Strategically Setting Milestones

Rather than focusing on the big milestones, celebrate the many wins along way.

When you first start your business it can be a very exciting time. As the days, weeks, months and years roll by, and you are slaving away to meet your big lofty goals and ultimately become successful, motivation can wain. Energy can drop. Morale can sink. In this post I’ll dig more into this topic and how strategically setting milestones can help you achieve the really big ones.

Starting your own business requires a lot of all of these: motivation, energy, morale. And yes, at the beginning they seem abundant. It’s like starting out on a long voyage at sea. When you first leave the dock, you have everything you need. But the hard work along the way can tap your reserves and leave you wondering if you have enough to make it to shore – your big goal.

How can you make sure that you don’t peter out or completely lose steam along the way? How can you make sure you’re not left dead in the water?

By strategically setting milestones along the way, you can give yourself a boost along the way. Achieving a smaller goal is like catching a fair wind and gaining err…ground doesn’t quite fit this analogy but you get the point.

If you embark on this voyage, know fully the amount of work involved.

Don’t be the five year old entrepreneur yelling are we there yet from the back seat. Be the captain of your ship, create a checklist and milestones.

A sea captain sets multiple dates, and milestones to have reached throughout the voyage. By XXX date we should be here, and YYY date we should be here. Your entrepreneurial journey is similar.

When I work with my clients, we strategically set milestones for branding, content marketing and client acquisition. This way we have many small wins to celebrate along the way. Really honing your branding with a solid positioning statement – Yes! Developing client personas – now you know where you’re headed! Outlining a content calendar and plan for generating the multiple pieces – outstanding, you’ve plotted your course!

Bumps and Missed Milestones

Being an entrepreneur is great – but it’s not all blue skies and fair winds. There will be times when we hit bumps in the road or miss our strategic milestones. We’ll lose deals, fall short. And that’s okay. In fact, the only time that it’s not okay is when you let it defeat you.

When something negative happens, I used to beat myself. I wasn’t rational. Clients come and go. Deals are won and lost. If there was a law of nature for business, this is it. The problem occurs when we can’t see past these upsets. It becomes that much harder to work towards reaching your lofty goal, which is why having one much closer is imperative.

I had one client who sold his business – literally he was no longer my client anymore because he was no longer in business – and I was beating myself up over it. The new owner, is married to someone like me, a professional marketer and business owner. There is no way in hell that he was going to keep paying me to do what his wife could do. Yet it still stung. Why am I telling you this? Why am I embarrassing myself? If we all sit down, we have a story like this. It’s human nature.

And when these situations happen, because believe me, they will, it’s nice to have a positive achievement, a met milestone close at hand. If starting your business 3 years ago was the last thing you celebrated, one failure is all it might take to break you and make you throw in the towel.

Don’t believe me? Believe Science and the Experts

In his book, The Messy Middle, Scott Belsky devotes precious space to this concept. He calls it short-circuiting your reward system. Scott quotes another author, Monica Mehta and her research on brain chemistry and its effects in entrepreneurship. I highly recommend Scott’s book and I definitely plan on spending more time with Mehta’s works.

Remember in school when they taught you about those feel good chemicals? The ones our brains release when good things happen? Well, celebrating a win is a good thing. When we “win”, our brain is bathed in these feel good chemicals. When we lose, not so much. As kids, we are trained to seek out these positive feelings celebrate our achievements, no matter how small.

The trick is not to lose this as we become entrepreneurial adults. Adventurers and explorers had (and still have) a childlike fascination with the world and so must we. Within reason, we must take a look at the road ahead and plan out stops or accomplishments along the way.

Recently I was quoted on this topic in an article by Best Company on how to reboot your motivation for new years resolutions in business. You can read the full post here.