Greatra Mayana

Career & Employment Opportunities

The Thrills (and Chills) of Self-Employment

It’s now my pleasure to
introduce our speaker for the day, College of
Communication alumna Jeanne Yocum. Jeanne has been self-employed
as a public relations consultant and ghost writer for
more than 30 years helping large corporations,
small businesses, nonprofits, and self-employed consultants
promote their business. This past spring, her new book,
The Self-employment Survival Guide, Proven Strategies to
Succeed as Your Own Boss, was published by
Roman and Littlefield. Her blog,, has offered advice to
small business owners and solopreneurs since 2010. A Pennsylvania
native, Jeanne holds a BA in journalism
from Penn State, and a master’s
degree in journalism from BU College
of Communication. After spending most of her
career in greater Boston and Western
Massachusetts, she now lives in Durham, North Carolina. Jeanne, thanks so much
for being here today. I know you’ve just returned from
a tour promoting your new book, so congratulations on that. And we appreciate that
you’re taking time to be with us in
the BU community. I’m going to go ahead and
turn the floor over to you. So if you want to go ahead
and get your slide deck up and running, the
floor is all yours. OK, thank you very much, Jeff. And thank you to
BU for providing me with this opportunity
today to talk about one of my most favorite topics,
which is self-employment. And welcome to all
of those of you who have logged on to learn
more about this topic. I want to say right up front
that I never for one second regretted my decision in
1989 to become self-employed and to become my own boss. And as a result,
I’ve always been eager to share the
lessons I’ve learned, both through my own experience,
and through watching the many, many clients
I’ve had over the years who have been self-employed. So we’re off. I wanted to spend just
a few minutes talking about what’s happening in
self-employment in America right now. 16.7 million Americans
were self-employed in 2017. That’s a little over 10%
of the American workforce, and doesn’t include tens
of thousands of people who moonlight, or
what everybody now is calling having a side hustle,
in addition to their full time job. Since 2014, self-employment
has grown three times faster than the workforce as a whole. In other words, for every
person who enters the workforce, three people become
self-employed. Other trends. There’s a prediction– at
first, you look at this and you say, well,
how can that be? But I’ve seen this from
several different sources that by 2027, 50%
of the workforce will be self-employed. Now that’s for two big
factors rolling into that. First, it takes into
account the ever-growing use of independent contractors
by businesses of all sizes. Those people are counted
among the self-employed. Secondly, many of the people
folded into that forecast will be self-employed
only part time, and they will be
having one of them side hustles that I mentioned
earlier while they hold down a full time job. Some of those will be hoping
that that part time thing will grow into a full
time gig so they can be fully self-employed,
but some of them will be happy to keep it
just as a side hustle. Self-employment–
sorry about that. I’m skipping a slide here. self-employment plays a
big role in the US economy. Three out of every 10 jobs are
held by self-employed people and the workers they hire. That’s a huge
impact and something I often think could use
more focus by state and city governments, which tend to
spend their resources chasing after the big employers,
and more or less ignoring small employers and
the self-employed. I know here in the Durham
area, the Research Triangle, we’re chasing Amazon and Apple
for big new campuses here. But I wonder how much
attention is really paid to the part of the segment
that generates three out of every 10 jobs. So who is it? Who are these
self-employed people? This is the last
part of the section that I want to talk about. It may seem counter intuitive,
but one of the fastest growing segments of the self-employed
are retired baby boomers. There are three
reasons behind this. First, some baby boomers
retired, and then realized that their financial
resources were not going to be adequate to support
the lifestyle they wanted in retirement. So they’ve taken
on a side hustle to supplement their income. Secondly, a lot of people– and I know some of these
people personally– have decided to take
up an income generating activity that they always
wanted to do, but never could because of the pressures
of their careers. In many cases, this is
some form of creative work, like being an artist of
some type, being a writer, making videos. Some people have gone
to work part time for nonprofits whose mission
they believe strongly in and that type of thing. Again, most of them aren’t
doing this full time, but they are generating income. And I hope fulfilling
a lifelong desire to express themselves through
a creative activity that has always interested them. Finally, some boomers are
finding retirement boring. This is my generation, so
I can speak with authority when I say that we’re
used to being very active, and sitting at home doing
nothing is probably not going to work for most of us. So perhaps we start a
part time consulting gig in the field in which
we spent our careers. Or again, we may take up some
creative income producing activity that is totally
unrelated to what we did in our careers. Like I say, I belong to
the Osher Lifelong Learning Institute at Duke
University here in Durham, and I’ve talked to dozens
of members who have taken up some kind of income
producing activity once they left
corporate America, or perhaps the small
business they left behind. Or in many cases, they
had their own businesses, which they sold and now
are doing something else. The other big population
segment of course involved in self-employment
is the millennials. And nearly 50% of
them are already freelancing either full time,
and in many cases, part time. Back when I entered
the workforce, it was common for people to
spend their entire careers working for one company. That notion is dead
now, and people are used to moving from job to
job throughout the continuum of their careers. As a result, I
think we can expect more and more millennials and
members of the generations coming after them to
give self-employment a try at some point along
that career continuum. Maybe the right job
just isn’t coming along, so they think when
they are moving on from their last company. And so they think, let
me give self-employment a try for a little while and
see if that will work for me. Now, today’s topic. So that’s what’s
happening in regard to self-employment in America. And if you’re considering
joining in on this trend by becoming your
own boss, I want to help you further understand
what being self-employed is actually like by talking
