I found my purpose hiking up Mount Greylock

Path to Purpose

How my hike up Mount Greylock gave me clarity to focus on my dreams

“My route lay up a long and spacious valley called the Bellows, because the winds rush up or down it with violence in storms, sloping up to the very clouds between the principal range and a lower mountain. It seemed a road for the pilgrim to enter upon who would climb to the gates of heaven.”

–Henry David Thoreau

A few months back, I decided to build a brand new wellness venture (more on THAT later).

Running a consultancy full-time and launching a new startup is challenging. So when a very large advertising agency (a business partner) offered to buy my company, I thought, this is perfect! I won’t have to run my business–I’ll be a strategic advisor. I’d be able to focus more time on the startup (or so I thought).

I kept thinking to myself PEOPLE would be so impressed and that became a motivating factor. We’d have big press releases and my days of hibernating would be over. I somehow convinced myself that this deal was the only way to prove myself before announcing the startup. Things were in motion–I had the paperwork…the lawyers were reviewing.

On September 15, four days before my birthday, I woke up and realized I did not actually feel good about the deal.

There were too many conversations with the C.E.O. of the other company, where I had to convince him my company was worth more and I was worth more. They kept adding my personal time into the contingency without more compensation. You know how sometimes you’re on fire and radiate charisma? I wasted one of those days repeating myself over and over to him. The worst part is I had skipped a startup investor conference. Over and over I chose to spend my time trying to make this deal better for me vs. feeding my startup. But…I wanted the “glory,” the press release. The outside validation. But, did I? The deal was starting to feel like a tether to the consulting world, an anchor. Something blocking the path of my dream. Want to know what happens when you spend your days trying to convince people of your worth? You start to feel insecure.

Stepping Away to Gain Clarity

For whatever reason, I kept thinking my life was at a transition point very similar to back in 1995, after graduating UMass Amherst. I knew I was focusing on the wrong things, and felt I knew my purpose, but was too scared to pursue it 100%. It took a day off, and a long hike on Mount Greylock 24 years ago to spark a new path. That hike prompted me to go to grad school…which propelled the move to San Francisco, and my becoming an entrepreneur.

It was time for that kind of re-set, again, 23 years later.

Magic Happens on Mount Greylock

North Adams, Massachusetts is a tad less than three hours from Cambridge, MA, but a world away in terms of culture and kindness.

I chose a place at the bottom of the mountains, with suspension bridges spanning “The Beyond Place”–an Algonquin term for the Hoosic River. Yes. This is a magical part of the world, understated, with a quiet elegance, woods and rocky cliffs and wild streams.

On my actual birthday, Dalton (my dog) and I took on Mount Greylock–famed for being, the inspiration for the white whale in Moby Dick, the school for American witches and wizards (aka Ilvermorny)–if you can’t see it, you’re a muggle ;), and, of course, was an inspiration for Thoreau.

We walked 6 hours up and 4.5 hours down, an entire day of trekking, thinking, and getting clarity.

What a beautiful day, 63 degrees, crisp–the perfect Fall day, the type of day that reminds me of being a student and *knowing* you can change the world. You’re one with nature, the path opens into sunlight, and the slight breeze coasts you forward. Except…Greylock can be fickle/moody, and seems to like throwing all four seasons in the span of a hike at the mere mortals who dare to trek his surface. We experienced nasty vine-whips of wind, cold bouts of shadows and a few moments of actual…trepidation (N.B.: I dislike like 5-foot tall grass). Dalton and I were alone except for the trees and birds, and whatever animals lived beneath the surface. Overall it was peaceful and empowering.

Hiking is my Headspace App

Halfway up the path we sprawled on a rock, gulping water, bathed in a sunbeam which enveloped the trees and leaves on the ground. A red-tailed hawk circled above, and it was silent. I felt as if the entire world belonged to us, and whatever dreams we brewed.

