The Secret True Life of an Entrepreneur
Many people wonder what it’s like to be an entrepreneur. I am often told “You’re so lucky to run your own business! You work from home, do cool work, don’t have a boss, and get to be like a titan of industry or something.”
Yes – I do love being an entrepreneur but a few things need to be clarified about the lifestyle. If you want to know what it’s really like to be an entrepreneur, grab your coffee and settle in – I’m about to take you behind the secret curtain. Warning: it’s *not* like being the guy in the picture about to board the plane.
First – I’m not “lucky” to be an entrepreneur. I bust my ass every day to do it. I’ve earned being an entrepreneur and all the benefits that go along with it. Luck is where preparation meets opportunity and being an entrepreneur requires tons of preparation.
Second – I do have a boss. Two, actually. Their names are Wells Fargo Home Mortgage and the United States Treasury. They take pretty much half of everything I make. Unlike most bosses in corporate America, they’re not very forgiving when I miss budget…
Now, as far as the average day in the life of an entrepreneur, it’s not always as glamorous as it’s made out to be in all these tech blogs, magazines, and books. And working from home isn’t the highly productive and totally chillaxed lifestyle most people believe it to be. To debunk some of these common myths and misconceptions, here’s a look at an average day for me. It’s an aggregation of many real events:
5:25AM – wake up.
5:27 – day-old coffee heated up. Time to rock.
5:28 – read the news including critical blogs like FailBlog.org, FreakJet.com, and textsfromlastnight.com. Get suckered into watching a Yahoo “news” video that is falsely labeled as a news exclusive but it’s actually some lame attempt at comedy.
6:03 – personal hygiene. You gotta look pretty if you want to be a titan of industry! (Some mornings this part takes longer if I’ve ignored shaving for several days or if I need a longer shower to wake me up).
6:23 – email catch-up. Delete all Viagra, Nigerian inheritance, Canadian pharmacy, penny stock gazillionaire, and parental spam emails. Respond to the one “real” email in the pile with “Okay. I can push our coffee back to 9:30.”
7:16 – hear a strange hacking sound behind me.
7:17 – clean up Gunner’s dog vomit (Gunner is my Jack Russell Terrier. Elapsed time: 10 minutes. It was a lot of vomit).
7:27 – begin working on an urgent client proposal that the client wants immediately.
7:38 – stop working on urgent proposal because kids next door are waiting for the bus and while they do, they bounce 647 basketballs simultaneously while screaming at the top of their lungs.
8:27 – almost done with urgent client proposal
8:28 – Angel (my boxer) whines at me. I ignore her and keep working on the urgent proposal.
8:34 – notice an odd smell. Angel stops whining.
8:35 – clean up Angel’s poop that she cleverly dropped on the other side of my desk (out of my line of sight) while I was ignoring her.
9:07 – finish urgent client proposal. Send to client. Receive out of office response that they won’t be back for two weeks. Urgent, huh?
9:17 – send email to a client’s Accounts Payable department about an invoice that is 4.5 months overdue. “Oh. Sorry. We can’t find it. Just resubmit it and we’ll pay it on the standard net 60 days from the date we receive it.”
9:28 – arrive for networking coffee with another local entrepreneur. He’s not there yet.
9:38 – he’s still not there.
9:40 – I leave. He never called or texted. It’s always fun getting stood up.
9:47 – Local entrepreneur calls. “Hey, I’m running a little late…” Reschedule the meeting.
10:15 – back at the desk. Prepare for big, important one hour long client conference call at 10:30.
10:54 – deep into the client conference call. All is going great. Looks like I may make a sale.
10:55 – FedEx guy rings the bell (despite the big “Please don’t ring the bell” sign I post over the doorbell for when I’m on conference calls). Buddy (my poodle-schnauzer) goes ballistic like the four horsemen of the apocalypse are at the door. Gunner and Angel join in the barking for good measure. I frantically search for the mute button on my phone. Accidentally hit the power button instead and disconnect from the client.
10:59 – put dogs in their kennels. Call client back and sheepishly resume call. Call resolution is “we really like the proposal Mike. Let’s connect in a couple of months and discuss getting our VP involved to evaluate the proposal.”
11:28 – lunch! Go raid the kitchen with hopes of a banquet. Warm up leftover Manwich and baked beans. Go to the pantry for some Doritos goodness. All that’s left are crumbs but someone put the bag back in the pantry anyway.
12:02 – do some strategic thinking about my business. Big long-term thoughts kinda stuff. To get in the proper mindset, look at my awesome aquarium because it’s soothing and serene. Begin thinking big ideas.
