Twelve Lessons Learned from Twelve Months of Being An Entrepreneur.

In November of 2015, I walked out of my office for the last time and set out on a precarious journey of building a new vision of life that I could call my own.

I did not know exactly how I was going to do it, but I knew I needed to start.

The security of corporate employment, real or imagined, was no longer enough for me to justify staying in a career that was not right for me. After getting an MBA and working several years in corporate brand management, I had reached the point of burn-out. Last year, I finally took the jump and transitioned to a more balanced life while pursuing my lifelong dream of becoming a storyteller.

To describe what it is that I do now, I’ve created a term: wanderpreneur.

I am an incessant wanderer. I have been to ten countries this year and will visit three more by year’s end.

I am an entrepreneur. I make a living from telling stories about the world and from any other opportunities that come my way or, more frequently, that I have created.

I work for myself, which means setting my own hours, building my own plans, incentives and motivations, and relying on no one else for every single dollar that comes into my bank account. It has been the scariest step I’ve ever had to take (and I’ve taken many), but it has also been the most rewarding.

Over the last twelve months, I have had many false starts and dead ends. I have also made a lot of progress and learned a few things along the way.

Here are the essential twelve:

1. Get used to people telling you ‘no’.

We often don’t act on our plans simply because we are afraid to hear ‘no’ in response.

Get desensitized to that word. A good way to practice hearing ‘no’ is to approach strangers and ask them for things. I’ve asked a barista for a free cup of coffee and a man on a street for $5. I’ve offered to give a hug to one complete stranger and gave another a compliment. Most of the time, people will look at you in a funny way and say ‘no’. Sometimes, they’ll stop and talk to you about what you’re doing. Occasionally, this small conversation may lead to an unexpected good outcome. And the whole time you’re learning that getting a ‘no’ is not the end of the world.

2. Don’t give up.

Most people give up too soon. Building your own vision, just like any ambitious project, is a marathon, not a sprint. The acclaimed Eat, Pray, Love author Liz Gilbert faced thousands of rejections before her first story was published. ”The Accountant” star Anna Kendricks could barely afford rent while she was on a PR tour for ‘Up in the Air’. If you are serious about going after whatever it is that brings you joy, be prepared to stay in the race.

3. You’ll likely need to wear many hats to make it work.

Breaking in as a newcomer in any industry without prior experience or connections is not easy, and paying travel journalism jobs are far and few in between as it is. I’ve realized that in order to stay the course, I need to diversify my income streams. For me, that means starting marketing consulting projects, social media gigs, even walking dogs on weekends (whatever it takes!) as I nurture my new career.

Figure out what skills you have to offer — we all have some.

Better yet, ask your friends what skills you have. Your friends may be better than you are at recognizing your strengths.

4. You will need more time and more money than what you’ve originally planned for.

When I started on this path, I gave myself six months to “make it” before I even knew what “making it” looked like. There were two things wrong with that goal: too nebulous of an objective, too short of a timeframe. I’ve since readjusted and reworked my goals, recognizing that it takes time to build something great.

5. Whatever you want to be, call yourself it before you are it.

Start believing in your vision before others do.

About six months into my journey, I’ve hit a virtual wall. I’ve just come back from a round-the-world trip only to find out that back home, life went on. My friends got engaged and promoted in their corporate jobs, and I felt lost and had no idea what my next step should be. That is when I jotted down 10 things I will become in December 2016 on a physical piece of paper and put it up on my wall. Without realizing it, I’ve created a map for my vision that I could now execute against. Most things on that list have already become a reality!

6. Don’t take ‘no’ for an answer and institute a practice of relentless follow up.

Learn the difference between a ‘no’ that means ‘I’m busy, and I don’t know you, so I won’t take the effort’ and a ‘no’ that means ‘I am not interested in what you have to offer’.

The former is an invitation for you to do a better job at selling your idea, while the latter is a firm ‘no’. However, if you do your homework, the likelihood that a person you’ve engaged with is not interested in what you have to offer will be low. When I pitch ideas, I often receive a ‘no’ (after ton of following up), but it is almost always the first type of rejection.

The old me would stop right there.

The new me, the wanderpreneur, responds with more details and examples of the idea and often gets the ‘yes’.

7. Try as many things as you can between now and next Friday.

You have to put yourself out there.

Sometimes, being your own boss man or woman is a numbers game. Find events, conferences, meet-ups, and people with similar interests. When you bring forth enough of projects into the world, some of them are bound to bear fruits. Those fruits may not be the ones you’ve expected or wanted, but they will be the fruits of your labor nonetheless.

8. What you’re going for may not start making you a living for a long time.

Be ready for it. Have a back-up plan. Be prepared to pivot as much as needed to stay in the game. Realize that you’re in it for the long haul.

9. Fear does not go away, but it becomes easier to be afraid and still act on things that scare you as time goes by.

Just like you exercise your body on a regular basis, you’ll want to learn to exercise your ‘acting in spite of fear’ muscle. It becomes easier with practice, because our minds have this incredible ability to learn. When you take that speech gig and do it in spite of your fear of public speaking, your brain will record a ‘See? Nothing bad happened!’ memory. Next time, you will be a little more likely to take on a new thing that scares you.

10. Embrace failure.

What would you do if you knew you could not fail?

What would you do if you knew you would fail for sure? Would you still proceed? Because fail you will. Often. Many paths you’ll take won’t lead anywhere. Until one day, completely unexpected, some of them will suddenly open up to a field full of accomplished dreams and, better yet, new possibilities.

11. You are not alone.

Find other people who are trying to do something different. There are many.

The importance of having a community of people that have similar struggles and aspirations cannot be overstated.

When I left the corporate world, I felt incredibly alone and misunderstood, for who in their right mind leaves the security of that behind, especially in our uncertain times? Turns out, many people want to transition into a more meaningful work field, and I’ve found a group that works for me. Find yours.

12. This will likely be the most difficult journey you’ve ever taken.

There will be doubt. There will be fear. There will be stress. There will be judgement. There will be estrangement of friends and worry of family.

But this road will also bring you a lot of joy, because this will truly be the road you have built yourself, brick by brick, mistake by mistake, success by hard-earned success.

Perhaps for the first time, you’lI stop feeling that you are living someone else’s life and will instead have a strong conviction that you are headed in the right direction.

And that is something worth taking a risk for.


Originally published at on December 2, 2016.

Originally published at