Your Business Is Not That Into You

When to quit and when to stay — what to do if you’re having second thoughts about keeping your business.

Sophia Sunwoo
5 min readJun 18, 2021
Photo by Annie Spratt

It’s hard to know when to call it quits on your business.

Whether your business is extremely stressful to manage or sales aren’t taking off at the level you’d like it to, you may be thinking about calling it quits and whether it’s the right move to make.

When you’ve put a tremendous amount of time and effort into building a business, your ability to pinpoint when it’s time to tap out becomes foggy because your emotions add heaviness around leaving.

So it gets hard to call it. It becomes difficult to balance your heart’s opinions from your brain’s, and an internal struggle develops that clouds up what to do next.

If you’re in this tough spot, here are some common blocks and questions that you’re likely entertaining right now and how to sort through them to help you find clarity around staying or letting go of your business.

The investment of not quitting is too high for you

What would it cost you to stay and make your business a booming success? Would you need to make a large capital investment in hires, tools, and launch a marketing blitz with the budget to pair it with?

In addition to the cost, what kind of energy and time investment would it require from you to make this all happen? Do you have the excitement and drive to revive your business towards growth?

If it costs you too much financially, energetically, and time-wise to not quit and continue running your business, it’s a pretty solid sign that you shouldn’t keep going. However, if your heart’s in it, and none of these costs intimidate or challenge you one bit, consider this your temperature check that you should keep going.

You don’t want to entertain it as a side hustle

If you’re not thrilled with the idea of injecting more capital into your business in order to increase revenue, can you entertain your business as a side hustle while pursuing other interests that you are stoked on investing more time and energy into?

If your business can be run at a somewhat passive level and still generate revenue for you, it’s entirely possible that you can keep things as is while pursuing another journey.

If even the idea of entertaining your business as a side hustle is mentally taxing for you, this is a sign that your business is not worth keeping alive. Financial currency is not the only currency that matters when it comes to measuring the viability of keeping a business alive — your mental peace of mind and intellectual happiness should also be calculated at the same level, if not more than the financial payout.

If your business feels more like a chore, rather than something that’s feeding your soul and inspiring you on the daily — then you’ve started a business to do work you don’t love, working for a boss that won’t let you quit. Sounds terrible right? Be a better boss and do yourself the favor of firing yourself if you’re working out of obligation, not passion.

Your only reason for staying is because of investment guilt

If the top objection that comes to mind when you’re thinking about leaving your business is guilt because you’ve invested so much into the business already— that is not a good enough reason to stay. Staying with a business because you’ve invested so much and you’ve come too far is similar to keeping investment in a long-held stock even though it’s plummeting in value every single day (with no sign of bouncing back).

Whether you realize it or not, you are initiating a death by a thousand cuts scenario the longer you stay mentally and financially invested in a business that’s no longer lighting you up. If you’re guilt-ridden about abandoning a business you’ve spent so much time building, think about the time, energy, and money you’re leaking through your indecisiveness — you are splitting your energy in two different directions (growing and dismantling) rather than directing all of it towards growing.

Your strategy is great and your business is still not that into you

Not many entrepreneurs talk about this one, but I think that it’s a crux that more need to acknowledge. Sometimes you do all the right things like hire a brilliant business consultant, deploy a top-notch marketing and sales plan, invest in a lot of solid plays and yet, nothing catches on fire. It starts to feel like your business isn’t that into you, and that you’re on one end constantly giving and investing, without your business reciprocating any kind of meaningful interest or return.

I can’t speak to your individual situation without talking to you 1:1, but if you’ve invested in the right support and expertise and are still falling short, it may be time to consider that the stars aren’t aligning for you.

Whether you’re destined to do something else, the timing isn’t quite right, or a myriad of other factors aren’t rallying behind you — this is a valid tension point that in my opinion, is enough to call a pause or closing. At the end of the day, building any type of business is going to be hard, but it’s a question of the type of hard you want to hammer away at.

I prefer choosing the type of hard that simultaneously brings me joy while I’m working on it, where there’s some ease to how everything flows and unravels. I don’t want to work on the type of hard that fights me at every corner and doesn’t reciprocate any of my interests. This logic isn’t business strategy, but just a call out to the existence of masochistic hustle culture amongst entrepreneurs, and that its presence is very real.

Sometimes hustle is great and needed, and other times it’s destructive to pursue because it leads you towards an uphill battle you don’t have to entertain. Decide on the type of hard you want to get behind.

For more content like this that turns your startup chase into a victory lap, get my Friday morning emails, (lovingly called The Crux) in your inbox.

--

--

Sophia Sunwoo

I create moneymaking brands with womxn entrepreneurs who refuse to settle for mediocre. www.ascent-strategy.com