Working for yourself is an aspiration many of us hold as a life goal. It feels liberating. But like most things in life, the aspiration is sometimes only the tip of the reality iceberg.
We wanted to create an objective list of what employing yourself looks and feels like, versus a list of Instagram memes about how to get off the corporate treadmill and make a million in crypto.
It may not be sexy, but here’s what a number of us have learned along the way:
It requires you to be very resourceful. Gone are the days of expense accounts, HR, finance, budgets, legal teams, or any form of admin support. If you want a crash course in being scrappy, this is it.
You learn the true value of networks and relationships. Once you have no employer calling card, all you have is your reputation and your relationships. It’s a reminder to treat people well throughout every step of your career journey.
You still answer to someone. The idea that you no longer have a boss when you work for yourself, is a myth. You still answer to clients, customers, investors, family, or friends. The difference is, they don’t gate-keep your day like a boss might.
You have to buy the things you took for granted. Paper, pens, travel, insurance, benefits, laptops, phones…and say goodbye to bonuses. Your relationship with money changes - because it’s your money. You quickly weaponize frugality; and have a sudden awareness of how much the business world has been overcharging you all these years.
Your definition of team changes. You move from being directed to being self-directed. It can feel liberating for sure - but also lonely. You no longer have a boss or colleague to bounce ideas off. Google and Wikipedia become your new teammates when trying to find answers to stuff you thought you knew.
You might not get paid. Everyone we know who works for themselves has at some point, not been paid by a client. It’s a fact of life. Not every frog you kiss becomes a prince or princess. Some stay frogs.
Shedding your skin and letting go. You become valued for your specific skills, not the expectations of a corporate job description that anyone can slide into, or a culture that demands you operate in a certain way. Dropping those old expectations can feel strange.
There are no real politics. You are no longer in an ever-narrowing funnel of competition for opportunities above you; the funnel is completely the opposite. It’s now as wide, bright, and welcoming as you want to make it.
You have a real bias for action. Gone are the days of switching off your camera and putting it on mute during a meeting. Meetings need to work. Emails need to be answered. Decisions must drive forward movement. You become very, very aware of your role in guiding action, and the consequences of when something doesn’t happen.
It takes so much longer. It’s unlikely to all happen overnight. It takes about three years to get your own business going. A year to figure it all out and plan, a year to get traction, and then a year where it all seems to come together. There’s some nifty magic at work around year three that none of us can explain.
One thing we all agree though; you don’t need to work for yourself to have a great job, find purpose, and have a fulfilling career. But the skills you use and learn when you do step off the traditional job ladder, can enhance your market value in ways you may never have appreciated.
It’s for this reason that we gravitate to those who’ve both tried and succeeded or tried and failed - it doesn’t matter. What matters is that you’ve proven you have the confidence, grit, and resilience to try, and that’s a skill set that’s hard to find elsewhere.