Reality Check Ins For Entrepreneurs

There is little more liberating than being able to call all the shots in your professional life. Running your own ship, making your own calls and curating your own calendar are just some of the glowing benefits of being a freelancer or entrepreneur. But with no one to hold you accountable when your productivity seems to wane, it can be a slippery slop to the shores of ‘slacking off’. And we’ve all been there…

Me: We need to schedule in that client meeting ASAP. Does tomorrow morning work?
Also me: Ummm…
Me: Say, 9AM?
Also me: I meeean…
Me: Just get it out of the way, first thing?
Also me: Yeaaaah, but…
Me: C’mon we really need this project!
Also me: But…the tennis is on so…
Me: Fine, I’ll schedule for midday.
Also me: Thanks boss.

If no other separate physical entity is telling us what to do and when to do it (and that’s the way we like it) then how can we check in with ourselves so that we don’t fall completely off the work wagon? The answer is: be your own boss. Boss yourself around a little. In my experience (and perhaps in yours too) bosses have commonly sent things like requests, warnings, suggestions and feedback in the form of emails. So why not throw on a different pair of glasses, pull your pants up a smidge higher and get a little creative…

Here are a few emails I have written, to myself, playing the role of a far more domineering superior than I actually am.

SUBJECT: Phone usage at work

Dear Paige,

Hope your morning is off to a constructive start.

Let’s jump in: yesterday I noticed you spent a considerable chunk of the day scrolling on your phone. While I understand that Instagram is a valuable resource for networking and research, 5.75 hours a day (yes, we timed you) is probably overkill and likely not a profitable use of your time.

As each employee of this company (i.e. you) is required to have a mobile service I will not be confiscating anything from you on this occasion. I do, however, advise you ponder these simple suggestions for spending time less needlessly on your device during work hours:

1. Do not use your phone while eating – it’s messy and bad for digestion
2. Do not take your phone to the toilet – it’s awkward and others might be waiting
3. Limit yourself to checking your socials three times a day for a maximum of 10 minutes per check until work hours are complete
4. Unfollow all food, bikini model, vegan cosmetic and drone photo accounts – we are aware these are your kryptonite

I look forward to your improved mental health and KPI’s next month.

Your boss,


SUBJECT: Lapse in administrative tasks

Dear Paige,

A quick note to remind you the end of financial year is fast approaching and I’ve noticed you still have a shoebox full off receipts and an empty ‘TAX’ excel spread sheet in on your desktop.

While it’s all well and good to persist that you’ll “catch up tomorrow” or “next week” or “before you die”, records prove that in fact you avoid “catching up” at all costs. When running your own enterprise, sadly, this option is not available.

An option you do have, however, is to make the painstaking process of organising invoices and noting expenses a little less, well, painful. Here are some tips I have seen work for our other employees in the past:

1. Make a ritual out of it by taking yourself to a nice lunch once a fortnight. Crunch your numbers over your lettuce and commit to having all your tedious admin finished before you ask for the bill. PS. Add that bill to your expenses too – technically it’s a business meeting
2. If your admin is taking up too much of the day, weigh up your own hourly wage against that of a bookkeeper’s. Consider employing someone else to help you parcel your papers so that you can spend your own time more wisely
3. Go back to working for someone else

I hope this advice fills you with the gusto you need to cross all your t’s and dot all your i’s. I will endeavour to check back in same time next year.

Kind regards,


SUBJECT: Attitude check in

Dear Paige,

It has been brought to my attention that over the past few weeks you have been displaying somewhat of an unjust sense of entitlement. Although I appreciate that your skills are refined and you have “an impressive portfolio of past clients”, I would like to remind you – gently – that there is nothing overly unique about what you do. That is to say, in offering a bespoke creative service. Don’t get your cables in a cluster; you as a person are one-of-a-kind, yes! Your chosen profession, however, is not.

The work will not always fall into your lap just because you hang out at the right beach clubs, wear the right type of hats or have one of those wooden Macbook laptop covers. Let us not forget that as much as you believe your clients need you, you also need them.

The intention of this email is not to reprimand but rather inspire you into a more industrious and entrepreneurial mindset. If you deserve nothing more than you give, then what more can you contribute to attract the right opportunities into your orbit?

Speak of which, here is a simple exercise in “giving” I would like you to complete before the end of the day:

1. Send five emails offering free consults
2. That’s all

Ouch, your ego, right? No pain, no gain. Approach these consults from a place of adding value. Maybe none of them will convert, maybe one of them will, but at the very least you’ve done something good. Remember how that feels again.

I look forward to watching the fruits of both your professional and spiritual labour bloom.

Your boss,


SUBJECT: Go for a damn walk

Dear Paige,
You’ve been sitting at the same desk, with the same crooked posture for 12 hours now. That’s the equivalent of the whole first season of West World (including recaps), three fifteen-minute power naps, a French manicure and a slow cooked chicken. When was the last time you got up to pee?

I’d like you to go for a walk, smell some fresh air, take a break and drink some water.

In fact, you’ve probably worked hard enough for today. Sign off.

You boss,


Holding oneself accountable doesn’t need to be daunting. By committing to “check yourself” every once in a while, you are opening up the doors to a realm of limitless growth and opportunity. Sounds cheesy but it’s true. You’ll sooner make a million dollars working for yourself than you will for anyone else, but just remember whom that responsibility to make the first million belongs with.

On entrepreneurship, Steve Jobs says: “Those who are crazy enough to think they can change the world usually do.”

If that means sending emails to oneself in third person, then call me crazy


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