about these three topics. First, the benefits
of self-employment. And I know that I’m going to
talk about some things that you probably hadn’t thought
about if you’re not already self-employed. As you know, my presentation is
called the Thrills and Chills of Self-employment, and when
I talk about the benefits, that the thrills part, the
part that makes it worthwhile to be your own boss. Then I’m going to talk about a
few myths of self-employment. These are things that
most people believe are true about being your
own boss that often are not accurate, or not completely
true for everyone, or they’re just
vastly exaggerated. Here’s where some of
the chills in the title of my presentations comes in. I’m going to try to
bring a dose of reality to the preconceptions many
people have of self-employment. And finally, I’ll discuss
the self-employment mindset you need to succeed
over the long haul. There are both thrills and
chills in this section. Things that can be great when
you tackle self-employment– things can be great when
you tackle self-employment with the right mindset. But if you don’t, you may
encounter nothing but chills. But first, we want to
do a poll question. We want to find out
who in the audience– what your status is now with
regard to self-employment. So Jeff, can you
bring up the poll? OK, so are you
currently self-employed? Are you actively planning,
putting things in place so that you can be
self-employed in a year or two? Or are you among
the crowd who hopes at some point in the
your future down the line a little bit in your career
you could be self-employed? Jeanne, we’ve got about
half of people who voted. So we just give it just
a few more seconds. And while we wait for
those answers to come in, I neglected at my
introduction to mention folks, if you would please feel free
to use the Q&A function to ask Jeanne any questions that come
up throughout her presentation, you’re welcome to do so. And we’ll save time at the
end to cover those questions. If you hover over the bottom
or the top of your screen, you should see a little icon
for Q&A. Just click on that. We’ll also be using the chat
feature for another question later on, and we’ll cover
that when we get to it. But Jeanne, we have
a good majority of folks who have
voted in our poll. And I’m going to go ahead
and share the results. Are you seeing
those on the screen? I am. And I’m excited that 41%
are currently self-employed. I always like to
talk to those folks. And there is a
lot of information in my book for
example, that you’re going to run into
some stumbling blocks when you’re self-employed. And that was one
of my motivations for writing the book, to
help people figure out how to get around the
perils and so forth. 20% actively planning,
and 39% hope to be. So just the fact that
you’re tuning into a webinar when you see that some point
down in your future, I think is good. So I think those are great. Awesome. So I’m going to go ahead
and close this out. OK. So let’s look at the benefits
of being your own boss. Before I get into talking
about the benefits I found of being my
own boss, I want to just say a couple of things. That your list of benefits may
differ significantly from mine, and probably, it will. The rewards of self-employment
are different from each people– for each person, I believe. What makes you happy may not
be what thrills me day to day. And so I suggest that
you think carefully about what it is you’re
looking for in your work life, and build a business that will
match your particular goals and your particular
definition of happiness. I also want to point out that
when times are going tough when you’re
self-employed, it’s often good to have a list like this. As you’ll see when
I get there, I’m not talking about the
financial rewards, or the rewards of becoming
well-known in your field and so forth. Although for some people,
that is a big benefit that they’re going after. The kinds of things
I’m talking about are more about controlling
your own destiny and so forth. And if you have that list sort
of over to the side or maybe on your bulletin
board, if things aren’t going as
well as you’d like, it’s a good time to keep
reminding yourself of that, of what those benefits are. The more intangible
things that you’re getting out of self-employment. But if you’re off track and
not getting those benefits that you’re setting out to
get, looking at that list can spur you to perhaps
make necessary changes. So here are the six things
I write about in my book that I enjoyed most
about being my own boss over the past almost
30 years at this point. The first one is choosing which
clients I want to work with, and those to whom
I say no thanks. The last part of that
benefit, the ability to turn down business
from a prospective client, has always been
a biggie with me. And that’s because when
I started my business, I was coming from a
job with the PR agency where we had some great
clients, and we also had a few– I don’t know what to call
them other than duds. They were people
that I never would have chosen to work for if
the decision was up to me. I give an example in my
book of a real estate developer who said to me– and this is a verbatim quote– a monkey can write
a press release. And fortunately for
both of us, he said that during a phone call
and not in person, so I wasn’t able
to throw anything at his head, which was my
strong desire at the point. So I realized the
agency owner had to sign payroll checks
every two weeks. And obviously, that
weighed on her mind when she was going out and
bringing in new clients and bringing in new business. And we can all
sympathize with that. But once I was out
on my own, being able to turn down
potential clients who my intuition told
me would be a bad fit, or whose ethics appeared
to be possibly squishy, or for any other reason
that came across my mind was something that
I highly valued. I learned very early on–
and this is a lesson I would encourage each of you
to take to heart– to trust my intuition. Trust your intuition
about this kind of thing. And if something
is bothering you in that first meeting you have
with a prospective client, it’s probably going to
continue to bother you, and will bother
you more and more. Being the decision maker. I personally have
never had a problem making decisions and
sticking with them. In fact, I love being
the decision maker. But not everyone–
and I love not having someone make
decisions for me is one of my favorite parts
of being self-employed. I’ve learned over the years
however from my interactions with other
self-employed colleagues that being the decision maker is
not something everybody enjoys, or even anticipates will be
part of being self-employed. When you’re running
your own business, every single decision
is up to you. Obviously, you may have
mentors or colleagues that you can ask for
guidance and advice, but you make the
