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A Guide To Being Your Own Boss (And Loving It)

Think of the best and worst boss you’ve ever had.

What made them the best and the worst?

self-employment-be-own-boss-2345I’ll give an example (and I’d love to hear yours):  Fresh on a high school pizza place job, I became acutely aware that I was holding up the line.  All the pizzas were finished differently – some were topped with an oregano blend, others with special cheese, calzones were sliced twice and stuffed pizzas had a second layer of toppings.

I had to consult posted recipe cards to get each one right, while everyone around me whizzed through their tasks from memory.

The boss saw me get increasingly frustrated with myself, and took me aside, saying “You’re new at this.  Being slow is motivation to get better, that’s all.”

A few years later, new among the ranks of the self-employed, I was trying to get WordPress to do something and couldn’t.  It was slow.  Painfully so.  Frustrated, I started to tell myself “I am terrible at this.”

But then I thought – hold on now.

I don’t have a boss anymore.  I AM the boss.

Would I put up with a boss who said “You are terrible at this?”

How could I handle this instead?

This is a question for you, too.

Because YOU are also your own boss.  Yes, even if you don’t currently work for yourself.

You are in charge of yourself.  Your business.  Your creative work.  Your life.  No matter what.

These things happen under your management.

So let me ask you – have you given your boss a performance evaluation recently?  Looked at how you’re doing as your manager?

I’m guessing that some of you are working for bosses (cough cough) who you would never tolerate if they were a separable human being.

This isn’t some gimmick, either.  Self-employment or self-direction is really hard.  Manage yourself poorly, and your work and life will suffer.  Just like it would if you had any other terrible boss.  But do your job well, and you’ll inspire yourself with your progress.

So, to create a guide on how to be a great boss to yourself, I enlisted your help!

A guide to being your own boss and loving itI asked my email list a couple weeks ago – What makes a boss crappy – or great?

(By the way – are you on my email list?  It’s a great place to be.  Why not hop on now while you’re thinking about it?  I’ll send you a heartfelt note now and then, let you know when new posts are up, and keep you posted on any upcoming great deals. Like my Privacy Notice says, you can unsubscribe anytime.)

Pretty soon I had a couple hundred new emails, and I got lost in your stories.

The same themes – and even exact words – emerged over and over.

Let’s look at what makes a terrible or great manager of others, and see if we can apply that to managing ourselves.

1) Terrible bosses focus only on what you’re doing wrong.

One person wrote that their boss would “call at the end of the work day to make sure you didn’t leave 5 minutes too early, but never thanked you for staying late or getting in earlier.”

Others said they had bosses who gave about one compliment for every hundred criticisms.  “No matter what I did, he’d ask about the thing that was missing.”

Do you ever do this to yourself?

Confession – I have a habit of ignoring the work I accomplish, even if it was at great effort or sacrifice, and tend to focus only on what still needs to be done.  Or I’ll bend over backwards to do something especially quickly and well, but not usually high-five myself at the end.  Instead I just think “well that is how I should do everything – why can’t I do this all the time?”  I tend to treat accomplishment like a default state where I should always be.

I don’t think this is healthy – certainly we have to do our work, but we can create hamster wheels where we’re forced to run faster and faster but only seeing the undone in front of us – never pausing to look back on what has been achieved and feeling good about it.

Critique is helpful and necessary (we’ll get to that), but good bosses balance critique with pauses to take satisfaction in jobs well done.  We’d do well to apply that to our self-talk as well.

self-employment-be-own-boss-23372) Terrible bosses MICROMANAGE.

I couldn’t believe how many people used this. specific. word.

The overwhelming consensus:  When a boss hovers and inserts themselves into every detail, it’s extremely stressful, it slows you down, and shows a dispiriting lack of trust.

Is it possible to micromanage yourself?  I asked my friend Jess Rotenberg what she thought, and she had a great observation:

“I think this qualifies:  You find a new course and sink your teeth in. Then you suddenly set up some unrealistic goals and corresponding lists and feel like crap when you can’t “blog every Friday at 8am, shoot a personal project every month, keep your books in line each weekend, read a book on business for 30 minutes each night.”Like a boss who micromanages, you are not allowing yourself to prioritize or do the thing that feels good in the moment. Sure, everyone needs to buckle down and do the hard stuff sometimes. Duh. But we owe it to ourselves to be flexible and choose whatever of three tasks is equally urgent when we sit down to work.”

When you berate yourself for not getting things done in a certain sequence in a certain order, or try and impose too much rigidity on self-improvement practices, it’s similar to micromanaging.

Set high expectations for yourself and follow through – but trust yourself.  Your body has pain to prevent you from pushing too far and getting injured – and your mind is the same way.  Allow for flexibility and self-pacing.

