How To Hit Every Difficult Entrepreneur Milestone

Every business owner is working towards something on a 5–10 year timeline. It looks different for every person, but it’s usually some kind of milestone that requires scheming and heavy lifting stretched over a span of years.

These milestones are h-a-r-d to tackle. They come with puzzles, twists and bends you didn’t anticipate, and a healthy number of hard moments that entice you to quit.

Here are some of the milestones you may currently be chasing and how to meaningfully pursue them.

Exponential growth

This is the most popular milestone we chase — traction that shows that our business is legit or that it has unicorn blood in its veins.

The most common mistake I see business owners make when they’re chasing this milestone is functioning as if their product’s features / tastiness / beauty etc. will be enough of a sell. It’s not. Products sell when it’s powered with social capital or sweat equity behind it.

Those online brands that are selling hundreds of units a day? They are diligent at protecting and growing their social capital online through meaningful interaction and engagement. My partner sold his beverage brand to a publicly-traded company, but it took him years of sweat, schmoozing retailers, and doing demos in grocery stores for an ungodly number of hours to get there.

Don’t mistake work you don’t see happening under the hood as work that’s not being done at all. Behind every exponential growth story is someone knocking on doors and messaging customers 100x more than the normal business owner would. If you want to be an exponential growth success story, put in the work.

Sell the company

Walking away with a fat paycheck after selling your company is an exit all entrepreneurs entertain.

However, this is not an option that’s granted after you hit a certain number of years of operation or once you’re ready to retire. You need to intentionally build up your business’ most coveted assets to make it sales worthy.

If you think that there’s a possibility that you may sell your company one day, reflect on the palpable asset you would sell to your buyer. What’s that juicy asset you’ve built after 5–10 years of company-building that a buyer who wants to enter your industry would be dumb not to buy?

Is it the number of celebrities clients that are associated with your brand (aka your brand reputation)? Is it the trade secrets you’ve gathered from creating and selling multiple bestselling products in your industry? Is it a course or program that has helped transform the lives of thousands of customers?

Figure out what your most sellable asset is and build it up until it looks like the best in show.

Impact

Whether it’s making a positive impact on the environment, giving back to charity, or molding the world into one you want to live in, making an impact is a huge driver for many entrepreneurs.

This is an interesting milestone where I’ve observed the heaviest feelings of unworthiness and not-enoughness. When your milestone goals swim within the context of big, hairy problems like climate change, poverty, or the gender wage gap, the entrepreneurs who chase this milestone usually feel like what they contribute is not enough even after years of donating and supporting important causes.

I don’t have an answer on how not to feel like the impact you make on the world is not enough — this is an existential question I still am in search of understanding. What I can say though is that the kindest thing you can do for yourself and the cause you want to support is to set goals and intentions that are easy to commit to. Overpromising and failing to hit lofty goals usually lead to defeatist mentalities that make doing good feel like crap.

Slow and steady makes the most impact over time — set achievable goals and hit them consistently so that in a few years time, the impact you’ve made is meaningful.

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

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