final decision about every single solitary thing. Only you can say for sure
whether you’ll regard this as a benefit or not. I personally loved it. But not everyone does. And I’m going to
talk more about this when I get to the
self-employment mindset part of my presentation. The ability to
control my own fate. This is perhaps what I’ve
found to be the biggest benefit of self-employment. I have numerous friends who have
been downsized more than once. And if any of you were
in the Boston area and were familiar with
Polaroid Corporation and what happened when
they went bankrupt, you’ll know what it
really means to be part of corporate America. Yes, their pensions
were guaranteed. But as a group, they
lost tens of millions of dollars they had invested
in the employee stock ownership plan. Polaroid was a client of
mine through the 1990s, so I knew a number
of people there, and my heart bled for them when
the company went up in smoke. Because of this and
similar problems I saw friends who worked
for someone else have over the years– including in the
great recession– I long ago stopped envying
these people their alleged job security. Knowing my fate was
mostly in my own hands and not in someone else’s
has been wonderful. Closely related to
this was the ability to control the direction
my business takes. When you’re an employee– and a
lot of people don’t think about this much– it’s your employer who decides
what type of work you do, and what skills
will get developed through training and
other opportunities that are put in your path. But when you’re
self-employed, you can take your career in any
direction that you want, just as long as you
can get somebody to pay you for that, of course. For example, after I
have been self-employed for about 10 years,
I felt the need for an intellectual challenge. So I decided that I was going to
add books to the list of things that I would ghost
write for people. And within two years, a book
I co-authored with a client was published. And having my name as a
co-author on that book gave me the credentials I
needed to start ghost writing books for others, which I
did over the next 15 years. That’s not the type of thing
you can decide when you’re working for somebody else. They are largely the ones
who control the direction your career takes. Your only choices when
you’re an employee and you want to
do something else is to perhaps take
on a side hustle to gain experience
in the area that you want to pursue, or perhaps
change your employer and go someplace else where they
might give you an opportunity to do that. Number five, the freedom to
work at home, set my own hours, and organize my life
the way I want it. Now here’s a benefit that
probably everybody who’s looking forward to
self-employment, they look forward to
enjoying this when they decide to be their own boss. I’m a night person by nature,
so having the choice not to get out of bed at the
crack of dawn, get gussied up and commute to work
suits me just fine. If I feel like
sleeping in, I do. Sure, I may work longer
in the afternoon, or maybe an hour on the
weekends to make up for that, but that works. For me, it’s worth it. And if I decide to
take a random day off, nobody is going to say,
no, you can’t do that. We need you here at the office. The same is true for
picking my vacation weeks. This control over my time also
means I can go to the gym, I can go do my grocery shopping
and so forth during the middle of the afternoon on the weekdays
when these places are much less busy than they are after
work and on the weekends. And I can take time off
during the day to volunteer. Or if the writing muse
isn’t just with me, I’ll go do whatever it
is that I want to do, and nobody’s going to– whatever it is that strikes my
fancy, I’m in control of that. Now when we get to the
myths section of my talk, I’m going to alert you to
the fact that you don’t– you can’t always
count on enjoying this benefit 100% of the time. More on that later. The final benefit that
I want to talk about is the ability to relocate. I’ve moved my business
twice in the past 16 years. I moved from eastern
Massachusetts to western
Massachusetts in 2002. And any of you who
live in Massachusetts will know that moving
beyond Route 495 is very similar to
moving to another state. I didn’t know a single
solitary soul out there. And when I contacted
my friends, it turns out they didn’t know
anybody out there either. So that turned out to be a
bigger move than I really thought it was going to be. But then in 2013, I
moved to North Carolina, where the cheaper cost
of living has enabled me to semi-retire at this point. And thanks to the
wonders of the internet, and because of the nature of
my personal business, neither of these moves mattered,
made any material difference in my career and my ability
to keep the business thriving. When I moved from
Boston to western Mass, I kept my Boston clients. Yes, they were only 90
minutes in on the pike, so that really wasn’t
much of a change. But when I moved
to North Carolina, I kept my Boston clients. I kept my Western
Massachusetts clients. I kept the client that
I’ve written three books with in Denmark. And I’ve kept a client in Texas,
and one out in California. So the internet is a
wonderful thing obviously, to people like me, and
to many other people who are self-employed. But you have that mobility
that you don’t have if you’re working for somebody else. So that’s my list of
what I’ve enjoyed most about being my own boss. If you’ve already embarked
on self-employment, I encourage you to put
together your own list. And if you’re thinking about
becoming your own boss, start thinking about what
your list might include. What are you looking for
in being your own boss? Myths of self employment. These are things that
people have constantly said to me over
the years, people who aren’t self-employed. When you meet them at
networking meetings and so forth, these
are the kinds of things they say to you. The first one, life
would be so much better if I didn’t have a boss. Well, I bet many of
you think that’s true. And in fact, it may be
your chief motivation for considering self-employment. Now, I’ve had some good bosses,
and I’ve had some bad bosses. And in the introduction
to my book, I write about the micromanaging
and other behavior of my boss that drove me to
quit my last 9:00 to 5:00 job. But until you’re out
there on your own, you may not fully consider what
it means not to have a boss. Here’s the reality. When you’re self-employed,
you don’t have just one boss, you have a lot of them, your
clients, or your customers, or whoever it is
that you’re providing products or services to. The main difference,
of course, is that you can always fire one of
these bosses if you choose to. That’s something I’ve seen a
lot of solopreneurs ignore. The fact that if a client
isn’t working for you, isn’t making you happy, isn’t
living up to their obligations, like paying you in
