Being an entrepreneur is like being transgender.

No, seriously. Trust me. I know what I’m talking about here. (:

First, you need to think really hard about what you want.

Becoming a new gender? Becoming a new business owner? First you’d better be sure that you’re following your heart. Search deep inside to make sure you’re doing it for the right reasons.

Once you know what you want, you’ll do whatever it takes to achieve it.

There are lots of obstacles to both entrepreneurs and transgender people, especially low-income transgender people. But when you know what you want and are passionate about achieving it, you’ll do your best to overcome each and every one of those obstacles.

You’ll need to become good at learning new things.

Estradiol. Progesterone. How your body will change. The thrice-bedamned Harry Benjamin Standards of Care. How to find a good therapist. Surgery. How to come out to friends and family. How to come out at work. How to come out to someone you’re interested in dating (or are already dating). Clothes. Makeup. You can talk in the restroom now! Eye contact. Speech patterns. How to change your voice. How to change your body language. Sex. Orgasm. Social gender roles. How to be a lesbian. How to date women as a woman. How to be bisexual. How to date men as a woman.

Accounting. Distribution. Fulfillment. Marketing. Permission marketing. Tax law. How to incorporate. Social networking. Blogging. Podcasting. Vidcasting. Skype. Pricing. SEO. Web design. WordPress plugins. Marketing copy. How to tell people about awesome stuff without being annoying. How to make friends with awesome people without being annoying. How to ask for help. Self-publishing. Business planning. E-commerce. Credit card machines. Referral/partner programs. How to find a good venue.

You will recreate yourself, and it will be painful.

When I transitioned from male to female, I created a new social persona for myself, one that better fit my internal self-concept. My friends and family had gotten used to interacting with Boy Pace for 20-odd years. When I became Girl Pace, I changed in many ways, although in many ways I stayed the same. Everyone’s social expectations were flummoxed because I no longer fit into the same social role. It was uncomfortable and awkward, both for me and for everyone else. I would sometimes spend less time with my friends who had a hard time adjusting, to avoid having my feelings hurt due to male pronouns, social awkwardness, and feeling misunderstood. This shift was difficult and painful. I spent more time with some of my new friends who hadn’t met me before I transitioned, because I didn’t have to deal with their old, stale expectations. Also I hung out with several other trans people because we were interested in talking about similar things.

Becoming an entrepreneur was surprisingly similar. I created a new social persona for myself, one that better fit my internal self-concept. In this case, my self-concept shifted from “a smart, creative computer geek” to “a passionate, effective lightworker who turns her dreams into reality.” My friends and business associates had gotten used to interacting with Geek Pace for almost 30 years. When I became Lightworker Pace, I changed in many ways, although in many ways I stayed the same. Everyone’s expectations were flummoxed because I no longer fit into the same role. It was uncomfortable and awkward. I would sometimes spend less time with my friends who had a hard time adjusting, to avoid becoming demotivated or depressed by negativity, because we shared fewer common interests, and because I felt misunderstood. This shift was difficult and painful. I spent more time with some of my new friends who hadn’t met me when I was Geek Pace, because I had more in common with them and we were interested in talking about similar things. More of my new friends were also entrepreneurs and lightworkers, whereas my old friends were living lives more like Geek Pace’s life that I had joyously left behind.

You will face your fears.

What if I turn out to be an ugly girl? What if my family disowns me? What if I don’t have what it takes to make this happen? What if I can’t do it because I don’t have enough money? What if I go broke? What if all my friends hate me? What if I lose my job? What if I lose the respect of my friends and peers? What if someone uses male pronouns for me in front of everyone? What if they laugh at me? What if I look ridiculous? What if they see through me and realize that I’m terrified? What if I lose my true self in a jumble of newly practiced body language and speech patterns? What if my voice is too deep? What if no one will want to date me? What if no one will accept me as I am? What if no one will love me?

What if no one wants to buy what we’re selling? What if no one finds our services valuable? What if no one cares? What if I don’t have what it takes to make this happen? What if I go broke? What if I get a lot of flak and negative comments? What if someone criticizes me in front of everyone? What if they laugh at me? What if they see through me and realize that I’m terrified? What if I lose my true self in a jumble of dollar signs and business plans? What if I lose my friends because I accidentally turn them into networking acquaintances? What if I burn out due to overwork? What if I fail because I don’t work hard enough? What if no one likes what I have to offer? What if no one likes me?

You will fail without self-knowledge and inner strength.

These fears will eat you alive if you let them. The only way to succeed is to truly know yourself — to grow into a person who is knowledgeable and self-confident enough to be able to handle those fears. Let your fears inform you, thank your fears for guiding you to a touchy spot, and then dig in. Figure out what the root cause of your fear is, and then use that as fertilizer for personal growth. Grow bigger than your fears.

Entrepreneurship and gender transition are crash courses in fear-facing. Your issues will come up. Your landmines will be stepped on. Your triggers will be triggered. Each of these disasters is an opportunity for growth. If you can maintain a positive attitude even through the toughest challenges, if each time you fall down you learn a little more about how to get back up, then your self-work will eventually manifest in outward success.

I wish you the best on your path of becoming.