Hiking in general is my Headspace/Calm/Yoga–I feel it is a metaphor for the journey of life. You can choose your path, but whatever way you go, it’s not supposed to be EASY, or simple, or a padded leather seat limo ride. It’s supposed to be full of twists and turns. Perhaps an unexpected stream and wet socks. Yet also, moments of pure bliss. It’s a hike, and you have to be 100% fully present the entire time.

Mount Greylock is how I got the answers I needed. When we arrived at the summit, we could see 90+ miles into budding fall foliage; mountains, rivers, streams, church steeples and red barns, a perfect, clear view. I knew what I needed to do, what my purpose was, and which path I needed to take to be aligned with it. The perfect birthday gift.

Finding the Path: What Do We Want?

Everyone has heard this saying–what would you do if you didn’t need money, and you could pursue anything you want. What is your purpose in life? The one thing that is so entirely you. The answer to that is usually closer to what you’d be happiest doing, but so many dismiss it. We operate out of fear–we think, there is no way we could earn a living doing that, or we tell ourselves it would be too difficult to change direction. There’s a Paulo Coehlo quote from “The Alchemist,” that reads, “When you want something, all the universe conspires in helping you to achieve it.” In my experience, this is true–it’s not woowoo or crazy–it’s when you’re aligned with your passions and your dreams and you pursue them. When people see that, they help. You find others like you, who pursue their purpose.

When you want something, all the universe conspires in helping you to achieve it.

Paulo Coehlo

My Purpose is Wellbeing

Dalton finding his purpose on a suspension bridge.

I love pursuing wellness and all things related to wellbeing, and I’ve actually known this for a long time–it’s what fueled my last startup back in 2008, it’s what fueled me teaching Aerobics through college and in San Francisco at the YMCA. It’s what attracted me to a certain entrepreneur in SF who was always optimizing his health. It’s what has fueled me to be a lifelong vegetarian, and pursue work that gives me freedom with my schedule. Of course, it’s also why I’m building a new wellness startup.

Align Your Actions With Your Purpose

Yeah, I mean it is obvious, right? But the thing is, it wasn’t–not until I was on a rock, taking a breather on the Bellows Pipe trail on Mount Greylock. The past 3 months I worked almost fulltime on consulting clients, and spent my spare time on paperwork for the sale of my company. No significant progress had been made with my new startup idea, because I hadn’t given it any fuel. I was spending all my time feeding the wrong people, places, and pursuits. All of this was deeply misaligned with my goals, and my true passion.

When I returned from my trip, I refused the sale of my company.

I realized I could hire someone to “be me” at the consultancy and I’d be able to step back, or, I’d find the right buyer who appreciated my goals. By walking away from the deal I could focus on the startup. Walking away had an added benefit, too: by leaving behind “partners” who didn’t fully value me, I started valuing myself more. I have become more confident and more determined.

Here I want to give some credit to Z, my cousin and friend, who helped me see the truth, and realize how much time and energy I was spending on things that were not aligned with my goals.

Onwards With Purpose

My muscles were sore, even a few days after I returned from the Berkshires, and my head hurt, too. My journal was filled with Jackson-Pollocky looking scramblings. I was like a cranky 3-year old who didn’t get enough sleep, but was on the plane to Disney World. This is the what happens when you know what you must do, and you decide to pursue it.

2 weeks ago I hiked that mountain and turned down the deal…and I feel alive. I haven’t figured everything out yet–but I see a path opening up before me. Friends and helpful people are showing up to propel me forward, and I am more content and driven.

Sometimes all we need is to step back and gain some perspective, and sometimes, we need 11 hours on a mountain full of magic.

In the past 2 weeks more progress has been made on the startup than in the prior 3 months. I’ll announce THAT soon. Onwards!

how to take a vacation as a small business owner

5 Steps For Taking Vacations As A Small Business Owner

Taking Vacations = Critical For Your Success!

Taking vacations as small business owner might seem truly daunting. 5 simple, tried-and-true steps can ensure you, too, can take the time off you need.