a timely fashion, you are not compelled to
keep working for them. You can fire them. I’ve fired many a client. And as I mentioned
before, I’ve also learned to avoid
taking on clients who my intuition told me were
not going to be my cup of tea. But the fact still remains that
when you are self-employed, you will have many, many people
making demands on your time, bringing stress of one type
or another into your life. And the fact is that the
more successful you are, the more clients you will have. And thus, the more demands
you’ll have to juggle. You will still have issues
with people who pressure you with deadlines, and people
who try to micromanage you, who shift directions
with little notice, or any of the other things
you might find irritating about your current boss. Yes, even clients can
try to micromanage you. I’ve had clients inquire about
the tiniest detail of something I was doing for them. And I have had
clients who wanted me to call them every single day
to give them a status update. All that did was
slow me down, it didn’t help the thing
progress any more than it would have without all this. None of it made sense. And if you happen to
have more than one of that type of client working
with you at any one time, it can be pretty miserable. So don’t think
ditching your boss will eliminate all
of your work woes. It won’t. Myth number two, I’ll get
control of my work/life balance once I’m self-employed. Another way people
express this is by saying I’ll have so much
freedom when I’m self-employed. Now, as I acknowledged
earlier when I was talking about
this as a benefit, this may in fact
be true at times. But almost certainly
it won’t be true when you’re just
starting out on your own. When you’re just starting
your own business, your work/life
balance may in fact be significantly worse
than it was in the job that you just walked out of. Your life maybe all
work and no play as you struggle to
build your business. There are very few
cases of instant success when it comes to
self-employment. Building a strong, long lasting
business may take a few years. So if you go into this thinking
that you will immediately be able to enjoy
a better work/life balance than you currently
do, you may be disappointed. And even once your
business is up and running and is really well
established, you’re going to have periods
when you’re working more than you would care to. For example, in the late
1980s, as I mentioned before, I decided I wanted to
ghost write business books. Well, the whole process
of persuading a client to work with me on that
book, of finding an agent, of writing the proposal, of
writing the sample chapters, of finding a publisher,
and then finally getting a contract, that took
about six or eight months. And while I was
doing that, I also had to do all of my other work. Because certainly until
we had a publisher and we were paid the first half
of our advance for that book, I didn’t earn anything on
the hours and hours and hours of extra time I was putting
in on nights and weekends working with my
client on that book. So I’ve seen many other
clients and colleagues who have done similar things,
taken on projects like that, crawled out of the limb to do
something that was not going to pay back immediately,
but would move their career in the direction,
their business in the direction they wanted to go. So the lesson here
is that you can’t afford to stay static
when you’re self-employed. And taking risks that may
or may not pay off often means working long
hours and forgetting about that vacation
you had in mind, and enjoying absolutely
no work balance at all– work/life balance at all. Now, did I have a wonderful
level of work/life balance thanks to being self-employed? Yes. Many times, I did. For many years,
particularly when I was living in
western Massachusetts, I took every Friday
off in the summer. So I would start
the summer knowing I had three months
ahead of me where I was going to work four day weeks. And that was fantastic. And I did take days
off and vacations when I wanted to take them,
rather than what an employer allowed me to take them. And yeah, you have more
control over your time. But that doesn’t
mean your life won’t be filled with client or
customer demands, which many times will conflict
with each other, and with your desire to spend
more time with your family and with your friends,
and devoting yourself to your non-work interests. Here’s a big myth. I’ll finally be doing
what I really love. Well, yes, you will. But a large part of
the time, you won’t. You should definitely choose
to do something that you love. You should definitely
choose something that you love to be at the core
of your self-employed life. For example, I love to
write, and have loved it since grade school. I was that person who always
aced the essay questions, and who had never seen anything
but an A in my report card in English. But writing is hardly
the only thing that I do. And whatever it is
that you love will not be the only thing you do. There’s this whole business
side of running a business that people forget
when they envision what their self-employment
is going to be like. There’s bookkeeping. There’s billing and collections. There’s learning new technology,
and coping with technology that has let you down. There’s keeping up your website. There’s doing social media. There is the whole
critical new business part where you go
out and convince people to become your clients. There’s writing proposals. There’s the networking, the
networking, the networking, and then some more networking. The list is endless. Now of course, you can
outsource some of this work, like the bookkeeping,
for example. But you may not be able
to afford that when you first start out. So please don’t envision
yourself sitting in your office, or your
studio, or your store that you’re
starting, or wherever it is that you’ll
be working and doing only what it is that you love
all day long and nothing else. If that’s all that you
do, you won’t succeed. In fact, I’d venture to say that
most of the people who struggle or fail at being their
own boss are those who ignore the
business side of things and never fully grasp how
critical these activities– unwelcome as they
may be at times– are to success. If you can’t adapt to the
need to network, for example, you are definitely going to
struggle to bring in the work that you love doing. It’s as simple as that. Here’s the final myth
that I want to talk about. If this self-employment
thing doesn’t work out, I can always go get a job. Well, that’s true in theory. But I think that it
gets to be more complex. Yes, you could just
polish up your resume and go back into the
job hunting world. But I think it’s much– it’ll end up being
much more difficult. First, I think there are some
prospective employers who will look askance at someone
whose resume has a recent stint in self-employment. They may question why you’re– whether you’re flying back to
