We’re 5! Five lessons from the last 5 years.

It’s hard to believe that today marks 5 years since I embarked on my “2nd career” as an entrepreneur. On January 3rd, 2012, I turned in my badge and laptop, performed a perfunctory exit interview, and walked out the doors of my 9-5 Fortune 500 marketing gig for the very last time. That afternoon, I met a friend (who had also quit her job that day) in downtown Santa Monica for a celebratory lunch. (It was burgers and champagne, and they tasted like freedom.)

I’ve learned a lot in the last 5 years, and I’m sure there are an infinite number of lessons yet to be learned.

Since it’s my 5th birthday, here are 5 lessons I’ve learned (so far):

1) There’s never a perfect time to start, so start NOW. A year or so into my solopreneur life, I had lunch with an old colleague. He said, “I’m so jealous of you. You seem so happy, you’re doing what you love. I wish I could do that.” I asked, “What’s stopping you?” What followed was a laundry list of excuses:

• I need to save more money before I leap.
• What if I fail?
• I don’t have a great business idea.
• I need to write a business plan.

On and on… and while some of these are perfectly justifiable reasons, it doesn’t mean that you can’t start right where you are. Small. Start a side gig. Don’t worry about failing – in fact, celebrate and learn from them. Brainstorm for ideas – every day, make a list of 5 “problems” that need solving, or 3 things you’re good at, and see if those aren’t a good jumping off point for some kind of business. And, take a page from my friends at the Kaidan Project – and just do it. They made an entire show happen in just 2.5 weeks.

There’s no need to get precious about the details. Decide you want to start, and then do it. There will never be a perfect time, because the perfect time is NOW.

2) Life is a cash flow game. (If you don’t do the work, you don’t get a paycheck. That’s it.) When you work a salaried job, the paychecks show up every 2 weeks regardless of whether you’re working or on vacation. You kind of take for granted the money will be there. But when you work for yourself (and this is especially true for those who are truly solo – no spouse or significant other to help with the income), you realize very quickly that you must manage cash flow.

You’re in charge of business development. You’re the head of sales. It’s up to you to go out and get the work. And if you’re not getting the work, you’re delivering the work or following up on the work you delivered. Because that’s how you secure follow up work.

Even with a savings cushion, this was a scary feeling for me. I’ve been an “adult” for a while now, but now I truly understood why “adulting” is hard. There were months where I’d audition but book nothing, and then have a run of bookings for both VO and consulting work and be exhausted but happy for the paycheck. Feast or famine.

And now, having experienced the financial roller coaster (and the emotional roller coaster that comes with it), I’m learning how important it is to look at yourself as a portfolio business. As in: when you work a 9-5, typically that is 100% of where you earn your money. As an entrepreneur, my income comes from coaching, consulting, voiceover, acting on camera, and occasionally, through miscellaneous side projects. When acting gets slow, it helps to know that I can focus on consulting work to help smooth the cash flow… and vice versa. (And now you know why your actor/musician friends have “survival jobs.”)

3) Prioritize your exercise and relationships – you can’t stay in the bat cave 24/7. When you work an office gig, you have to be social, whether you want to or not. You are surrounded by people. When you work for yourself, sometimes it’s easy to get isolated. I joke that I spend most of my day (especially while auditioning) talking to a wall. (And because my VO booth is a closet, I’ve dubbed it the “bat cave.”)

After a few hours, I need to get out, take a walk and get some sunshine and fresh air. What I learned is that I needed to be more proactive about my social life – setting up exercise dates (even if it’s a solo run), coffees and lunches, or having plans in the evenings. Otherwise, it’s too easy to just work 24/7.

Having that social life keeps me sane and healthy – I’m able to catch up with friends, get some exercise, bounce ideas off other smart people, and just breathe. And then I can return to my desk (and recording booth) feeling refreshed and ready to tackle the next project.

4) Find a community that will help support and encourage you. If it’s true that you are the sum of the 5 people closest to you, then make sure they are people who will nurture, encourage, support and challenge you (in all the right ways). I’ve had to make some tough calls because my life choices weren’t what others wanted for me.(You can hear a bit about this in a conversation I had with Entrepreneur on Fire’s John Lee Dumas.) The world is a lonely place if you think you have to go it alone. (BTW – you don’t.) Your tribe is there – it could be your family and friends, it could be people you’ve connected with via social media or in past (or current) jobs. When we choose the entrepreneur’s path, we just have to get a bit more creative about where we look for our community.

5) Find a system that works for you. I’m fortunate that I’ve always been something of a productivity nerd. I read David Allan’s  “Getting things Done” when it first came out – and then spent a weekend implementing GTD on my work and home life. I’m looking for ways to smooth out processes and make life easier. I track my workouts, my auditions, my business development (client wish list). And I treat my days like work days – scheduling the important work, scheduling thinking/project time, and even scheduling social time. Having a system helps me to feel like my days are productive and focused, and keeps me from spending the days in my pajamas binge-watching shows on Netflix and calling it “research.” I find it ironic that while I’ve found myself rebelling against certain parts of corporate structure, I also crave structure in my working life. I think what it boils down to is that I love the autonomy of having my own business,  but I need to have routines in place so that I can get things done.

BONUS Lesson #6) Pause for gratitude.  It’s so easy to get bogged down in daily living. Especially when you’re working for yourself. Some days are a breeze, some are a struggle. Now more than ever, I’m aware at how fortunate we are that we live in a day and age where technology allows me to work from home, if that’s what I choose. It wasn’t too long ago when you had to go to work, because that’s where the resources (adding machines, typewriters, computers) were, and because your bosses demanded face time, whether you got any work done or not. This is where the gratitude comes in. I’m so lucky and grateful that I get to do work that I love, with people who inspire me, on my own terms. And I’m grateful I get to share this journey with you.

Thanks for sticking with me for these past 5 years (and some of you – even longer than that)! What can I do to help make your journey a little easier? Let me know in the comments.