Creating Benchmarks When You Don't Have A Boss

Three years ago, my family, friends and colleagues gathered on a patio on a warm spring evening to celebrate the 5 year anniversary of my company.  I’d spent many days and sleepless nights anticipating what it’d feel like to make it to 5 years, largely due to the conversations I’d shared with my father since I’d started my business.  Every time things had gotten difficult for me (which was often, let’s be honest), my dad reminded me about an important statistic: “All you have to do is make it to 5 years.  Most businesses don’t make it to 5 years and when they do they’re 85% more likely to succeed”, he’d say.  It should be noted that his percentage ranged anywhere from 60% to 99% each time he gave me this advice, in direct relation to how upset I was.  So over the years, I held on to this magic number, sure that once I’d made it to 5 years I’d feel confident, stable, and successful.  Each time we came in over budget, lost a potential client, or struggled to properly manage our staff I thought, “When I make it to year 5, everything will be 60-99% better.  Just hold on.”  However, on the night of my 5 year anniversary party I felt far from confident, stable and successful.  In the months leading up to our anniversary, we faced a financial blow that nearly put us out of business, one of our most valuable team members was on the verge of quitting because we could only barely afford to pay her, and I was nearing burnout, still working 15+ hours per week for other companies just to make my own ends meet.  

Mid-way through the evening my dad pulled me aside, put his arm around me and said, “well kid, it’s smooth sailing from here!  You made it to year 5!”.  My stomach turned.  ‘If he only knew! We’re failing!’, I thought.  

Despite hitting this benchmark, and many more over the past 8 years, I can’t seem to quiet my internal ‘if they only knew’ voice.  There’s some truth to my dad’s 5 year promise, but I’ve learned that it’s not because hitting the 5 year benchmark means you’re necessarily out of the woods.  Your business is more likely to continue succeeding if you make it to your 5th year because it usually means you’ve gotten through enough tough times to begin trusting yourself, to solve problems effectively, and to make the right kind of practical decisions.  However, these aren’t accurate benchmarks for experiencing the feeling of success.  

In Ben Horowitz’s brutally resonating piece, he suggests that a key defining factor of a great CEO is that they “don’t punk out and don’t quit”.  The most psychologically draining aspect of running your own company, building your projects from the ground up, and watching them disintegrate in sometimes unimaginable ways, is that there’s absolutely no way to tell if you’re successful other than your ability to keep going.  Quite simply, without a boss, there are no pats on the back, promotions, or recognition.  Your success exists in a vacuum, and your failure resonates 10 fold to your staff, clients and partners.  

This is a problem I’d really like to solve for two reasons.  For starters, for those of us who are well suited to the role, having the creative autonomy to watch our own ideas come to life is the single most gratifying experience we can hope to have in our career.  Secondarily (but no less important), I care a lot about teaching kids (students of mine as well as my future children), that carving your own path is sustainable - emotionally, financially, and physically.  And as always, if we’re going to teach future generations about behaviors we’d better learn to walk the walk.  

I started out on the path to solve this problem by assuming the solution was to create many small benchmarks for my business.  I’d write endless lists of grants, clients, staff developments, etc. that would define my business success for the year/quarter.  This was ineffective as I found that every benchmark we reached only gave birth to a new, greater benchmark.  This was super useful in driving my own ambition and growing a business, but not so much when trying to balance my emotional responses. I was still basing my personal experience of success on whether or not my company crossed an item off on a list of goals.  The goal in business is to keep pushing to be more, but our goal as healthy people is to love ourselves authentically, as we are right now.  It’s seemingly impossible to balance our professional need for more with our personal need for contentment.  

Recently, I’ve begun making headway on breaking the professional benchmark cycle by challenging myself to a simple writing exercise.  In the exercise, I opened a blank document and explored what it means to me to be a good founder, not a good business.  I answered many questions including: 

When you say the word founder (or CEO, or whatever your chosen title is) what or who do you picture?  What do they wear? What time do they stop working? What does their home look like? How often do they travel for work?  How often do they vacation?  What do they read? How much time do they spend on Facebook? How do they manage their staff?  How much of their personal life do they share with their employees? How many professional events do they attend in a given week? And so on...

What I realized by the end of the page is that what I was really doing is setting goals about what kind of person I’d like to be, and the kind of person I am exists independent from my list of business benchmarks.  By creating a framework of how to define success based on behaviors, ideologies, and lifestyle, I’d created a powerful way to feel deeply gratified by my day to day work.  

Of course, this is a lot harder to execute in real life than simply writing a journal entry. 

Here are few ways I’ve found to increase the effectiveness of this exercise: 

1. Re-read your own words.  It’s easy to write down a vision of the kind of founder you’d like to be, but it’s much more difficult to re-read your words on a day when you’re struggling to manage a difficult employee or have lost a potential client.  Set reminders to regularly re-read this vision, revise it as you see fit, and keep it in the forefront of your mind. 

2. Track your success.  If you’re doing a good job of re-reading on a regular basis, start tracking your success in these founder areas on a daily or weekly basis.  Is one of your goals as a founder to ask more questions in meetings?  Write a few sentences after each meeting about how you did.  The more you increase your awareness, the more success you’ll have, and the more success you have in these areas, the more you’ll see your business objectively.

3. Take care of yourself.  This one is obvious, but it can’t be overstated.  Know without a shadow of a doubt that your ability to see yourself and your successes in a healthy way is directly linked to whether or not your body is healthy.  That means sleep for enough hours every single night.  Make sure that at least a few nights a week don’t include any alcohol.  Feed yourself food that makes your body feel good.  Move, stretch, walk, be active.  Also, are you breathing?  Make sure you’re doing that too.  

4. If all else fails, start small.  If you’re like me, writing about the founder you’d like to be might be getting mixed up with complex societal, familial or personal expectations.  Start small and try setting benchmarks for the kind of plant owner, grocery shopper, or pet mom you’d like to be.  Healthy habits are a learned skill just like anything else!

Of course, this is still an everyday struggle for me.  My list of business goals remains lengthy and intricate and I’ll always be affected by the successes or shortcomings of my projects.  But nothing feels more important than finding ways to feel good about my work, even when my business is having a bad day. 

EssayDebra Giunta