self-employment because you failed miserably
self-employment, which might raise questions
in their mind about what your skill level– skill levels are and so forth. They may think you’re
looking for a short time to help you dig out
of a financial hole that you got into while
you were self-employed. And they may wonder
exactly what it was about you that caused you
to fail at self-employment. Secondly, and I think this
may be even a bigger issue, the psychology behind
going back to being an employee after being on
your own presents problems. Once you’re used to making all
the decisions for yourself, how are you going to adjust
to having a boss again? Will your failure to
succeed at self-employment be such a blow to
your self-esteem that you have a hard
time presenting yourself in a positive way,
and present yourself well in interviews or
other business situations? Will you always be looking
back over your shoulder and wondering why
you didn’t stick it out and try to make a go of
it out there on your own? I was first self-employed
from the spring of 1985, to the end of 1986, and then
went back to a 9:00 to 5:00 job. My biggest client kept
offering me a job, and I finally took it because I
had made the mistake of letting myself get burned out. Working 9:00 to 5:00
five days a week instead of working six
or seven days a week as I had been for quite a few
months looked very appealing. Well, once I took
the job, I found it impossible to go back to
being happy as an employee after being out on my own. I just missed steering
my own ship too much. I suspect many other people who
try this have the same problem. So please don’t think that
going back to being an employee will not present problems. Instead, it’s a better idea
to focus all your energies on trying to make a success
out of what it is you’re doing, so that you never
have to go back to working for somebody else. Now we have another
poll question that we want people answer
through the Q&A button, Jeff? Actually, we’re going to
use the chat for this one. The Q&A, Jeanne, only
allows for multiple choice. So folks, if you would
hover over your menu and zoom here either at the top
or the bottom of your screen and click on chat. You’ll want to go
ahead and answer this question, your biggest
worry about becoming self-employed. What do you fear most
about this challenge? And we’re going to
leave this up for– well, we’re going to have
the chat function open for a long time. But Jeanne, what
you wanted to do was actually cover
this sort of at the end of your presentation, right? Yeah. Before we go into
the Q&A, we can look at what’s bothering people
and see if I can help them with any of those things. So folks, I realize this
might be a little confusing, but if you’ve got
questions for Jeanne, use Q&A. And if you want to
reply to this poll question, your biggest worry about being
self-employed, use the chat. So Jeanne, carry on here. OK. So now let’s talk about the
self employment mindset. What are the essential
mental attributes that will help you succeed
at self-employment? I’m going to talk
about six things here that I’ve seen among my friends
and colleagues and clients who have been successful
at self-employment. These are things that
I feel they all have. These also in most
cases– the good news here is that in most cases, if you’re
not strong in these areas now, there are ways to develop them. And I talk about some
of those in my book. I will also say that some of the
people that I’ve learned from and figured out this
mindset from are in my book. I have seven
colleagues and clients that I bring into the
chapters and in sections called Other Voices. So they give their perspective
on the self-employment peril or issues I’m talking about
in any particular chapter. And I added it all up
one day, and it adds up to almost 200 years of
self-employment experience that these people and myself
all bring to the table. So I feel we know what
we’re talking about. So I feel fairly
certain that the things I’m talking about here in
the self-employment mindset are important to have. Persistence. Are you someone who is dogged? Are you someone who
is easily discouraged? When you’re self-employed,
you hear the words thanks, but we’re not
interested an awful lot. You must be willing
and capable of dealing with this kind of rejection. Persistence is
important not just when you’re seeking new business,
but at other times too. Say you’ve done
a job for someone and their billing’s overdue. You have to persist in reminding
them that they owe you money. As I write in the
chapter in my book that’s about dealing
with slow payers, the squeaky wheel does get paid. So don’t ever hesitate
to be the squeaky wheel. And if you are someone
who’s going to shy away from asking for the
money that you’ve earned, self-employment can be
mighty hard, and potentially, not very profitable. You might need to look into
assertiveness or communications training that will
help you become more comfortable at persisting
at being a squeaky wheel. Decisiveness. Until you step out
into self-employment, you may not have considered
that it’s probably the first time in
your entire career when you have the ultimate
power to make decisions. Previously, it’s likely
that someone else has always had decision making
authority over you. You had a boss who set
your priorities for you, and who ultimately had veto
power over your suggestions and ideas. Thus, you may have had
a little experience with making big decisions. Or in some kinds
of workplaces, you might not even
have any experience making little decisions, just
depending upon the type of work you’re doing. This all changes dramatically
when you become self-employed. As your own boss,
you are responsible for every single
choice that needs to be made about your business. You need to be able to make
decisions in a timely manner, and then stick with them. Indecisive,
wishy-washy people who constantly change
directions have a hard time with self-employment. Every day is filled with choices
about the direction you’re taking your business,
about what you need to do next to move
your business forward, and about the work you’re
doing for your clients. If upon reflection your
stomach gets a little queasy at the notion of having
to be the decider, then perhaps you should
consider delaying your dream of
self-employment until you become more comfortable
with decision-making. It’s quite possible that
once you get some more professional experience,
maybe even some more life experience under
your belt, you’ll become more at ease
with decision-making, and perhaps better prepared
for life without a boss. Risk tolerance. The list of
potential hazards you face when you’re self-employed
is long and daunting. Everyone who is self-employed
has cash flow worries from time to time. Everybody who is
self-employed has had to chase clients for
money that is overdue. We all worry about juggling
