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In business, as in life, there are ups and downs, and oftentimes they come out of nowhere and blindside you, instilling doubt or confusion where there used to be certainty. In the startup world this is called the Trough of Sorrow- a period of time in which the founders lose their way while seeking product market fit. While the term originated in tech, it applies to startups across industries, and most certainly has applied in my journey founding Swig + Swallow.

 

In my experience founding Swig + Swallow, getting in and out of the Trough has been 100% psychological. What I’m about to say may sound counterintuitive, but I believe there’s always a way to manage real constraints. Don’t have enough product? You can make more or run out for a while. Need content, but don’t have a content team? Learn how to make it yourself. Need to fulfill a big order but don’t have the money to do so? Get PO financing, take on a loan, take on investment, etc. Of course there are unpredictable situations that can sideline or bankrupt a business, but the overwhelming issues faced on a day to day- at least with our business- have been manageable with some (sometimes a lot of) creativity.

 

When there are clear constraints, it’s easier to see clear steps forward.

 

The worst Trough of Sorrow moments for me have been when everything about the business seems “normal." Maybe you had an off day, week, or month, but there are no critical differences in the business. One day you wake up, and for some reason, you just feel different. Yesterday you were killing it, running at a million miles an hour, rainbows followed you everywhere, and the favor of the gods shone upon you. Today you wake up and objectively, little has changed, but you feel grey, stale, flat….like you're moving backwards, or just generally confused about your direction. In my experience, this hasn’t been a single stretch of weeks or months, but has cropped up 3 or so times for days to weeks, in the course of the past 2 years. For me, it’s easiest to slide into the Trough when there’s an abrupt change of pace with my workflow. I’ve always found that it’s easy to prioritize when you’re super busy, because you have to be ruthless about what to address first. When all the sudden you have more time on your hands, it’s harder to determine the next critical step, and it’s easy to lose focus. 

 

These are the most dangerous times, because your emotional brain is devious, and will make you doubt everything about your idea, your capabilities, and your choice to take risk in the first place. Basically in these moments your emotional brain is like your closest loved ones- they’re looking out for your needs for food, safety, and shelter, and as such, they’d rather see you throw in the towel and get a desk job with a pension, than stick it out, struggle, and create something amazing that the world has never seen.

The solutions and supports I’ve put into place and used each time this happens have been incredibly simple, and have pulled me out every time. I’m bulleting them below for easy reading.

 

  • Exercise/Have a life Outside of the Business: I’m sure some onlookers have some choice things to say about how public I am with my recreation (most of my personal instagram feed is about rockclimbing, dancing, learning musical instruments, etc), but this is very intentional- it’s not a distraction. Burnout happens when you feel unbalanced, or when you’re making unsustainable sacrifices to reach short or medium term goals. I try to exercise every day- even if it’s for 15 minutes- so I can go to sleep and wake up the next day feeling like a whole person. The endorphins are nothing to sneeze at, and varying things up where some exercise is solitary (eg running on a treadmill) and some is social (like rockclimbing) has been key for me to fill in the gaps where I need it. Having a hobby or interest that is entirely distinct from your business is key too. At times your brain becomes fatigued from focusing on the same issues over and over, and it’s been most fruitful (for me anyway) to take a break and exercise a different part of my brain, before returning inspired and refreshed.
     
  • Keep a Journal: Journaling is amazing, and allows you to translate an abstract emotion (I feel shitty) into actionable data (I feel shitty because of X). If you feel shitty because of a specific situation with the business, you can then outline how to address that specific problem, and take action. If you start writing and realize you just feel shitty because you feel shitty, then you have it on paper in front of you, and your logical brain has an opportunity to speak up and fight back. In my case, occasionally I’ll wake up feeling demoralized about the business, and realize it’s because I slept or was eating poorly, or I had forgotten to pay a parking ticket for weeks and it was lurking in the back of my brain bothering me. It may sound trivial, but the more quickly you can get to the root of the malaise, the easier it is to resolve it and move forward. **One additional benefit of journaling is that it creates an indisputable trail of where you’ve been, and it shows you that you (yes you!) can climb your way out of it. No matter how bad things have been before, you overcame, and here you are today, ready to face your next challenge.
     
  • Listen to, Watch, or Read Stories about Successful Entrepreneurs: I ingest a lot of media on founding, running, and growing startups. I drive a lot, so I’m always listening to a podcasts. How I Built This, and Masters of Scale are my two favorites to play on repeat. They’re very different formats, but I use them to stay inspired every single day. They highlight either full biographical stories, (HIBT) or insights and learnings from incredibly successful entrepreneurs (MOS). In all of these cases, had you spoken to the entrepreneurs when they were first eking things out, they probably would have been stressed, frazzled, and uncertain- but looking back on their struggles and eventual success, it’s easier to visualize your own inevitable success. 
     
  • Surround Yourself with Other Entrepreneurs: This is an invaluable learning I realized very late in the game. For probably the first year we ran Swig + Swallow, I had clustered socializing with other entrepreneurs in the same bucket as formal “networking,” (which I find to be a distraction from “doing my job", and most often a complete waste of time.) What I hadn’t quite realized was that while entrepreneurs may have the least to give in terms of time or resources, in general, they're the most generous and supportive group of people, especially towards other entrepreneurs. Unlike your average consumer, they started their businesses because they saw a problem or opportunity, and have a bias towards action. They want their businesses to work, and they want your business to work, full stop, so they’ll give you that tough feedback, but with the intention of helping you overcome your problems.

    About a month and a half ago I pitched Swig + Swallow to investors on The Pitch podcast (they have about 100,000 listeners internationally,) and the outpouring of support from other entrepreneurs across industries from around the globe has been overwhelming. On the day to day, I can’t tell you how generous all of my kindred entrepreneurs have been in the NY food community. Being able to hear their stories, be inspired by them, and commiserate over shared experiences makes you realize we can ask for help when we’re weak, give help when we’re strong, and together we can take over the world. 

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