Four Things I Wish I Knew Before Going Independent

After a few months at my very first job working at a broasted chicken shack, I knew I didn’t want to spend the rest of my career working for others. A few marketing jobs, a stint at an interactive agency and loads of stress later, I finally made the leap. When I first became a solopreneur, I was both excited and terrified — at the same time. Though I'd been planning to leave my job, a layoff hastened my first business venture. I had no idea what I was doing other than the fact that I wanted to work for myself. I learned so many things the really hard way.  I mean like pushing an elephant up a hill — and you’re in the elephant’s butt.

When you become a solopreneur, you bet on yourself. Here are four things I wish I knew during my early years as an independent that would have made it easier.

1) How to manage instability

Traditional jobs offer a level of stability that can be hard to come by for solopreneurs — especially in the early years. When I went on my own, I knew there would be instability, but I wasn’t prepared for how wide the swings would be, or how long they’d last (years rather than months). Some months I far exceeded my projections while others months the number was far lower, even $0 at times. At first, I thought I was just a failure. Then I realized that just about every solopreneur experiences income instability.

Coming up with projections for your business is smart, but you can’t treat those projections as a budget. Income variability made budgeting tough, especially when it came to paying taxes or putting money into a personal savings account.

What I wish I knew:

  • Set aside 30% of each client payment for taxes.
  • Create an automated payment from your checking into your savings account. While it can be tough to put big amounts away especially when you don’t know how much you’ll earn in the coming months, you won't miss small amounts. Start with a small amount; it will add up without you noticing or feeling like you’re depriving yourself. When you're able, stock away more money for those lean months.

2) You will be rejected

When I started my first business, it didn’t take much to rattle me, especially when it came to selling myself. Even though I’d been around sales and marketing in my traditional job, it was the first time I had to promote myself rather than some other product or service. Terrified of being rejected, I struggled with asking for the business outside my network of friends. You know the result, my business grew slower than it should have because of my fears. Eventually, I got desperate and developed a thicker skin, but I wasted a bunch of time. Today when a prospect doesn’t say yes, I don’t even flinch, I simply move on to the next priority in my business.

What I wish I knew:

If you want to have a sustainable business, you have to learn to sell to strangers, and that means learning how to deal with rejection. And, I wish the Rejection Therapy game had been around. The Rejection Therapy game is simple: get rejected by one person every day. While this may seem like a masochistic exercise akin to walking on coals, it can be a life changer for folks who must sell themselves but live in fear of rejection.

While there’s an actual Rejection Therapy game you can purchase, you don’t need to buy it to play the game. Just commit to a period where you ask strangers for something. Start with 30 days where you actively look for opportunities to be rejected. If you start shaking at the thought, just start with a week. If you’re a total rejection novice as I was, begin with small asks, working your way up to bigger ones as you go. The goal isn’t to get a yes (though you will sometimes), it’s become more comfortable with the feeling of being rejected. When you take the sting away, it makes it easier to ask for what you want, which is so important for solpreneurs.

3) No business owner has it all together

I failed a whole bunch in my first few years. I hired a marketing consultant who did nothing except prepare a 50-page report with no actionable items to promote myself to my target market. I suffered through TurboTax for years, waiting too long to hire a good accountant to do my taxes. I low-balled my rates and even once accepted brownies as part of my payment. I wish I was being facetious about that last one. Every time I made a mistake, I chastised myself for getting it wrong. I even started to believe I just wasn’t good at running a business. I even considered going back to work for someone else. Luckily, I fell in with a group of other solopreneurs who shared their foibles. I kept making mistakes, but I no longer gave myself a hard time about it.

It’s easy to put a shiny veneer on your life these days, isn’t it? Instagram, Twitter, and blogging make it easy to craft an image that we want others to see. Business owners are no different. As solopreneurs, we create the myth that we have it all together and that we never make mistakes. That we pay our taxes on time, price ourselves appropriately and always have a waiting list of clients.  Part of the problem is that we compare ourselves to those thought leaders who’ve been in business for a decade or more. But that’s inaccurate comparison. It’s not that they didn’t make mistakes — they made plenty of errors, many probably the same as you. They’ve just had much more time to figure it out. And here’s a secret, they still make plenty of errors.

What I wish I knew:

You will make mistakes. Everyone does. Don’t linger on your failures, fix them, learn from those mistakes and move on. Also, never compare your business (or yourself) to anyone else. You have your own path in life and in your work. Rather than compare yourself to others, compare yourself to last year you.

Focus on what’s going well. The best thing I ever did was to make a list of acknowledgments every day. Focusing on what I did right helped me focus on what was going well rather than everything I did wrong. It also gave me a confidence boost.

4) You can't do it all alone

Lone wolf. Independent. A healthy fear of authority. Do any of those words describe you? They described me when I went out on my own. My guess is many if not most solopreneurs prize being their own boss. They chose their business type because they don’t want to report to anyone — or have anyone report to them. This same independence though can be limiting.

In the beginning, I bootstrapped my business from nothing. I went out on my own for the first time in the middle of a downturn after being laid off which meant I had a little runway. My budget margins were razor-thin. One time, during a particularly hard month waiting for client checks to come in, I had $13 in my checking account.

Not having much extra money to invest in my business meant that I did everything myself rather than getting help through a bookkeeper or virtual assistant. I used Turbo Tax long after I should have hired an accountant. Even when I started making plenty of money to afford them, I took on all tasks myself for far too long. I was working too much, I didn’t have the expertise I needed, and so I made mistakes. I didn’t talk with other solopreneurs enough. My hard-won self-reliance became a liability.

What I wish I knew:

Even though it’s your business, you can’t do it all on your own. To bet on yourself, you're going to need help sometimes. For support, find a group of other solopreneurs. Identify a mentor or hire a business coach. And as soon as you can afford it, hire a virtual assistant, a bookkeeper and the best tax accountant you can afford. It will be the best money you've ever spent.

Those are just four of the things I wish I knew before starting my business. How about you? What do you wish you knew? I’d love to hear yours.