This month marks 4 years since I start­ed Hot Pep­per Com­mu­ni­ca­tions, and ear­li­er this spring, I passed the 2-year mark since I start­ed doing it full-time.

Even though I’ve been in busi­ness for myself full-time for only 2 years, I’ve been run­ning busi­ness­es off and on for near­ly 20 years. Here are 17 lessons about entre­pre­neur­ship I’ve learned dur­ing that time (some of them more recent­ly than oth­ers):

1. I must have a flexible schedule.

I tell peo­ple that I don’t work 9 – 5, I work 5 – 9. I’m often work­ing until 21:45 and at it the next morn­ing before 5:00. That can be tax­ing, but I also have flex­i­bil­i­ty. I can take off an hour to go to a non-prof­it board meet­ing or two hours to go with my fam­i­ly to an agri­cul­ture fair.

2. I must be comfortable with inconsistency

Every work­day is dif­fer­ent. While I do the same type of work each day (writ­ing, edit­ing, and social media), it’s always some­thing new. Run­ning a Twit­ter account for a real­tor, for exam­ple, is not the same thing as run­ning a Pin­ter­est board for a fur­ni­ture man­u­fac­tur­er. Edit­ing a master’s the­sis is not the same as edit­ing a mag­a­zine arti­cle.

3. It’s easy to get a raise.

With my employ­ers, I had to wait for a raise or accept annu­al cost-of-liv­ing increas­es. Now, if I want a high­er income, I just need to sign on new clients. It’s all up to me.

4. I’m around my family more.

Even though I work in a des­ig­nat­ed office space, I can still hear my fam­i­ly inter­act­ing. When I stop for din­ner or to get a drink, I can inter­act with them. I can hear them laugh­ing and chat­ting about ran­dom things. I love my fam­i­ly, and being around them more (even if I’m kind of not) is a great bless­ing.

5. I can nap.

Because of my long work­days, I am often tired. If my day isn’t too hec­tic, I can find a few min­utes to relax, put in some earplugs, cov­er my eyes, and snooze. If I don’t do this, I often drift off. A quick nap reju­ve­nates me and helps me car­ry on. I can’t do it every day, but when I can, it makes a huge dif­fer­ence.

6. I must be super motivated.

It was easy to get into a rut when I worked for some­one else. Now, I’m always moti­vat­ed to find more clients and increase my brand aware­ness. It was always some­one else’s respon­si­bil­i­ty to do those things, now it’s mine. Lit­er­al­ly, if I don’t do it, no one else will.

7. I must work long hours.

As I said above, I work 5 – 9. That’s actu­al­ly pret­ty typ­i­cal. I have plans to hire employ­ees in the near future, but before I can do that, I need enough work for them to do. Until I do that, I have to do all of the work.

8. I get no holidays.

In the last 27 months, I have tak­en 3 week­days off: Christ­mas, my uncle’s funer­al, and the day after surgery. For Christ­mas, I moved all of my work to the fol­low­ing Sat­ur­day. For my uncle’s funer­al, I spread my work through­out the oth­er days; in fact, it took me three days to recov­er from the back­log. For my recov­ery day, I sim­ply charged my clients less.

Because I am my only employ­ee, if I don’t work, the work doesn’t get done. If I took hol­i­days, I either charge my clients for work I didn’t do, or I give them a reduced rate and take home less. So, no hol­i­days.

9. Saturday is my Friday.

I take Sun­days off. It’s the only day I take off. As a result, Sat­ur­day is to me what Fri­day is to every­one else. I have a 6-day work week.

10. My pay is intermittent.

Some clients take months to pay me. Some clients have me do small job which are only, say, $10 or $20 worth. It’s dif­fi­cult to bud­get when you have no idea how much mon­ey you’ll make, espe­cial­ly in the ini­tial stages of the busi­ness. Things are start­ing to sta­bi­lize, so it’s less of an issue than it used to be. Even so, clients come and go, so the mon­ey com­ing nev­er stays the same for long.

11. People forget I’m working

Every so often, I will get a phone call from some­one ask­ing me to help them with some­thing dur­ing the day. Some­times I can help, but usu­al­ly I can’t. They always seem to phone when I’m try­ing to meet a dead­line, too.

12. Some clients take months to pay you.

If you’re going to start a busi­ness — espe­cial­ly a B2B busi­ness — don’t depend on all clients pay­ing you imme­di­ate­ly. Some of my clients have tak­en months to pay me. I’ve only ever had 2 delin­quent accounts (and they were each only $40), but some do take a while to pay me. Be pre­pared to either live on very lit­tle some months or make sure you have reserves set aside.

13. Some clients take months to sign up.

While some com­pa­nies are quick to sign on as clients as soon as I meet with them, oth­ers take their time. Nev­er depend on poten­tial clients as a source of income until you’ve actu­al­ly done work for them and billed them.

14. Some clients require reminders.

Peo­ple are busy, and this is quite appar­ent when your busi­ness pro­vides ser­vices (rather than prod­ucts) for oth­er busi­ness­es. Whether is get­ting approval on a final draft, get­ting a pay­ment on an invoice, or ask­ing for feed­back on anoth­er project, some of your time will be spent try­ing to track down clients. If you don’t have patience, you may not be cut out to be a busi­ness own­er.

15. It’s hard work getting clients.

Send­ing out a mass email to all your con­tacts will pro­vide rel­a­tive­ly lit­tle busi­ness. Buy­ing adver­tis­ing space for B2B ser­vices will pro­vide rel­a­tive­ly lit­tle busi­ness. Don’t expect all your adver­tis­ing efforts and mon­ey to result in new busi­ness. Some of it will see like a waste. If you aren’t good at sales, you’re going to have quite a go of mak­ing your busi­ness work.

16. Be prepared to fail.

Per­son­al­ly, my wife and I have failed at run­ning a busi­ness 8 times. Hot Pep­per Com­mu­ni­ca­tions is our 9th busi­ness, and final­ly, it’s been our most suc­cess­ful. It‘s kind of fun­ny actu­al­ly because 9 is my favourite num­ber.


Fail­ure is part of entre­pre­neur­ship. It’s one of the risks you must be will­ing to take if you ven­ture out on your own. In my opin­ion, it’s a risk worth tak­ing. You will learn more lessons through fail­ure than you will in a text­book. You will learn that forces exist that are out of con­trol and that will tear you down. You will learn that you need to be able to live off noth­ing some­times if you want the busi­ness to sur­vive. You will learn that you can’t live your life as if your client is going to pay their invoice this month.

17. It’s tough being an introvert.

I’m an intro­vert, and I have anx­i­ety. That makes it dif­fi­cult to cold call and to reach out to new peo­ple at net­work­ing events. Busi­ness grows more slow­ly for intro­verts, but being suc­cess­ful is pos­si­ble.

Do you run your own busi­ness? What are some valu­able lessons you’ve learned?

About Kim Siever

I am a copy­writer and copy­ed­i­tor. I blog on writ­ing and social media tips most­ly, but I some­times throw in my thoughts about run­ning a small busi­ness. Fol­low me on Twit­ter at @hotpepper.

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