Entrepreneurs: Don’t Be Your Own Dick Boss

Today we’re going to talk about horrible bosses…I don’t mean the horrible bosses that may have helped drive you to pursuing business ownership, however, because the worst of the worst when it comes to bosses is usually you.

Yup; in my experience working with entrepreneurs, we are horrifically bad bosses to ourselves, and we’re not doing ourselves any favors by being that way. Let’s pretend for a moment that our boss selves as entrepreneurs are separate from our worker selves and dissect why we suck so badly.

Imagine you were still in the corporate world and your boss expected you to be able to move heaven and earth at a moment’s notice or she didn’t pay any attention to what you do and let you get away with anything but then told you you were a terrible employee later when you didn’t meet revenue goals; or maybe she wanted you to be on call every second of every day with no down time and no vacations; maybe she refuses to invest in any professional development for you or any of the resources that would help you succeed in your role but then compares your performance to others who’ve had hours of training and whose companies provide them tools to get things done more efficiently, perhaps she pinches every penny and doesn’t let you travel or treat potential clients to lunch but expects you to close at a rate like those with huge schmoozing budgets; she also might never provide you  with clear goals or strategies for reaching those goals but then be angry when things aren’t getting accomplished; and when you do succeed or do something really well, she never gives you the praise or credit you deserve; in fact, she might even regularly call you stupid, lazy, irresponsible, not a real professional, or any number of nasty, insulting names.


Clearly, this would be the boss from hell if you worked under her at a big company but, since I told you where I was going with this from the very start, I’m sure you can see that these are all things that we entrepreneurs do to ourselves regularly, and we’re sabotaging ourselves by doing so. Just as you wouldn’t be able to do your best work and you would burn out quickly under the devil of a boss that I described above, you’re not going to be able to achieve as much as possible with your business and stay motivated to keep building it if you treat yourself this way.

So here’s what you need to do, starting immediately:

#1: Set clear goals and develop strategies to achieve those goals. You need goals, you need steps to reaching those goals, and you need deadlines for hitting milestones along the way

#2: Stop talking ish about yourself. I’m as bad as anyone with calling myself names when I haven’t accomplished something I intended, or I’ve been a bit lazy, or something didn’t turn out as well as I’d hoped. I get how easy it is to have that negative internal dialogue, but, starting today, you need to agree that if you wouldn’t say it to an employee, you can’t say it to yourself and if you wouldn’t tolerate being spoken to a certain way by your boss, you have to stop talking to yourself that way.

On the flip side, however, #3 is hold yourself accountable. Usually the crap talk about ourselves comes because we’ve failed to do something that we were supposed to do because we don’t treat our deadlines like real deadlines or always do our best work because, “Hey, I’m my own boss so what’s gonna’ happen?”

Well, what’s going to happen is your business isn’t going to live up to its potential and you’re going to be disappointed in yourself so, when you’re setting your goals and milestones, also set up consequences for not reaching them. Maybe you don’t get to go on your girls’ weekend if you haven’t finished next week’s blog post or you have to treat someone to a really expensive dinner if you don’t send out that prospecting email…do whatever works for you but make sure that there is a consequence if you don’t accomplish what you say you will accomplish – a real consequence, not you telling yourself how dumb or lazy you are.

And finally, #4 is give yourself the tools you need to succeed and reward yourself when you do something right. Don’t let yourself get sucked into a training circle where you just constantly attend trainings and webinars and never actually get to building your business, but if you don’t know how to do something well, you have to go learn how to do it before you can use it to grow your business and if you have a lot of balls in the air that you’re juggling – and what entrepreneur doesn’t? – you need to rely on some tools to help you streamline everything and get stuff done. Sometimes those tools and trainings cost money that you won’t want to spend, but you need to objectively weigh the costs and benefits and make rational decisions about what to invest in instead of just pinching every penny if you want to succeed. You also need to give credit where credit is due and reward yourself when something goes really well . Don’t go buy a Ferrari because you landed one client, but a massage is probably well-deserved if you accomplished a lot for your business this week.

Just remember, we’ve all had terrible bosses before and the lucky amongst us have also had a few fabulous ones, so when you’re dealing with yourself in your business, think about what a great boss would do and emulate that and if you catch yourself behaving like a boss from hell, take a step back and get your ish together so you can get back on track with properly managing your business.

If you’re an aspiring entrepreneur, the best thing you can do for yourself is to just get started. Pick up my business planning ebook here to be guided through the whole business planning process for less than $5.
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