12:04 – notice the angelfish I paid $95 for is dead at the bottom of the tank. Commence dead fish recovery and removal operations.
12:18 – admin hour. Pay taxes. Pay bills. Send invoices. Forecast cash flow. File bank statements. Rewrite three contracts. Set up four conference calls. Book travel including air, car, and hotel for five different trips (which part of me dreads because I’ll likely be traveling alongside some of these folks). Delete more Nigerian emails (if those guys ever get a hold of someone who is fluent in English, they’re going to bring down the world economy).
1:19 – new high score on Minesweeper.
1:22 – update company website and moderate blog comments. Update twitter feed, Facebook page, write new blog posts for the coming weeks. Try to decide whether to write something new and original or to recycle an old post.
1:34 – As I’m deciding whether to write something new or recycle that old post, the yard maintenance guys arrive and begin mowing and blowing the yard with their 900000000 HP jet engine packs. Recycling the old post it is…
2:00 – Coaching conference call with a team of five clients.
2:07 – While discussing the intricacies of problem solving methods, I hear a rustling behind me. Turn around to see Gunner has folded his pillow in half and is getting amorous with it… vigorously amorous. Suppress a guffaw while coaching clients. Unfold Gunner’s pillow and tell him to settle down.
2:08 – Gunner folds his pillow in half again and resumes his activities. Gives me his “do you mind? A little privacy, please.” look. I debate between stopping him or putting on some Isaac Hayes. I choose the former.
2:23 – nap. (Seriously – this is honestly the best part of being a work-from-home entrepreneur).
2:27 – kids next door get home. Resume their basketball game from the morning. Awesome. It’s only murder if they catch you, right?
2:40 – follow up on the sales pipeline. Drop emails and calls to 27 separate prospects. 5 have left their roles to join new companies. 6 are out of office for anywhere from 3 days to a 6 month sabbatical. 2 bounce back as undeliverable. 13 calls go straight to voicemail. One call gets answered. The reply is “we’re doing a reorg so give us a call back in 6 months.”
3:16 – son is home from school. Violates the “doors closed means don’t interrupt me” rule. Asks if he can buy something on iTunes.
3:18 – son comes in again. Asks if I finished the Doritos.
3:19 – son comes in again. Tells me Gunner puked in his kennel.
3:21 – commence vomit cleaning operations.
3:29 – son comes in again. Learns what a death glare is. Son doesn’t reappear for the rest of the day.
3:42 – calculate last month’s revenue generated from various advertising programs on multiple web properties I own. Sources include Amazon Affiliate, AdWords, TextLinkAds, 888Media, Adify, and PulsePoint. Grand total is $126.29. Awesome. Update cash flow forecasts accordingly.
4:16 – calendar planning. Schedule 6 coffee meetings, 3 lunches, 5 conference calls, 1 rescheduled coffee, and 3 training sessions. Sync to BlackBerry. Sync software deletes 42 appointments. Reschedule 42 appointments.
5:19 – quitting time. Go pull weeds, clean dog poop, change outdoor lights, and other homeownerly type things.
See? It’s totally glamorous being an entrepreneur. I get tons of work done in the solitude of my home office and I work on things that make me a true titan of industry. I hope some of you are inspired to pursue the entrepreneurial lifestyle after seeing what it’s really like.
Note: I *do* love what I do and I wouldn’t trade it for the world. My clients are fantastic, the work is fun, the flexibility is great, and the people are interesting. I’ve shared plenty of other thoughts on entrepreneurship here on the blog. I encourage you to read those as well if you are currently an entrepreneur or are considering becoming one.

















Mike,
LOVE IT! It is so so true, I’ve shared with my team and now I am inspired to go out and lead my team! lol The life of an entrepreneur is never the same from day to day, maybe that is why we LOVE it so much!
In the early 90’s, I tried the entrepreneur life leading an upstart Web site, before stressing out to the point that I decided to sell the site to a Chicago publishing company for a reasonable net gain. I work for a corporation now for many years as an individual contributor making as much as a CEO of a small company. Yes, the freedom of running your own company was great fun but also very stressful and the hours were almost unbearable. Yes, working from home is much better than working in an office tower but being home all of the time can be stressful too. Knowing the two sides, I’ll pick the lower stress 9-5 job over worrying about how I’m going to raise capital or how to increase my income as my expenses rise. So here I am for some remaining years in the corporate life before retirement, giving up past roles as entrepreneur and a writer for a magazine without regrets.