Whether you're looking to move on from a business, a job, a relationship a geography or anything else, knowing when to move on is a tough decision. Even when things are perceived to be going well from the outside, your internal voice may be whispering that there is something different to be doing.
I've heard this question asked and asked this question myself many times in my life and I've never heard a great answer. Most answers are very general and lack specificity to be helpful. Understanding each situation is unique, I still always wanted a framework for how think about it.
After many years (on and off) thinking about this question, this is where I've landed - three questions to ask yourself.
Are you doing / in this because you genuinely want to, and it gives you life? Or are you doing it out of necessity (have to) —whether for money, ego, or opportunity? The reason behind your pursuit matters because your tolerance for pain will vary depending on your motivation. If you're passionate about what you're doing, you'll likely withstand more hardship. But if you're driven by external pressures, your endurance may wane more quickly.
Example - you've found yourself in a tough spot with a business you own / run. Did you start the business becuase it was opportunistic or did you start it because it's something you have a passion for and care deeply about the problem the business is problem. If your answer is b. then you're more likely to tolerate the discomfort required to build something meaninful and not let is ruin your entire mood and change your view of the world.
If you answered a. then that discomfort with actually feel "worse" and more intense and will bleed in to all aspects of your life. The reason you're doing something matters, so understanding why you chose to do something can help determine if you should continue doing it.
Evaluate the costs. This could mean money, time, relationships, or missed opportunities elsewhere. If the cost becomes too high—meaning you're unwilling to accept the tradeoffs—then it's time to reconsider. Are you sacrificing your health, personal relationships, or other opportunities for a situation that's not paying off? Weigh these factors carefully.
Again, doing any meaningful will cost you something, there is no other way. The question is what is it costing and are you ok with those costs?
As an example, maybe work is taking too much time from your family. Maybe that's ok because the upside is worth it. Maybe it's not ok because the no upside is worth the relationship with your family. It's your decision and it's personal, but getting very specific about what you're giving up to be doing what you're doing helps bring clarity to the situation.
This, for me, is the most tactical of the three questions. The beginning of anything is notoriously tough. However, if you've moved past the initial year and find yourself in a six-month stretch where nothing about the situation is enjoyable—be it the people, the product, the industry, or the day-to-day tasks—it might be time to move on. If there's no longer any aspect that brings you joy or satisfaction, this is a significant indicator that you should consider other options.
Dealing with pain and discomfort is part of life, but it shouldn't be all of life. If you've arrived in a situation that feels like all suffereing all the time, it's probably best to explore moving on. At that point, what you're sacraficing most is you're mental well being and is anything really worth that?
Every situation is unique, and everyone's pain tolerance differs, but framework for thinking about this decision is crucial. Without it, you could spend years on something you should have stopped a long time ago.
If you're comfortable with your answers to these questions, then keep going. It's supposed to be hard, and that's normal. But if these questions reveal significant concerns, it might be time to consider moving on.
Remember, moving on isn't a sign of failure. It's a strategic decision to open yourself up to new opportunities and situation that might be a better fit for your passion and talents.