The first time, I might have changed a few things. The second time, I had a much better plan of attack and an idea of what I was getting myself into. Both times, it took lots of deep breaths, some curse words, a good dose of fear and a rather giant leap of faith. Here’s a few of the bits I’ve learned along the way.
Don’t quit angry.
I did that the first time. I had a manager that, even from a more objective point of view many years later, was terrible. She wasn’t a leader, she didn’t really have any grasp over what I or my team did, and she was difficult and condescending on her best days.
The problem is that I let her get the better of me, and I left a chunk of my professionalism on the floor the day I quit. I marched in and resigned my job on the spot on a Friday. I didn’t give much notice, I was angry, and I expressed as much. In retrospect, my anger didn’t change anything. Sure, it was a great pressure relief valve…for about ten minutes. Then I felt a bit silly and temperamental, and it wasn’t likely I was going to repair the bridge I’d just very deliberately burned.
This isn’t even about “preserving references” or some such, though that has value. It was about letting a person and a less-than-positive culture reduce my standards for my own professional behavior. My integrity is mine to guard, and I let myself down that time.
All experiences shape you.
By contrast, when I left Radian6 this last winter, I took away an incredibly positive impression of my colleagues and the company, and the hope that we’ll all do lots more business together in the future.
Part of that was the organization itself, and the fact that the leadership worked very hard to create a positive environment overall. A big part of it was that the company had invested in me early and gave me a lot of freedom to grow. In the years that I was there, I had a lot of diverse experiences with different areas of the business, huge challenges, and great triumphs. All of those things helped shape the professional that I am several years later, and made me want to work really hard at making my transition out a positive thing for everyone.
My business partner Matt Ridings and I talk often about the idea that everything you go through is part of what makes you who you are. The ugly stuff, the amazing stuff, all of it. Looking back on a fifteen year career, I can honestly say that moments that I absolutely did not understand at the time (and that I was convinced were destined to send me to the loony bin) were as much a part of who I am today as the successes, perhaps more so.
If you’re stuck in a particularly challenging phase of your career, there’s still a lot you can learn, even if it’s about what you don’t want to do or become in the future.
Courage is defined by being afraid, and doing it anyway.
When I meet people in person that I’ve talked to online, there is one consistent thing they mention to me. It’s usually something about how ferocious/strong/fearless I seem. Or how I’m tough enough to chew iron and spit nails. Which always makes me smile, because I am truly anything but.
In fact, if I’m honest, I’m terrified a lot of the time. My ass-kicking persona is partly who I really wish I was, and partly a whole lot of defensive stuff designed to keep the world at arm’s length. Frankly, that backfires more often than not, intimidating people from getting near me, much to my detriment at times. We could do a whole psychoanalysis session on just that part of things, but here’s the point. There is no one on the planet who quits their job, starts a business, and never has a moment of trepidation or full on gut-level fear. If they say they don’t, they’re lying to you.
The trick is this. If you want the change bad enough, if you want to do something for yourself and branch out in a new direction, you can’t wait until the opportunity is perfect. It’s like having a kid. It’s NEVER the right time. You’ll always be in the middle of projects or up for a promotion or wonder if you can earn the same salary. You’ll always wonder if the opportunity you have is the better than the one you’re trying to create. You’ll always fear making the wrong choice or failing. My first business did well, but I decided to take an opportunity with Radian6 that put me back in someone else’s employ but gave me lots of interesting challenges. I had a successful career there that I could have continued at Salesforce.com after the acquisition, and instead I’m betting the farm on the unknown of a brand new business. It’s off to a promising start, but it’s far from guaranteed.
The ones who eventually succeed aren’t the ones who mitigate risks all the time. They’re the ones who take them, over and over and over again with the fear in the pit of their stomach, until one pays off.
Have a money plan.
The biggest mistake that I made in my first business venture was not having enough money in the bank. Remember, I quit angry, which meant I quit without having a fully formed plan in place and the support structure to make it happen. I had about three months’ income set aside, and that was it.
That money was quickly absorbed with regular costs of living in those first few months, which meant that the business was largely bankrolled on personal credit (which subsequently took me quite a while to pay off). I got lucky, and I secured early and regular clients that paid on time and caught me back up within a couple of months, but that was a risky proposition. And it’s not a mistake I would repeat.
Having a money plan doesn’t have to mean that you have tons of cash to burn or funding up to here. What it does mean is just that; understanding the realistic uptake of your business and how long it’s going to take for it to start earning revenue. In that timeframe you’ll need money for your personal expenses as well as the startup costs of your business, which can be minimal or significant depending on what you’re endeavoring to do, but they’re rarely nothing. Crunch some numbers, and if at all possible, spend the time to sock the money away before you ditch the day job. It’s not easy, but it’s the smart way to roll and it means you can stress less about making ends meet and focus on building your business.
Your time has value, even when you’re new.
Be careful about the temptation of doing a ton of work for free or giving away a bunch of free stuff to “get your name out there”. It immediately devalues you and your time, which is the last thing you want when you’re starting a new business.
Creative compensation can be one approach; doing things in trade for other services/products, joint marketing initiatives with trusted partners, working with a non-profit as a pro bono account. There is a keen balance between creating awareness and diluting the value of what you’re offering. I can’t give you a precise formula, but if you feel desperate, you probably look desperate. And if you don’t do the money planning thing above, that pull can grow exponentially when you think you’ll do just about anything to earn a buck for the business.
If you think the business was valuable enough to solve a problem or fill a market need at the start, you need to hold fast to that value and think long and hard before you give it up. It’s really difficult to get back once you do.
I could probably keep writing this post for days, outlining all the things I’ve felt and learned and regretted and loved and been proud of in the adventures between working for someone else and working for myself. But I want to hear your lessons, because there are lots of you out there who have gone out on your own, and lots of questions from those of you that WANT to but haven’t yet (I know because you come and talk to me at events all the time).
Write a post, and post a link here, or share your experiences, questions, and learnings in the comments. It’s the age of the entrepreneur, and there are many adventures to be had.