1. What’s your favorite hobby?
● Sometimes a hobby can turn
into a side business, as it did for
skydiver Sydney Owen. While
working at a public relations
agency, she took up skydiving
on the weekends, and then
started handling marketing for
the skydiving company. Now,
she runs her own marketing
business on the side.

2. What do you already do for free?
● Are you the person everyone
asks for computer help? Or
graphic design insight, or social
media tips? If so, that expertise
can turn into a coaching
business or consultancy. That’s
what happened for Douglas Lee
Miller, a social media expert
who now consults on the side.

3. What’s your most marketable
skill?
● If you’ve worked in an in-
demand field, from website
design to public relations, your
expertise can probably be
parlayed into a side business.
Public relations consultant
Megan Moynihan found that
after leaving her agency, she
could pick up her own clients
and work for herself.

4. What kind of legacy do you want
to leave?
● Sometimes the lessons or stories
you want to pass on to your
children can turn into products that
others are interested in as well.
Prakash Dheeriya initially wrote
personal finance books for his own
sons, but soon realized that other
parents wanted to teach their
children similar lessons. The
finance professor has now
published a 20-book series aimed
at young people.

5. Are you part of a community?
● If the community you wish
existed hasn’t yet taken form,
you might be able to build a
business out of creating it.
That’s what Emily Miethner,
founder of NY Creative Interns,
discovered after launching a
series of events designed to
connect entry-level
professionals with more
experienced creative-types.

6. How can your friends help you?
● Many new entrepreneurs find
that friends are essential to
getting the word out about their
new businesses, especially at
the beginning. Jewelry designer
Erica Sara had her friends host
trunk shows for her wares and
made connections with potential
customers through her running
blog.

7. Does your full-time job easily
convert into freelance work?
● If you work in a specialized
field, such as information
technology, public relations, or
design, you might find that your
skills are also in demand on the
freelance circuit. Websites such
as freelancer.com, elance.com,
and odesk.com make it easy to
post your skills and search for
freelance jobs.

8. What do you need help with?
● If you have a weakness—perhaps
you don’t know how to use Twitter,
or you stumble over proper
grammar—you might want to enlist
the support of an online course,
ebook, or coach to help you
through those rough spots. After
taking an online course on making
money, twenty-something James
Mundia was able to build his
soccer training business.

9. What do you read about for
pleasure?
● As with weekend hobbies, your
reading habits can also provide
insight into how you’d like to
spend your time, and how you
might be able to make money. If
you love reading about new
media, perhaps a Twitter
coaching business is for you. Or
if you enjoy perusing Pinterest
or Etsy, perhaps some type of
crafting career is in your future.

10. Can you find a role model?
● In almost every field, no matter
how niche, there is usually
someone already doing
something similar to what you
want to be doing. That person
can help you, especially if they
blog, Tweet, or write about their
process. Seeking out these
types of mentors, even if you
don’t interact with them directly,
can help you build your own
business.