11 Lessons from a Year of Full-Time Entrepreneurship

Now that I’ve been running my own business for a year, an awesome reader requested a lessons-learned post.

So here are 11 lessons I picked up during my first year of work freedom:

1. Who you work with has a huge effect on your happiness. And one of the best parts of working for yourself is you can choose who to work with (and who not to work with). I used to feel guilty about passing on projects simply because the person I’d have to work with stressed me out, but then I realized: the whole point of working for myself is to NOT be stressed out.

Find ways to work with great people, and pass on everything else. You’ll be so much happier that way.

2. Saying no is more important than saying yes. The smartest entrepreneurs and writers know they can’t execute all their ideas. Because we have SO many ideas, right? That’s why we’re good at what we do!

But what separates the good from the great is being able to capture those ideas without acting on every one. Instead, choose the ideas (and clients and projects) that will most help you get where you want to be, and focus there. If you try to execute everything, you’ll end up doing nothing well.

3. Sometimes you have to focus on what pays. Sure, you’re in a lifestyle business to do work you enjoy, but you still have to pay the bills. You’ll never find work freedom if you don’t make enough money to support your lifestyle. So when you’re bombarded with requests to write guest posts (for free), ask yourself whether that work will truly pay dividends. Sometimes the payment will be in web traffic or personal connections, but other times you’ll need to bring in actual bucks.

Don’t feel guilty about this. To succeed as a business and create the life you want, you have to make money.

4. Going after clients isn’t always the best way to land new business. Here’s what has worked better in my world: helping clients find me.

How do you do that? The easiest way is via an online presence. This post explains more.

5. If you want time off, you have to make it a priority. No one will make time off for you. This applies to most traditional jobs, but even more so to entrepreneurship. If I want a weekend to relax or hang out with family, I have to block off those days as non-work time — and stick to it.

And guess what? If you don’t answer emails for a weekend or avoid non-emergency correspondence after 7 p.m., the world will not end. Your business will still thrive — perhaps more so, because having time off will help you enjoy work more when you do sit down at your computer.

6. Most of us feel fulfilled when we’re learning and growing. Years ago, I thought I’d be a journalist forever. And I still am, in a way — that experience and knowledge will forever affect how I communicate. But surprisingly, I can be happy doing something other than journalism! I feel a tad bit of nostalgia when I’m at parties with my journo friends who’re talking about riding in the presidential motorcade. But I’m so excited about the projects that I’m working on — and so enjoying learning along the way — that I don’t miss what I thought was my professional life calling. I feel totally fulfilled, satisfied and happy with my work.

And so I ask you: if you’re NOT feeling happy and fulfilled with your work, how can you introduce more learning into your life?

7. Outsourcing isn’t just for Tim Ferris. Hiring a team (of 6-7 contract workers, not employees) is the best thing I’ve done for my business. Several readers have asked how I got started with this, so watch here for a post soon with details.

8. Sometimes you have to spend money to make money. Newbie entrepreneurs tend to be wary of this adage — either that, or they go overboard, putting way too much money into their business upfront. You really don’t need a huge investment to start your own side hustle or full-time business, but sometimes it’s worth spending some money.

For example: I quickly learned my guides would sell faster if I outfitted them with a professional cover, since that’s potential buyers’ first impression of the product. I pay $150-300 for an ebook cover, and usually earn that investment back quickly. Go ahead and be lean, but not too lean.

9. An email list is invaluable. This is something I wish I’d known when I first started my biz as a side hustle years ago. Blog subscribers are great, but email subscribers are better. (Click to tweet this advice.) Why? Because you can go to them rather than waiting for them to come to you.

Now that I put effort into a newsletter, my list is growing fast, which results in more blog traffic and more purchases of my guides and courses. (Want to get my newsletter? Sign up here for helpful and inspiring letters that are different than what you read on the blog.) If you’re starting a blog or business, start collecting emails as soon as possible.

10. You have to earn more money while working for yourself than you do as an employee. Kind of insane, but true.

This can feel like a hard hit each quarter when you pay estimated tax payments. But just remember to take that into consideration when you figure out how much you need to make to reach your desired standard of living and how much you need to charge to get there.

11. Creating and selling info products is a genius way to make a living. Not only is it FUN, but you can create your product once and sell it many times over — it’s a much better return than, say, writing a freelance piece for a magazine. Plus, you have complete autonomy when it comes to creating and promoting the product.

This is another huge ah-ha I wish I’d stumbled upon years ago. Now that I get it, I’m runnin’ with it!

Your turn: If you do any kind of freelancing, consulting or entrepreneur-ing, what’s the biggest lesson you’ve learned so far?

Like this post? Check out Turn Your Side Hustle Into a Full-Time Business & Surpass Your Day Job Income in Just 6 Months.