working, but my brain is still stuck on the business. Wondering if I should’ve done something differently that day, or if I’m already messing it up without realizing it. It’s not burnout exactly, more like this constant low-level pressure. The funny part is, when I talk to friends, they think it’s exciting. And it is, sometimes. But a lot of it just feels lonely and uncertain in a way I didn’t really anticipate. There’s no one to tell you “yes, this is correct” or “no, that’s a bad idea.” For those of you who’ve been doing this longer, does that part ever get quieter or do you just get better at living with the uncertainty and trusting your own decisions?

Top comments (9)

[score=1] AutoModerator

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[score=17] JaimeYeung14

It’s lonely when you are working on something without any guideline. Friends think it’s exciting because they’re not the one making 50 decisions a day..If you can, talk to a couple founders each week, even just a quick call. It helps a lot since they’ve been in the same shoes.

[score=11] kozer1986

I feel you. I'm in the same position. Really interested for the responses here.

[score=12] -CS--

You just get better at trusting yourself. You have to understand early on that there WILL be no one to validate your decisions in most cases because that’s the entire point of entrepreneurship. Don’t take this the wrong way, it’s always better to work with people, learn from others, and offload certain responsibilities to others, but at the end of the day you are trusting yourself to be better than anyone else - that’s why you started, and that’s how you continue. It’s abnormal not to doubt yourself. It’s always on you. Frame it as a good thing. If you didn’t think you could pull it off you wouldn’t have started. Trust yourself.

[score=12] [deleted]

[removed]

[score=6] Familiar-Jeweler6510

it is hard because all of our childhood and school years we were trained to follow someone else's orders , get tasks and do them how they ordered entrepreneurship is way way different than this and the exact opposite even the greatest founders and business men said that in the earky process they didnt know what they were doing either just acted and hoped for the best you are not alone bro , everyone is like this especially at the end the more you are doing it , the more you will trust your decisions more and you will learn from it everytime and do better the next.it is simple as that. you just have to do enough reps in this no one has it a figured out and everyone is questioning keep going

[score=3] BusinessStrategist

Have you mapped out your journey? You stated a "desired outcome" which is to complete s "small side project." What is the "due date" of this "milestone?" Have you broken down your project into specific linked tasks? Have you planned for tasks, resources, and people to complete the work? Do you have a GANTT chart to monitor your progress? Can you give us a list of "the gaps you need to fill" and the "obstacles" that you need to overcome to reach YOUR destination? If not, what's holding you back. Make a WRITTEN list of the specific roadblocks. As for the "mental soup" that is feeding your anxiety. Google "Getting Things Done (GTD)." You want to capture IN WRITING all the tasks that you've identified and dump them into your GTD hopper. Go through the list and sort them into your 'prioritization" folders. The process is very simple and there are many apps that simplify the work of planning and executing the work that needs to be done. Many of the GTD apps also provide a visual GANTT view of your project. Now that you've taken some control of your work. It time to think about listening to your biochemical machine made up of body and mind. Emotions are the "dashboard engine lights" of your biochemical machine. If you give it the right fuel, perform regular maintenance, AND look into those engine lights, you'll discover that your mind is loaded with reminders, due dates, deadline dates, don't forget this, don't forget that, etc. Your "dashboard engine light" is alerting you that you're not in control of your actions. Stress increases to anxiety, to fear, to panic and finally to "Fight or Flea." You might try to adopt a new routine that involves capturing all those reminders and other tidbits of info in your GTD app. That way you won't wake up at 3:25 AM asking yourself if you forgot to... And, at the end of every day, PLAN YOUR NEXT DAY. That way, the next day will be an exercise in getting the important stuff done. And don't forget to include some "timeout" slots to let your engine cool down. Google "Pomodoro timer" and how it helps your brain reach maximum performance without turning into a big pile of discouraging spaghetti. Plan your work AND work your plan. ALWAYS CAPTURE YOUR PLAN in WRITING! That's how your mind will know that you're serious about keep Me, Myself, and I safe from the Sabertooth tigers.

[score=3] Perseverance_ac

Oh man, this is the main pain for all founders, even if they don't say so. And then success comes: you have your first paid customer, you think the pressure should lessen, but no. The growth is the next bottleneck, then trying to raise, then if you raise - you actually now get even more stressed out, because now you are responsible towards investors, not just yourself, and then you need to raise again.. It's just a constant stress and that's why many people break and return to having a day job. I was asked multiple times "why do you need this at all, get a job at a big corp". My answer is: "do this only if you have a North Star" otherwise if you are doin this for money, it just makes no sense, and you can make more by having a normal job.

[score=2] Jolly_Paramedic4434

Welcome to Owner life. There is always work and another thing to do. It's not easy, but it's worth it! It's a different mindset from being employed, and it's not for everyone, but you can learn how to scope your to-dos into reasonable schedule. Also, get help to make your schedule lighter, but most importantly - allow you to keep on growing up your business.