How do I know if I should sell my business?
Selling a business often means choosing between the relief of walking away from burnout and the fear of regretting walking away right before it pays off. Emotional involvement makes it nearly impossible to see the situation clearly, especially when balancing inconsistent income against the prospect of managing a team or handing off five years of hard work.
What the numbers show
Counted from the threads quoted below. How we count
- People have been saying this in most months since July 2026.
- This comes up 22.2× more often in r/smallbusiness than across the site as a whole.
What people tried
Every workaround mentioned in the threads below. We haven’t tested any of them — and nobody here is claiming they worked.
Found another way around this?
Share your steps and trade-offs so fellow engineers don't have to reinvent the wheel. No account required.
- 1Selling a 50 percent stake with an earn-outDid this help you?
- 2Asking for a higher valuationDid this help you?
- 3Replacing oneself and keeping the cash flow goingDid this help you?
- 4dissolving or sunsetting the business instead of selling itDid this help you?
- 5pivoting focus to a new venture like online live sellingDid this help you?
- 6applying for jobs on the side to gain financial stabilityDid this help you?
- 7relying solely on word of mouth advertisingDid this help you?
- 8Doing freelance work and comic cons to keep things goingDid this help you?
- 9Evaluating what percentage of overall net worth the stock represents and considering whether to reinvest in index funds.Did this help you?
- 10Using the thought experiment of whether one would buy the stock today if holding cash instead.Did this help you?
- 11Evaluating debt payoff amounts against potential future earningsDid this help you?
- 12Consulting online forums for external perspectives on partnership buyoutsDid this help you?
- 13continuing to run the business independentlyDid this help you?
- 14hiring professionals and technicians for outsourced tasksDid this help you?
- 15trying to work out whether the store is genuinely viable as a standalone businessDid this help you?
- 16operating under a self-imposed scarcity economy by selling alternative items when bestsellers cannot be reorderedDid this help you?
- 17ignoring instructions to avoid discussing the risk of insolvency in management meetingsDid this help you?
- 18Holding the stock long-term without paying attention to itDid this help you?
- 19Selling shares that qualify for long-term capital gains while keeping othersDid this help you?
- 20Reinvesting proceeds into a high-yield savings account or total market index fundsDid this help you?
- 21Treating the decision as if deciding whether to newly purchase the stock with cashDid this help you?
In their words
Unedited, grouped by where they were said, most upvoted first within each place, each linked to the thread it came from.
“I keep going back and forth between "take the bag, you're 28, you have time to build something else" and "you built the thing that's about to work, don't hand it off right before it pays off."”source ↗
“He's been trying to sell for years now, but he lives in the VERY rural Midwest and isn't very tech-savvy so I'm pretty sure word of mouth is the only way he's advertised it.”source ↗
“Because of his remoteness, the buyer pool for a business like this is tiny.”source ↗
“The part I’m struggling with is the potential upside. We built this thing from nothing and I’d hate to sell for $70k and watch it become worth a shitload more a few years from now.”source ↗
“The problem is the two partnerships aren’t guaranteed long term and the subscription side is still really new, so I have no idea how sustainable any of it is.”source ↗
“I actually want to stay and help save the whole company, but I am seriously considering buying Store B out before the wider group drags it down with it.”source ↗
“My core question is whether B is genuinely viable as a standalone business once internal cash transfers, merchandise movements and artificially restricted reordering are properly adjusted for.”source ↗
“I’m looking for some outside perspective because I feel like I’m too emotionally involved in this situation to see it clearly.”source ↗
“Right now, the business isn’t consistently bringing in enough for me to comfortably cover expenses and pay myself.”source ↗
“After five years, I’m burnt out. I do everything myself, and I’ve realized I don’t have an interest in hiring employees or managing a team.”source ↗
“I’m now wondering whether I should try to sell the body contouring business as an asset or turnkey sale. I honestly don’t even know how realistic selling a business like mine is or what someone would pay for it.”source ↗
“Part of me worries that I’ll sell it and regret walking away from something I spent five years building. But another part of me feels like there could be a huge sense of relief in finally letting it go and allowing myself to move on.”source ↗
“I would still like advice on these particular numbers, largely because I still feel unsure about if I am somehow being a blind fool for even considering this.”source ↗
“The problem is that I individually have no experience in a commercial print shop, and frankly I have less than 7k to my name at the moment.”source ↗
“I feel so on the fence about the whole thing, largely because my personal finances aren't spectacular.”source ↗
“I’ve been split on whether I should sell the business”source ↗
“How is it that I should calculate what my business is worth?”source ↗
“What factors are to be weighed in before selling it vs keeping for a bit longer?”source ↗
“Put about 4.25 lakh into a surgical/hospital consumables wholesale business earlier this year - license, shop, stock, the works.”source ↗
“Pitched a bunch of hospitals and clinics; almost no one was interested.”source ↗
“Feels like I'm underpowered on both fronts that actually matter here.”source ↗
“Genuinely torn between pushing a bit longer vs cutting losses now.”source ↗
“It will take around 1-2 year to establish the connections and i have limited funds to operate the business forward”source ↗
“I have limited funds left to provide credit and stock rotation”source ↗
“I find myself in a place where I'm trying to decide if I should sell it back to the company or keep it.”source ↗
“If you think the stock will go up then keep them If you think the stock will remain comparatively constant then sell the long term capital gain one otherwise yes, sell it all”source ↗
“Would you buy them? If no, then sell and invest somewhere else.”source ↗
“If these are all the stocks you own I would swap (sell) half for a total market index fund.”source ↗
Where this came up
People with this problem also raised
- 19Should I keep going with my stagnating business or quit?
- 11How to decide if we should sell our house first?
- 15Should I sell my paid off car to invest the cash?
- 16Should I register a business before making any money?
- 4How do you sell a minority share in an unprofitable small business?
- 11Should I sell my farmland or keep renting it out?