I just returned from a week in Puerto Rico–a full week without a laptop, cell phone, or client meetings. I’m able to take time off (and really, truly unplug), without risking my business several times a year, and I consider taking time off the single greatest benefit of being a small business owner. The reason I can make it happen? 5 steps that I adhere to.

According to a survey by Harris Interactive, “some 61 percent of Americans plan to work on vacation each year… Among small-business owners who said they do plan to take a vacation this year, the majority—66 percent—will take only one week off all summer long. These owners take on all or most of the responsibility of running their businesses, according to Joe Robinson, a work/life coach, and worry that their businesses will suffer if they’re away from their work for an extended period of time.”

But, guess what? You can take a vacation–even if right now you think you can’t. Not only can you take time off, but you can earn money while you are on vacation, improve your health, and improve the vitality of your business as well. I understand that in today’s world it seems impossible, but it truly isn’t.

Here are the 5 steps to make it happen.

Step 1:Prioritize Time Off

The single most important step for small business owners wanting to take time off, is to prioritize it. Sounds simple, but just like anything in your business, if something isn’t on your “to-do” list, chances are, it’s not going to happen. When you tell yourself that vacations are critical for your own health, and therefore the health of your business, they become justifiable. When we make anything a priority in our life, we find the time. It’s like anything in life, whether it is exercise or getting enough sleep.

If you need some justification in order to prioritize time off, here’s a few good reasons. Time off is known to:

  • Reduce stress
  • Stave off a heart attack
  • Refresh your creativity
  • Increase productivity when you return

In an ABC News article, clinical psychologist Francine Lederer observes, “most people have better life perspective and are more motivated to achieve their goals after a vacation.”  Lederer calls the impact of breaks on mental health “profound.”

When you prioritize time off, you will naturally develop relationships with clients who appreciate your need to go away. I work hard to maintain great relationships with my clients, but I have found that working with “workaholics” doesn’t really work for me. A client that doesn’t have the same value system, and can’t appreciate how I am able to do better work for them because of my time off, isn’t a client I want to keep. I understand that when people are first starting a business, this is a luxury. But clear communication, and delivering stellar work will always help you with clients when its time to tell them you won’t be there for a week or two.

Step 2: Build “Passive Income Streams”

If you’re planning to take a vacation this holiday season, you most likely won’t have time prior to develop what I call “Passive Income Streams”. However, you can start preparing for next year’s vacation, and building an ability to take more nights, weekends, or days off throughout the year. so, what are “Passive Income Streams?” They are sources of income that continue to earn money even without your involvement, or, with minimal involvement. You have to create theses sources of income, but once you do, the “maintenance” and time required of you is minimal–and typically you can easily hire someone to manage these sources of income for you.

Here are some examples of this type of income:

  • Ebooks or Digital Content (Paid)
  • Ecommerce Store (DVDS, Products, Goods)
  • Referral and Affiliate Fees For Links/Recommendations

In January I will host a Webinar discussing how to create Passive Income Streams in more detail. As a small business owner, there will always be tasks and services that only you can perform. Yet building these sources of income allow you to make money no matter where you are or what you are doing (sleeping, kayaking, etc!), and they allow you to scale your business.

Step 3: Prepare & Delegate

Delegating to employees or part-time staff/freelancers is key to ensure things run smoothly while you are away. Even if you own a very small business, or a business that is just YOU, I always suggest hiring someone who can handle any phone calls or emails while you are away. The other key to ensuring a great vacation, is to identify all possible situations while you are gone.

I read a great article in the New York Times entitled “How To Take a Real Vacation While Running A Business” last year, and I particularly liked the advice on contingency planning. Planning for the worst-case scenarios while you are away, and having back-up plans for any possible scenario may seem pessimistic, but it can ensure you aren’t disturbed on your vacation. Having a “what if” list, with steps on precisely what to do in any situation can prevent employees or freelancers from contacting you, since they’ll have a guide as to what to do. I’ve found it best to literally list any “out of the world” situation, with a solution and steps as to what to do in order to minimize, or eliminate, any calls while away. That can be as serious as what to do if a client is threatening to fire you, or as mundane/annoying as a toilet clogging in your business.

