Camp Challenge: Describe Your Dream Boss

Camp Challenge: Describe Your Dream Boss

Pattern by Joyful Roots for OMHG


A few weeks ago during an OMHG Twitter chat, Jessika prompted our discussion by asking:

How can we be better bosses & set ourselves up for maximum awesome (however that looks for you)? #omhg

In creative business you wear many hats, and the most important one is the “boss hat.” Therefore, it’s important to work up a dream boss description (similar to the ideal client exercise), listing all the things you love and appreciate about the boss you wish to be.

The Challenge: Describe Your Dream Boss

Setting and achieving goals requires that you adopt some new habits. It means following a production schedule and keeping yourself on track. This is, by no means, an easy task. However, to grow, expand, and present your business in a bigger, better light, you have to strengthen your will-power, increase your productivity, and eliminate any unconscious self-sabotaging ways. And since you’re your own boss, please try to do this in a gentle and understanding manner.

In fact, before you set off onto your biggest, wildest dreams, write up the definition of an ideal boss. What is she (or he) really like? How many vacation days does she give you? Does she give you a Christmas bonus? And if so, for how much? Does she surprise you with early releases? Host happy hours for the office? How does she treat you when you’re sick and need the day off? How does she respond when your family needs you, and you know that being with them is more important than anything else you could do that day? How does she react when you do a good job or exceed her expectations?

Please take the time to write her down and describe her in great detail. Post that in your workspace where you’ll see it often …

And then, BE HER (or him!).

Give yourself permission to grow into this job. Remember why you’re here and who you wanted to be when you started. There’s a lot of work to be done, but remember, the only way to do it is by taking it one step at a time.

As a group, we took on this challenge inside the Oh My! Membership Community. Here’s what our members had to say about their dream bosses:

My dream boss encourages and expects me to grow and improve over time, not overnight. I’m only 10 months into my business, yet I’ve already put such impossibly high expectations on myself. I see other successful businesses and feel like I need to achieve their level of perfection in order to stand alongside them as a creative entrepreneur. Now that I have a dream boss, she’s going to cut me some slack, give me credit for how far I’ve already come, and lovingly encourage me to continue to improve. Besides, who’s perfect anyway?!

My dream boss doesn’t give me the guilt trip! This is by far the thing I was most excited to leave behind with my day job. I have more health issues than most (in comparison to my past co-workers at least) and I dreaded the guilt trip that came more often than not when I wasn’t able to come to work. And somehow, I’ve wound up yet again with a boss who makes me feel guilty when I set aside work to focus on what matters most. It’s definitely time to become the kind, understanding dream boss that reassures me it’s okay to put my family, my health, and my friends first sometimes. Because when I do, I’m “setting myself up for maximum awesome!”

– Anne, Totally Design

My dream boss understands that a productive work day isn’t always 9+ hours in a row, Monday through Friday, and will allow for varying work hours in order to complete my best work. She values a strong work ethic that is balanced by a strong health ethic, and knows that working me into the ground may produce one good result, but it’s not sustainable (or desirable!).

My dream boss speaks honestly and clearly, leaving little space for “but what did she mean?” and “I didn’t know you meant this when you said that” and “but that’s not what you said yesterday”. She believes in the power of hugs, high fives, and “job well done!”. She also believes in the power of failure, mistakes, and lessons learned without the attachment of negativity and guilt.

– Melissa, Print Therapy

My dream boss values me so completely, that she NEVER forgets why I agreed to take this job in the first place: So that I could work flex hours and put my family first while honoring my creative nature and entrepreneurial spirit at the same time.

She knows that I’m a mother of four and wife first, everything else second, and that being present for them is more important to me than all the stars.

And when I’m with my dream boss, she brings out the best work I can possibly produce. She encourages my big leaps and hops onboard my never-before-seen ideas. When I feel anxious to share a big dream (afraid of criticism or failure), she clears the room and opens up space to explore its pros + and potential. I love that about her.

– Lisa, Marketing Creativity

My dream boss is aware of my capability and always pushes me to try new things and work harder, and would constantly tell me that she believes in me. She is supportive of me as a person, mother, and employee and values my needs and opinions. She values my experience and encourages me to keep learning and acquiring new skills.

She invites companionship among colleagues. She believes that a community-like work environment where employees feel safe to be themselves, share their worries, concerns, professional opinions, and personal trials and victories. She believes that everyone brings something extraordinary to the table, and that no one is anything less than an amazing asset.

And my dream boss certainly knows my son and my husband are my number one priority.

– Cody, Lu & Ed

My dream boss provides a fun and attractive work space where I feel safe and happy and is consistently motivating and encouraging. She provides me with the correct equipment and materials for the job, and celebrates and praises my accomplishments – both big and small.

Debra, Stitching Rules

That’s what a dream boss looks like to us-in the comments, please share what a dream boss looks like for you to be included in Part 2 of this post!

Leave a comment sharing what your dream boss looks like and one link to your business or blog, and your response could be featured here next time! 


  1. Megan S says:

    My Dream Boss

    Recently after a few minutes of listening to ramblings about past bosses I joked to a friend it sounded like we were describing TLC’s new Reality Show “How Not To Be a Boss!” I asked what she would want different in a boss when she went back to work and then our conversation was cut off and we moved on with the rush of a drive thru or something equally as important. This question is timely, I can finally answer my question and move to a better Reality Show… “This IS your Dream Boss!”

    After thinking, no dreaming, about my perfect boss I realized that my dream boss could be summarized in the following 5 qualities:

    1) My boss is committed to the mission, vision and values of our organization and communicates them clearly with passion. They understand the company goals and financial objectives and how my specific role impacts the outcome. As an individual my boss is committed to their individual job and cares about what they do. My boss is committed to my professional development and to me as a part of the organization.

    2) Openness is often times undervalued in a leader. My boss understands the world is changing and is not afraid yet anticipates what the future brings. My dream boss challenges others to be part of the process, requires constructive feedback, is adaptable and demands a supportive environment. We are allowed to feel connected to the process and take individual responsibility for our work as this is a feeling we crave.

    3) An effective boss is action focused. They understands peak perform occurs when moving towards a common vision. An intentional leader equips their team with the process so they are effective with their jobs. Leaders provide redirection when a team is off course realizing that the recovery process and lessons learned are valuable for growth.

    Through action my boss provides accountability. Once a positive environment is established and training has been provided, productivity and enthusiasm will disintegrate within the workplace if the non-committed and non-performers are not held accountable for their actions and outcomes.

    4) My ideal boss understands the power of communication. In a fast paced world where we are inundated with many technological devices and many responsibilities and still 24 hours in a day how my boss communicates is as important as what they communicate. How my boss communicates? Authentically, honestly, with respect, in writing and verbal. What my boss communicates? My boss communicates vision, provides resources, elicits feedback from customers, provides constructive criticism, encourages, praises, brainstorms options and is supportive. I don’t think I am asking for too much.

    5) Balance in a boss is imperative. My boss has fun, adventurous, rewarding, challenging, tiring, stressful and exhilarating all at once. My boss knows that sometimes you need to have fun. There is a definite time to be focused and work tirelessly and then you need to pull everyone together to breathe and release. Those moments will commit a team together so you can accomplish anything!

    Here is the casting call listing for My Reality Show,“This IS your Dream Boss!” This person is a not only a Boss but also a C.O.A.C.H!
    Action Focused
    Has Fun

  2. I like what Cody says – “She invites companionship among colleagues” The people you work with play a big part of your enjoyment of the job and can be overlooked by many employers. Great exercise Lisa. I’ll be revisiting this one again in the future.

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