competing demands from clients in order to keep everyone
happy and satisfied. We all have clients– whoops. Didn’t mean to do that, sorry. We all have clients who
don’t meet their commitments, and cause the project you’re
working on to fall behind, making it necessary for us
to work nights and weekends to make up for their laxness. We are all at risk for losing
clients for external reasons that have nothing to do
with the quality of work or the quality of the
product that you delivered. And that doesn’t
even begin to address the larger set of
risks you undertake when you become your own boss. What if no one really wants
the service or product you’re providing? What if customers
or clients aren’t willing to pay enough for
your service or product to provide the level
of income you need? What if you quit your
job, and it turns out that you don’t really
like being self-employed? Yeah, that’s a list of
some mighty big risks. And you have to be risk tolerant
to live with that on a day to day basis. If you aren’t risk
tolerant, you may find yourself frozen in place,
unable to set priorities, make decisions, and take
necessary actions. Now, the good news is
that with experience, you will learn how to overcome
many of the risks you face. For example, as I
advise in my book, you’ll learn how to ask for
deposits before starting to work for new clients. So if they turn out
to be a slow payer, your cash flow won’t take
quite as much of a hit and be as much in jeopardy as
it could have been if you hadn’t gotten that deposit up front. And as you succeed in
facing and conquering more and more perils
that come your way, you’ll gain confidence in your
ability to stay the course and succeed. So risk tolerance is something
you can build over time. And that’s good news
for anybody who’s considering self-employment. Self-motivation. I heard this comment
hundreds of times when I’ve been at
networking meetings and told somebody I
was self-employed. They would say,
oh, good for you. I don’t think I have
enough self-motivation to be self-employed. I’m not sure I could stay
on track and keep focused. My response to that
has always been that what motivated me
each and every month was that the mortgage
bill arrived. And if that doesn’t motivate
you, I don’t know what will. But yes, it’s important to
really like what you’re doing. But most reasonably
well-adjusted people will find it within
themselves the motivation to do what needs to be done
in order to pay the bills. If you truly feel you
need external motivation, that you need a boss to hold you
accountable for getting things done, then self-employment
is not for you, I would definitely say. Confidence. There are a couple of
aspects to confidence that you need when
you’re self-employed. You need to be confident
in your ability to deliver what it is you
say you’re going to deliver to your customers and clients. You also need to be
confident in your ability to go out and meet new people
and persuade them that they should do business with you. This can be very
hard for some people. You may never have had to
get up in front of a room and present a business
idea about something that you’re proposing to do
for people for a company. You may never have had to
go to a networking meeting and introduce
yourself to strangers, and present your elevator
speech about your business. But you need to learn how to
do all those things confidently if you’re going to succeed. The best thing I personally ever
did for myself in this regard was to take a Dale Carnegie
course in public speaking. It was a big investment
for me at the time, but it paid off in so many
ways that I can’t even begin to tell you. Toastmasters is
another great program– and somewhat less expensive– that will help you
get comfortable so you can project the
confidence you need in order to succeed. These programs improve your
ability to project confidence, not just in front of a
group or a large audience, but also in one to
one meetings as well. The final thing I want
to talk about in terms of the self-employment
mindset is optimism. I won’t say definitively that
a pessimist can’t succeed at self-employment,
but I definitely think it’s easier
to succeed if you’re an optimist by your nature. People who are
attracted to people who have positive attitudes
and an optimistic outlook. It’s hard to convince
yourself to do business with someone who always
thinks the sky is falling. Also in my experience,
I found that pessimists spend far too much time
worrying about things that are never going to happen
to them and their business. And this is energy
they could use instead to be moving their
businesses forward. If you’re a pessimist, you
also have a harder time recovering from the
inevitable blows of fate that will come your way
when you’re self-employed. Each time you lose a customer
or a client for instance, you’ll take it harder than
someone who is a pessimist– who is an optimist, rather– and who works off the philosophy
that when one door closes, another one will open. Finally, before we
get to your questions, I want to quickly mention what
I view as the core elements that will contribute to your
success as your own boss. These are your core talents,
connections, and values. Your core talents are what
will determine your success as a solopreneur. Oddly, many people haven’t
even taken the time to analyze what their
core talents are. And as a result, aren’t prepared
to communicate their value to would-be clients
and customers. Of course, some of us know one
or more of our core talents from a very early age. I always excelled at those essay
tests, as I mentioned earlier. And I’m sure that I didn’t
have any teachers who were shocked by the fact that
I became a professional writer. If you think back,
I’m sure you’ll acknowledge that at least
one of your core talents was apparent very early on. What was it? And will you be
using that talent when you’re self-employed? Will it be like my writing– will it– like my writing–
be at the very heart of your business? If not, why not? Other core talents take
more time to emerge. I was over 40 before I
realized due to circumstances I had been through, that I
wasn’t just good at networking, I was darn good at it. This knowledge came
to me only after I had made several successive
moves to new areas where I didn’t know a
soul, but where I quickly managed to integrate myself
into the business community. This realization
is part of why I felt confident about moving
away from Massachusetts, where I had spent my entire work
life career, to come here to North Carolina. So what core talents
have you discovered as your career has progressed? And how will you be leveraging
those to move your new business forward? But if you haven’t
identified your core talents and aren’t focusing on them as
you choose the type of business you want to have, I don’t
believe you will actually be successful. I think we have to be
