Career Advice
I Started My Own Company: Ten Lessons I Learned
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No one was more surprised than I was when I decided to launch my own company this past July. I had left my stable marketing gig at Google, and was all set to apply to new startup jobs in San Francisco. As I started thinking about applying to other jobs though, what I quickly realized was that I didn’t want any of them! I wanted to be my own boss and create my own freedom. But what kind of company would I start?
In order to clear my head and figure out what I wanted to do next, I started going on urban hikes throughout the city. Urban hikes weren’t new to me, but being between jobs gave me the time to explore all the far-off places I hadn’t had a chance to visit before: the 16th and Moraga mosaic steps, Andy Goldsworthy’s art in the Presidio, Fort Funston, etc. I would stare in wonder at the amazing hidden sights San Francisco had to offer, and then it hit me” other folks might want to see these spots too. Thus was born Urban Hiker SF, my urban hiking tour company!
The past three months have been a time of great personal and professional growth, and I’ve already learned so much. In case your cubicle days are also numbered, here are ten lessons I learned in the first three months since I started my own company that may help you too:
1. Starting a business can put you on an emotional roller coaster
Since I’ve started my business, one minute I feel I’m going to burst with pride, and the next minute I feel earth shattering pangs of anxiety and doubt. When you don’t have the security of a full-time desk job at someone else’s company, there are many more ups and downs to your daily life. As I go through each day, I’m learning to feel both the positivity and negativity without letting one or the other dominate my overall future outlook.
2. People will question what you’re doing (i.e. haters gonna hate)
Around San Francisco, it seems like everyone is doing a tech startup of some sort. No matter how good (or bad!) the idea is, people understand the idea of a tech startup and assume you’re up to something interesting. However, when you tell them you’re founding a non-tech startup, they don’t know how to categorize you, and they sometimes look at you with profound confusion. Whenever you do something outside the norm, the fact is that people are going to judge you. My advice is to ignore those folks and keep going on your merry way.
3. People will come out of nowhere to support you
In addition to the haters, you’ll also find that sometimes people come out of the woodwork to help you. People admire when you put yourself out there and do something unique. Within two months of launching my urban hiking business, I found myself in talks with companies like Match.com, Canogle, and SFBay.CA. These companies noticed my business because it was different, and approached me for partnerships
4. You gotta hustle
In order to get yourself out there, you have to do a little self-promotion. You’re not bragging” you’re marketing yourself! Make sure all your friends and contacts know what you’re doing, and reach out to potential partners proactively. There is no shame in putting yourself out there. In fact, that’s the only way to gain visibility and awareness!
5. You don’t need seed funding or a million dollars to get started
The week after I decided to start my company, I was going to a conference in Portland, and figured this would be a great way to get the word out about my business. With $30, I printed some business cards, bought a domain name, and created a website. Yes that’s right, $30 and I had a business. It was truly that simple. Two great books on creating your own scrappy startup are Chris Guillebeau’s $100 Startup and Less Work, More Money by Levo’s own Maxie McCoy.
6. You need to think about how you will finance yourself/company
For the past five years, every two weeks, my bank account would seemingly magically fill up with funds. Now that I don’t have a steady paycheck, sometimes it feels like my savings are burning like wildfire. I’m very happy I was diligent about accumulating savings all these years because I’m depending on some of that money now to start my business. Be realistic about your lifestyle and how much you spend, because budgeting is more important now than it ever has been.
7. Say yes until you can afford to say no
When I launched Urban Hiker SF, I had a list of things that I thought were below me. I didn’t want to do hikes for a single person, for example, because $45 for 3 hours just wasn’t worth my time. I then realized that I couldn’t afford to say no to offers just yet. Each hiker – even a solo hiker – could be a new connection, a new TripAdvisor review, a referral for future hikers, etc. When the money is readily flowing, then I will start saying no, but for now, it’s ”yes’ all the way down.
8. You need to be disciplined
I used to hate micromanagers, but now I’ve learned I need to micromanage myself. When all your time is your own, you need to be disciplined in how you use it. Can you do a Mad Men marathon in the middle of the day? Yes. But should you? Heck no! Each week, I plan out my week on broad strokes and then plan my days out the night before. This keeps me accountable and helps me stay on track.
9. You are going get up close and personal with uncertainty
Being an entrepreneur is definitely not the safe road. Your business could fail, and nothing is certain. But…that’s also the fun and adventure of it. As long as you’re out there hustling and trying your hardest, your business will stand its best chance of success.
10. You’re going to learn a lot” now get out there and launch!
No matter what type of business you launch, you are going to learn a lot. You’ll push yourself out of your comfort zone, and you’ll also make mistakes that you won’t want to repeat. Whether it’s a partnership, a marketing campaign, or a new logo design, you’ll test things out and see what works. Then you’ll move on to other challenges…maybe like creating your next startup.
Photos Courtesy of Get In Travel and A White Carousel.




well-writtenuseful advice,laced with encouragement
Thank you for this article. I like it a lot.