How do you define success milestones and celebrate accordingly?

Dani Sampson
Mar 27, 2019 · 5 min read

The measure of success varies from person to person, from job to job and task to task.

Yet, when we’re always looking to the next line item on our never-ending ‘to do’ list — how do we measure our success and celebrate it both personally and collectively?

I’ve suffered lately from seeing ‘down time’ as wasted time. Some would say I am a workaholic, because even in moments where I binge watch Netflix, I find it’s in the searching for distraction. That I am still using ‘entertainment’ as a tool to escape productive thinking rather than fully embracing rest.

Starting a business comes with sacrificing some peace of mind. There’s no pay cheque hitting your bank account weekly, fortnightly or monthly. There’s no manager to set your objectives and to tell you when you’ve done a great job or when you need to improve.

You become a free agent; setting your own tasks and constantly worrying whether you’re doing enough to succeed. Add a bit of family funding or venture capitalism and it all feels like borrowed time. Time in which you’re indebted to reach a return on investment.

So, when is it okay to settle into quiet periods of ’true’ regeneration, not just a bottle of wine or a six pack of beer to decompress from another day of pushing shit up a hill? When is it okay to tell yourself you’ve done well and that you ‘deserve’ a break?

We can only measure our success if there are mapped milestones. Whether that means being closer to a desired mental state or tangible to-do’s. I wish I had articulated my professional and emotional milestones better, with as much foresight as possible from the beginning so I could have given myself more permission for self-kindness.

Wish I’d celebrated the first step in the right direction, the leap away from full-time work. When I engaged a design consultant, saw my visual branding for the first time, launched my website, submitted my first client proposal, published content, had prospective client meetings, received my first work deposit, made it through many months without going broke, being kicked out of my rental property or having serious thoughts about throwing in the towel.

I distill business goals for a living, but when you’re starting up alone, there are smaller more intricate moments that need to be noticed and celebrated. It’s contradictory, because the aforementioned moments for me have only been appreciated in hindsight. We just need to get better at recognising them along the way without a dedicated plan to self adulate when needed for our mental and emotional health.

Because the reality is, there are so many moments of self doubt that dampen our potential, but they also fuel a fire within us to do better — to be better. The best way to reconcile the reality of suffering and sacrifice is to balance them with self love and positive recognition.

When you truly embrace that feeling of a milestone reached, you can settle into yourself long enough to enjoy those small wins.

Rather than living with the perception of hard work being coupled with running ourselves into the ground, why not work hard and reward hard? Rewarding yourself not through substance or consumerism, but through the gift of relief.

Photo by Matt Messiha

I’m reminded to reward myself through a few avenues of personally-perceived validity:

The first is recognising progress toward a goal.

We can get hung-up on analysing our goals through a microscopic lens. The progress between yesterday and today may be indistinguishable whilst entrenched in the action, but every step made in pursuit of a goal is meaningful.

We can also forget to reward ourselves for our breadth of accomplishments. Where I was a year ago is leaps and bounds from where I am now. Through widening the lens a little, I am able to scrutinise myself less and reward myself more.

The second is knowing what recharges your batteries.

Sometimes we escape to survive. When we put our eon-old human reflexes to good use, choosing to run rather than confronting our struggles and achievements alike, we are actually lending ourselves to short-lived distractions. In the practice of distraction, not only do we miss the scary and dangerous feelings but also the feelings that see us name our achievements and celebrate them with pride.

Leaning into my obstacles rather than pulling away has allowed me room for reflection. Not so long ago I swapped ‘escapism’ out for ‘retreat’. Whether it comes in the form of a weekend camp with friends or a yoga session, retreat allows me the time not to tune out, but to tune in, to be present, reflect to a point where I’m okay with my current state of existence, recharge in a healthy environment and finally recover.

Photo by Matt Messiha

Lastly, acknowledging the beast in the room and making space for gratitude.

I’m reminded of my mother telling me that I’d ‘created my own beast’ in an entry level job many years ago by biting off far more than I was even asked to chew.

Striving for greatness beyond complacency is a worthy endeavour to those who value it. Recognition of circumstance however should be valued equally. Because in most instances, this first world privilege to ‘create our own beasts’ means most of us have a roof over our head and food in our bellies. Enough fuel and enough safety to strive should instinctively recall perspective into our own lives.

Nobody really likes to think about how messed up some parts of the world are; how hungry, how war-torn, how poor, but the reality is that whatever is going on with my business or my internet connection or rent is actually a blip on the world-scale of human problems.

When things become tough, I recall the practice of showing gratitude for what I have, how free and incredibly lucky I am. This gives me unparalleled resiliency, motivation to aim high and most importantly to quit complaining and be proactive in mending problems.

And, mending a problem or two usually leads to more milestones that need to be celebrated — so, give yourself a pat on the back and keep doing what feels good, right and worthy for you.

If you need help planning your business milestones, I can be found here

The Startup

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Dani Sampson

Written by

As a Brand Strategist I am a professional problem solver, a corporate counsellor and a creative curator. I am here to connect the dots.

The Startup

Medium's largest active publication, followed by +565K people. Follow to join our community.

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