doing those things we’re really, really great at to
succeed at self-employment. So gain control
over your destiny. Assess your core talents
and make them work for you. The second part of
this success formula is your key connections. In every successful
self-employed persons life, there is someone who has
reached out a helping hand at a critical moment. This usually is someone
who has been unfailingly supportive, always willing
to listen when things are challenging,
and to cheer you on when things are going great. I call these people
your core connections. And they are the people who
have helped us achieve success. Your list will evolve over the
course of your self-employment. But it’s a good
idea to start now by identifying those people. On the other side
of this is you’ll also have to figure out
how you can support them in return, because it has to
be a two way street for this to really work. And the third and
final component here is your core values. These are the rules you’ll live
by in conducting your business. Sadly, many people
don’t take time to consider what values
they intend to operate their business under. This leaves them struggling for
an answer when they inevitably face business dilemmas that
require a values based choice. The core values I identified
for myself are simple. Key among them are
to be scrupulously honest in every aspect of
my dealing with clients, and to treat clients the
way I want to be treated. In my book, I write
about a few other values that have guided my work,
but those two values alone will get you a long
way toward success. As an example of putting
this into effect, I make it clear to
every new client that I will always give
them my honest opinion about their ideas
and their plans. I was never going
to agree with them just because I thought that’s
what they wanted to hear. I believe people are
paying me for my experience and my expertise, and
if they want a yes man, they should hire somebody else. So what are your core values? Having these things
clear in your mind will make it much easier to get
through the average business day, because the
right choice will become amazingly clear when you
work in a value centric way. Jeff, can we get the answers
now for the poll question about what is worrying people
about being self-employed? Yeah, Jeanne. We had some great participation
from our folks on the webinar today. I’m happy to read
them back to you, but do you want to
open the chat as well, or are you not able to see that
with the slide that you’ve got open? Oh, hold on a second. Hold on a second, let me– hold on. Oh, I see it. OK. Tons. I mean, Maria, making
income steadily instead of peaks and valleys. My biggest worry is
finding and paying for decent medical insurance. That’s come up a lot,
health insurance. Failure in health
insurance, staying busy, acquiring consistent
income and clients. The biggest challenge
is that it feels like swimming on an open ocean. How do I choose the right
priorities to focus on? That’s a good metaphor. It does feel like swimming on
an open ocean a lot of the time. Generating business, making
money to be self-sustaining. Yeah. A lot of these have
seemed to have to deal with income fluctuations. And I do write about
this in the book. There’s something
psychological that goes on when your income
is down a little bit. And this is particularly
a dangerous situation if you’re working in
a home office, which I did for my entire career. I dearly wish that some of
these co-working spaces that are popping up here and
there and everywhere now were available
when I started out, so I could have an
affordable situation that I could fit into,
and with all the benefits that those bring in
terms of meeting people who could help you and who
might be clients and so forth. But I worked at home. And one, because– I worked at home because that’s
what I could afford to do. And one of the things
that comes up for people is when things
aren’t going well, you have this horrible
tendency to want to stay away from that
office part of your house, because it’s negative in there. And that is exactly
what you strongly have to do with all your willpower. To get back in there,
and instead of saying, well, I’m not very
busy right now. This would be a great time to
paint the guest bedroom which I’ve been meaning to do. Do not let yourself
fall into that. You have to go back
in, get at your desk, put together a networking
calendar of where you’re going to go over the
next few weeks or months. Look at your marketing. What can you do better? Who can you reach out to? I talked about core connectors. Schedule a breakfast
with somebody who’s been a big support. Maybe they don’t
know somebody new that you could talk to
about potentially doing some work for, but maybe
they’ll just raise your spirits a little bit. Because it does come
and flow, ebb and flow. Obviously, when it’s rolling,
when the money is rolling in, put some aside for
the rainy day account. Now, I will be honest– as I am in the book– and tell you that I never
managed to put together a rainy day account. But I also am proud to
say that I always managed to pay my bills on time. So what would life have
been less stressful if I had managed to put
together a rainy day account? Of course it would. I did put aside
money for retirement so that I don’t have
any worries now. That’s another big thing
that you have to think about. And realize up front that you’re
going to be paying 15% out of every dollar for
your Social Security, because you’re paying that
whole freight on that. A lot of people don’t– that comes as a big
surprise to people, because they’re used to
having their employer pay half of that. You’re going to be
paying all of that. So those are some of
the things I can answer. The insurance
thing, god love you. I just– there’s no– I can’t really give
you any advice on that. Let me see some of these others. Re-entering the job market. I’m not sure if that means– I took that to mean
what you mentioned about starting
your own business, and then having to go
back, and maybe not finding the job market to be– Yeah. At some of those
book events that I had last week in Massachusetts,
the audience and I talked about that a lot. What I gather– I never tried to do that after
I did that one stint at the PR firm. Once I went out on my own
in 1989, I never even– it never crossed my mind again
to go back into the job market. But in talking to some
people, particularly at an event I had out
in Amherst, one or two people who had tried to do that,
I think part of it depends on– how welcome you’ll be depends on
what kind of field you were in. I talked to one woman
there who has actually done that several times. She’s going back and
forth from self-employment to back into the job
market, then hopped back in self-employment. And she’s back in
some employment now. It depends on what–