Some small business owners are afraid to delegate to their staff, out of fear that things won’t go well and they could risk their business. Depending on the business, there’s a lot of truth to “nobody can do it like you do it.” But being clear with your clients, and setting expectations (next step), will ensure things go well.

Step 4: Set Expectations

Giving as much advanced notice prior to taking time off will help set expectations with clients, employees, and business partners. I’ve found that not only do I need to give as much notice as possible as to time off, but I need to be crystal clear with all aspects of the time off. Some helpful tips:

  • “Pad” your vacation time, by saying it starts earlier and ends later than reality. If I’m leaving at 5am on a Wednesday, I tell clients I’m gone from Tuesday at noon on. This way I won’t have any last-minute stress or requests as I’m packing, preparing, and trying to get enough sleep before an early flight! I always give myself at least half a day after I actually return to be back in the office, or see clients. This has helped me ensure I get enough sleep the day after I return, as well as prevent any scheduling disasters if my travel is delayed, bags are delayed, or anything that might cause stress the next day.
  • Work extra hard the month prior to the vacation. I don’t recommend burning yourself out before a vacation–that always leads to two or three “lost” days on the vacation, where you catch up with sleep…or fight an illness! Yet, putting in some extra night and weekend time, or opening up your hours of service a month before leaving can help clients feel catered to. Be sure to deliver great work, and go above and beyond the “call of duty”. You’ll feel better about taking the time off, and your clients will always appreciate the extra effort.
  • Let everyone know that you will not be answering your cell or checking emails unless in an emergency. This is critical, since unfortunately “vacation” to many people equates to working part of the time. I find that in order to achieve the benefits of time off, I truly have to let go of working for the whole time. That’s why delegation is key, and developing contingency plans.
  • Let clients know who is covering you while you are gone. I am always clear with clients in regard to whom is responsible for what in my absence. For example, if something truly cannot wait until I return, I recommend consultants with similar experience who can act on my behalf. I also have freelancers who can handle day-to-day tasks or answer any questions about my rates or services in the event a new client contacts me. My pilates instructor gives the names of several people he trusts while he is away–and its wonderful to know that he’s helping his clients out and ensuring we can get our pilates fix while he’s away. Some small business owners get frightened that by recommending someone else, their clients might like the new person better. I have found that clients are generally eager for your return, and impressed that you are confident enough in your abilities to recommend others in your absence.

If you run a business and have junior staff/coverage, be clear with clients regarding their skillset and years of experience. That way, you are setting the expectations for the work performed and less likely to run into a customer service issue.

You always want to give a client the option to see someone else while you are gone, since that is part of providing stellar service. Don’t leave them hanging!

Step 5: Unplug

One of the greatest ways to increase stress during a vacation is to not fully unplug. In my experience, the whole “checking in” via email or cell phone once a day adds more stress than letting go, unplugging, and truly enjoying time off. What happens if, when “checking in”, a situation comes up that you cannot resolve remotely? Guaranteed stress and frustration, that’s what. And believe in this–the second you check in, your clients and staff know that you’re available, and they will contact you, make requests of you, and have expectations of you. It sounds like a hard line, and it is. I only check my cell and email in emergency situations–and, I’ve got another secret. I have an email that is specifically only for my family, my staff or contractors to contact me if something goes wrong. That email is a complete secret to everyone else. I will check that secret email address a few times while on vacation, because I know if there is an email there, it’s serious and I need to address it.

The hardest part of unplugging can come down to ego and pride. Let’s face it, unless you are responsible for someone’s life (i.e. you are a brain or heart surgeon, a paramedic, a firefighter, etc), the chances that you truly have an emergency in your business that only you can handle, is slim to none. Realizing that the work you do is important, but not life-or-death critical, can help you take things a bit less seriously, delegate what needs to be delegated, and truly take the time away. And believing that unplugging is your key to taking care of yourself–which is the foundation of all your success as a small business owner, is such an important step.