3) Terrible bosses set you up to fail.

One reader said she had a boss who would send her away from her actual job to go clean a warehouse, then would dock her for not having clean clothing when she returned.

WHAT?  You can’t expect people to do what you ask, then get mad about unavoidable results.

But it’s possible to do that to yourself, too.

You can’t decide to double your client load, stay up late getting it done every night, and then get mad that you’re too tired to get up at 6am to train for a marathon.

You can’t say you want to get through 137 educational courses this year, but you only really have 2 hours to devote to study per week.

Set yourself up for success.  Reverse-engineer your goals, plan ahead for slip-ups and failures, and create support systems for new practices.

If you find yourself falling short of something (say, your marathon training), don’t rush to scold yourself – try first asking whether you might be falling short because you’re pursuing something else that you also want.  

self-employment-be-own-boss-23494) Terrible bosses throw their workload on others.

Several people mentioned that their bosses would make others do their work for them, often throwing it on them at the last minute.

At first I didn’t think this was applicable to us.  But maybe it is.  When we habitually procrastinate, aren’t we – in a way – throwing our work on our future self?  Is that good management?

Interesting to chew on.

5) Terrible bosses treat mistakes like the advent of the apocalypse.

“Fear of making a mistake made it nearly impossible to do my job,” wrote one reader.

Another said “I had a boss who was so afraid of his boss and so afraid of making mistakes that it froze our whole unit…It caused our whole area to be laid off and reorganized, because outsiders were tired of his stalling and fear.”

How do you handle your mistakes? 

Do you bang your head against your desk, spiral into despair, or disparage yourself?  Do you freeze in place and refuse to proceed until you’re sure you can do it perfectly from here on?

Or do you take note, make amends where needed, but acknowledge – as one reader wrote – “that mistakes are a part of life”?

Accept responsibility, but accept also that errors will happen.  You will do more that way than if you judiciously avoided all possible missteps.

So we’ve covered a few things about terrible bosses.  Now, on the other hand…

self-employment-be-own-boss-23366) Great bosses are clear about what they want from you.

When a boss doesn’t clearly communicate their expectations, it creates a cloud of confusion and procrastination.  “Am I supposed to handle X?  Or will they get mad at me for working on it because I should do Y instead?” 

You’ll feel freer and more in control if you’re clear about what you want from yourself, too.  What do you want to achieve in the next 12 months?  What does that mean for this season, this month, this week?

Writing down goals and their next steps can give you initial jitters (and might mean confronting limiting beliefs), but it eliminates a lot of questions about what you should be doing, and the vague guilt that you can’t be doing 20 things at once.

7) Great bosses are specific with constructive criticism.

An ineffective boss will say, “This is all a hot mess – you haven’t gotten this right in weeks and I’m disappointed in you.”

Globalizing, emotional explosions like this do happen, but they are pretty useless when it comes to fixing anything.

A great boss will say something more like, “It’s vital that every client initial all the paperwork so we can confirm that they read and understand each item.  When you neglect to do that, it jeopardizes our business and their good experience.  So moving forward, it’s important to make sure that they do it each and every time.  I know you can do this.”

You can’t do something correctly until you pinpoint exactly what has gone wrong.

When you mess up, figure out exactly what needs to change, and say “I know I can do this next time.”

8) Great bosses are generous with praise and rewards.

One person said, “A little pat on the back once in a while is so valued by employees.  Just a paycheck is not enough to keep up morale.  I’ve had employers who did this in spades with parties and bonuses and lunches out.  I’ve had employers who sucked at it by pretty much ignoring me.  Little things that say “I value you” are not only appreciated, but necessary as far as I’m concerned.”

We’ve covered positive self-talk in moments of difficulty – but do you ever go out of your way to just say to yourself “Hey, thank you for doing this work”? 

Or, “Remember that one time a few months ago?  You got through that, and now look at all the good things that have happened.  Keep it up.”

Give yourself small bonuses for work well done.  Take yourself out to lunch.  Or to the library, park, or forest.  Get a $3 bunch of flowers for your office.  It doesn’t have to be expensive, but it should be tangible and designed to say “hey, great work.”  (No, the whole-family vacation you already have on the calendar isn’t really the same thing.)

self-employment-be-own-boss-23359) Great bosses have high expectations

Someone said that their boss “pushed me to handle issues I was a little scared of.  She was supportive, but firm that I needed to learn to deal with things on my own.”

Another person wrote that their boss was supportive, but also “Set a high standard and expected me to go beyond that.”

So what’s the difference between setting a high standard and setting yourself up to fail?

Part is planning, and part is the way you handle mistakes.  If someone says “I know you can do this – or even better!” and reacts to slip-ups as normal learning experiences, it becomes a delicious challenge that infuses you with motivation.