she’s in a field that is very highly desirable. She raises money for people. She’s a development officer. And those people, if
you have a track record, I don’t think it’s going to be
that hard for you to get a job. I think there are other
fields where people are more– the talent is more abundant and
more widespread over people. But I do think some
of those issues that I raised when I was talking
about that, of how people will look at that on your resume,
might not consider that a positive part of your career. I think it would pay you well
to think of questions that might come up around that
issue of why are you leaving self-employment, and have a
good explanation ready about why that didn’t work
out for you, or why are you want to go back
to being self-employed. Jeanne, we’ve got about
five minutes left here. I want to call attention. I think Grace made a good point
about some of her concerns around legal issues,
taxes, risk management. And that makes me
wonder, were there some sort of like small
business resources that you tapped into as
a small business owner during your career? Are there other sort of like
small business associations that people should look
into, that kind of thing? Yes. One of my favorite
clients of all time was a national
organization that works out of Springfield
called the National Association for Community
College Entrepreneurship. And that’s made up
of community colleges all across the country. And I got to know
those people very well. So many community colleges
have small business development centers. Many states have– I think possibly all states
have small business development centers the states run. You can go to these places. The ones that are at
community colleges, they offer very, very low
cost and sometimes even free workshops on very
important issues. Some of the basics, some
of the computer skills that you might not
have that you may need to pick up, like how to do
your bookkeeping and so forth, working with QuickBooks,
that kind of thing. Those are a great resource,
and a very, very affordable resource in most cases. Great. And then we’ve got one
question that’s come in. And folks, we’ve
got a few minutes left here if you want
to chime in with one last question for Jeanne. Chloe has asked something
that you’ve kind of– she asked it a few minutes
ago, and you kind of addressed at the
end of your talk. But I think it’s worth
sort of repeating here. So Chloe is a 2010 grad from
the College of Communication. She has hopped industries, and
when she quit her full time job, she fell into consulting
and self-employment with folks in her
network needing help on various projects. Chloe’s coined herself
as a jack of all trades for new businesses. But at what point does she
really need to specialize? Is she setting
herself up for failure by marketing herself
as a generalist? Without knowing what field
she’s in specifically, it’s a little hard
to judge that. Yeah. Coming into this–
I’ll just have to use my own field
as an example. Coming into this,
I was a generalist. And I was a generalist
for the first 10 years of my self-employed career. I did all kinds of
public relations. I did event management
and all of that type of thing, crisis management. Anybody needed their name
in the media, anybody who got their name in the
media for the wrong reasons who needed some crisis
management help, I did it. So that was being a generalist. Then I decided to focus
more on the ghostwriting part of my business, and– as I said several times– decided to write books. I think she has to judge that. If I were she, I would
talk to some of my mentors and get their advice on that. Because like I say, without
knowing the field specifically, I think being a specialist is
more important in some fields than it is in others. So I think that would be about
as much as I could answer. Jeff, I do want to
mention that if people want to go to my blog, and click on the big red
Learn More button there, they can download the first
chapter of my book for free. And that’s the chapter that’s
about being the decision maker and how that comes up for
people who haven’t really thought about that. They’re going to have to
decide every little aspect of their work lives
and their business and where they want to
take it and so forth. So that chapter’s
there for free. All the chapters have sections
called coping strategies to help you get better at
whatever it is the chapter is about, such as collecting
money from slow players and juggling competing
client demands, and going out and getting
new business and so forth. Great. Well, Jeanne, this
has been fantastic. And again, I do
encourage everybody to visit Jeanne’s blog. You’ve got your
email address here. So if you’ve got remaining
burning questions that you think you’re
willing to sort of field some final questions from folks. Always happy to hear
from my fellow alumni. Perfect. I have to do a small
plug as well, Jeanne. You mentioned several
times in your presentation the importance of
leaning on your network, having those core connections. And I want to make sure
that folks on the webinar know that BU is
a great community to try to build your network. You’ve all had that
shared experience of being a BU student
and now an alum. We have tons of resources
available to you as alumni that help
you build your network. This webinar is
being recorded and is going to be in our
library where you will find many previous
webinars about how to build your network
within BU and how to make strong connections with folks. And I encourage you to
check those out on our red– excuse me– on our
website at So Jeanne, on
behalf of everybody who’s here in the
webinar, thank you so much for this and for
doing this for our community. I enjoyed it. This was my first webinar
I’ve ever done, Jeff. You all treated me very well. Very gentle with me. So I may do another
one sometime. Well, you did a great job. So thank you again. I also want to thank
everybody for tuning in from all over the world. Specifically want to thank those
of you who’ve donated to BU. We have two great webinars
coming up next month in July. One’s going to be on integrating
video into your marketing. I know we had one
person mention marketing was a concern that they had, so
that will be a great session. And another webinar on
staying focused and increasing your productivity
in the workplace. For those of you
who have concerns about being your own boss,
that might be a great session to check out. Again, you can sign up for
those sessions on our website, And if any of you
would be interested, we’re constantly showcasing
some of our entrepreneur alumni. And if you, like
Jeanne, would be interested in doing a
webinar presentation for us, feel free to reach out to me
at the Alumni Relations Office, or by email at [email protected] So thanks, everybody. Thanks again, Jeanne. I hope you all have a
great day or great evening, wherever you might be.

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