Be Your Own Best Boss: How to manage yourself when you're the CEO

LK Consultants regularly seeks experts in their field to help bring additional value to readers of The LKC Blog. Please enjoy today’s special guest post by Allison Krawiec-Thayer.


It’s been 2 years since I left the corporate world to “be my own boss.” This time has been full of colorful Google docs, imposter syndrome, events no one came to, events everyone came to, self-doubt, rebranding, countless freebies, a full-blown mental health crisis... all that to say, it’s been a lot. 

As an entrepreneur, specifically a solopreneur, I’ve had to have my own back through all of this. Sure, there is tremendous freedom in not having to run ideas by another person, but the tradeoff is having to do this alone. 

I, like many entrepreneurs, find ways to invite others into the parts of the process that can be shared. I seek out feedback, advice, motivation, and support from others. Ultimately though, my decisions about my business are my own and I need to trust myself to make them.   

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One day, while standing mid-embrace with my spouse in the kitchen of our San Francisco apartment, I had a jarring realization of clarity. I stepped back, stared at him and said, “You’re.... my principal investor.” (We’re both growth hacking nerds embedded in startup culture, so oddly enough, this is how we talk to each other.)

Maybe the hug triggered my feeling supported? Whatever the reason, I realized that he was bankrolling my life so I could start this business. I could have a steady job with a paycheck (SF would be way easier with another income...), but we decided together that I would start a business. 

My realization continued: “If you’re the principal investor… I’m the CEO. Ho-ly crap. This is a real business. I have a real business.”

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Prior to that moment of CEO-realization, I had an expensive hobby that wasn’t helping anyone. Seeing myself as the leader of a company changed everything. 

As entrepreneurs, we don’t have a weekly 1:1 sync with our manager asking us about progress and roadblocks. We don’t have a built-in support system for when we aren’t as successful as we’d hoped. One of our roles as CEO is being our own managers. Read on for my tips and a sample agenda for running a 1:1 with yourself.  

1. Set yourself up for success by having a plan and reviewing it weekly (or 2x month)

The unstructured nature and freedom of entrepreneurship is appealing, but if you want to get anywhere, you need some kind of plan to stay accountable. Set some goals and break them into 6 month, 3 month, 90 day, 2 week, and/or daily tasks. 

Start your 1:1 with yourself by reviewing this document. 

Consider asking yourself some or all of these questions: 

  • Am I still feeling in alignment with these goals? 

  • Am I on track with my deadlines? 

  • What is getting in my way? What could get in my way? 

  • How can I overcome that challenge? Who do I know that might have advice? 

  • How may I set myself up for success this week? 

2. Look for growth opportunities

On-going personal and professional development are critical for leaders. To keep our creativity and innovation alive we need to learn, expand, and challenge ourselves continually (much like a manager might). Maybe this is finding opportunities to bring people together for events, starting a newsletter, or picking up a new skill like podcasting, coding, or SCRUM.  

Dedicate the next 5 - 15 minutes of your 1:1 looking for, or providing yourself updates on, growth opportunities (keep track of action items and follow up at your next 1:1).

3. Protect your mental health  

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Lastly, and most importantly, we must be our own managers in regards to mental health. Sometimes entrepreneurship looks like working hard on something that doesn’t gain traction, hanging on to projects that no longer excite us, or jamming our schedules to keep up with the “busy” facade. It is important to check in on ourselves to make sure entrepreneurship is still full of the fun freedom that attracted us in the first place. 

Dedicate the final 5 - 15 minutes of your 1:1 to examining your mental health and how you are experiencing your business.

Consider asking yourself some or all of these questions: 

  • How have I felt over the past week or two in regards to working?

  • On a scale of 1-10, how close to burnout am I? 

  • What activities are keeping me from burning out?

  • What activities are burning me out?

  • What is one activity I can schedule to support my mental health this week?  


Entrepreneurship is the most challenging and rewarding thing I’ve ever done. Having your own back makes the journey way more fun. Try implementing 1:1s with yourself and at the very least you can buy yourself a “World’s Best Boss” mug.


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About Allison Krawiec-Thayer:

Allison is a certified professional coach, human sunbeam, and founder of PoppyLead -- a leadership development company working with entrepreneurs, managers, and leaders who feel out of their comfort zone. She loves spending her days helping people uncover their unique leadership strengths, playing Settlers of Catan, and chasing her rescued Tijuana street dog through their Denver backyard. 

She also bookmarks way too many Medium articles, has 24 tabs open, and recently launched her quarantine-induced virtual talk show experience, Confidently In Charge!