10) Great bosses respect life outside of work.

Special holidays, family events, sick kids, broken-down cars – life happens.  Good managers don’t freak out if you have to step away for a day or two, they set up their business to plan for occasional absence.

What about you?  Do you have protection clauses in your contracts that outline what happens if you get sick?  Do you have an assistant who can answer urgent emails for you?  Do you allow yourself to step away to see your kid’s play without feeling guilty?

You also aren’t an automation who exists to work under all but extenuating circumstances.  

This one is especially hard for high-achievers or entrepreneurs, but rich lives have many facets.  When you get satisfaction from work, it’s hard to remember to take breaks or cultivate other interests.  Maybe you don’t even want to at first.

But take breaks you must.  You need rest and variety to re-gather inspiration.

Also, you identify mostly as a business owner, then any failure on the job can feel catastrophic to your sense of identity.  But if you think of yourself as a business owner, parent, gardner, avid chef, sister, aunt, friend, volunteer – then any failure feels correspondingly smaller and more in perspective.

So set a clear number of work hours and stick to them.  That’s not micromanaging either – it’s creating healthy boundaries to protect your ability to work.  When you work too much, resentment sets in and creativity dries up.

In the words of a reader:  “Well-balanced employees are happy and productive employees.”  

And, lastly,

11) Great bosses have high levels of trust.

One reader sent this effusive note about her bosses in an ice cream shop:

“They trust us.  They let us create crazy homemade ice cream flavors, design t-shirts, and even paint on the walls.  HOW LUCKY ARE WE?  (The answer is so lucky.)  How many people do you come across that give that much liberty to their employees?  I can tell you we have the most excellent customer service because we employees are taken care of.”

Here is what I know for sure (thanks for the phrase, Oprah):  Human beings have incredible ideas and gifts.  If you give them freedom, materials, and a few clear guidelines, they will build you amazing things you never would have thought to ask of them.

The best answers I’ve gotten from any of my independent contractors has been in response to the question, “what do you think we should do?”

My advice to you is – learn all you can, study success, but in the end, trust yourself.  All of this knowledge you acquire does not constitute a grand “must-do” blueprint.  It is all raw material from which you should feel free to build your own never-before-seen creation.  Trust your ability to solve problems.  Trust your ability to react well.


How else do you think you can be a good boss to yourself?

Do you see any more applications or parallels between good external and internal managers?  Let me know in the comments!


This post is part of a series called

Get What You Want This Year.

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  1. Nathan Tsukroff on March 31, 2016 at 11:09 am

    What a wonderful article! And just when I am addressing my self-doubts! Thanks for this great guide to finding balance as my own boss.

    • Jenika on March 31, 2016 at 3:27 pm

      Thank you, Nathan! I hope that something here helps you moving forward. Keep clicking!

  2. Nicole Begley on March 31, 2016 at 12:16 pm

    Jenika – You hit this one out of the park! LOVE everything about this!!

    • Jenika on March 31, 2016 at 3:27 pm

      Thanks Nicole! I’m so happy to hear that you enjoyed it 🙂

  3. Chrissy on March 31, 2016 at 4:52 pm

    What a great article. I enjoyed it greatly. and I love your content.

  4. Juan Martin on March 31, 2016 at 5:05 pm

    What a wonderful post, Jenika! It actually hit me hard and made my eyes wet. Most of the time it is so clear for us that we do not let anyone, specially our bosses, to mistreat us but not so often we reflect on how we treat ourselves. Thank you so much!

  5. Misty Bradley on March 31, 2016 at 5:17 pm

    Jenika, another great post! I shared it with the Being Boss podcast FB group (almost 10,000 members) and lots of photographers. I’m also going to share it with our “we are the REVELERS” podcast listeners. You will be helping lots of bosses today! You’re brilliant!

  6. Daisy on April 1, 2016 at 11:16 am

    Jenika, this is so good! When you asked us all those questions, never would have thought this was the angle you were going for. Saving this to reread. 🙂

  7. Cheryl on April 4, 2016 at 3:20 pm

    Oh boy! This really helped me think about what I’m doing as my own boss and recognize areas of improvement and affirm areas of strength. Thank you for this enlightening article!

  8. moi du toi on April 17, 2016 at 7:56 am

    VERY well said! I seem to be such a hard taskmaster to myself, all criticism and no appreciation for how far I’ve come and what I’ve achieved. Thank you for the wake up call Jenika and those gorgeous daffodil images.

  9. Sara Finazzo on October 14, 2016 at 6:48 pm

    I just recently came across your site and I love it! Thank you SO much for the awesome content! Please keep this up, you’re changing lives! 🙂

    • Jenika on October 14, 2016 at 9:23 pm

      What a kind comment. I’m glad you’re here!

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