Build a business that fits your life

We are all born optimists when it comes to how much we can get done in a day and then end up frustrated and on the road to burnout when we can’t cross off every item on that overly-ambitious to-do list. We beat ourselves up when we end up rolling project delivery dates forward — or maybe have only a passing acquaintance with sleep trying to get it all done.

But this isn’t the lifestyle dream you had when you started your business, is it?

I bet you envisioned:

  • Days working with happy clients and customers, doing what it is you do best
  • Freedom in your schedule to be able to take care of yourself, your friends, and your family
  • Money flowing in because you are great at what you do

Here’s the thing. Creating that life requires a plan.

This small business planning retreat is for you if…

woman sitting on floor with computer

You are a small business owner that doesn’t want to be a part of the hustle culture. Regardless of the hours per week you can or want to devote to your business, this virtual planning retreat will help you make the most of the time you have.

The planning principles I teach are universal — independent of the size or type of business you have.

If you are a small business owner looking for more ease — or sossego as the Brazilians call it — this is the planning retreat for you. We’re going to work hard, but also have some fun along the way.

Audacious goals welcome

Do not confuse building a business that supports your life with “thinking small” or scaling back on your dreams.

That is not what this is about. At all.

If anything, this laser-like focus on doing only what’s necessary will help you grow your business faster and you’ll go further than you could have ever imagined.

Why this counter-intuitive concept works:

  • A happier, more relaxed entrepreneur makes better business decisions
  • You’ll be rid of those business activities that don’t serve you or your business
  • With clear targets and goals, it’s easier to know exactly what needs to be done to get there
  • You will spend more time working in the areas that are your strengths
  • Solid systems and processes mean getting more done in less time
  • And oftentimes, when you’re working on the right things you want to work more because you’re having fun!
I feel like making dreams come true

Planning retreat dates and location

A 2.5-day intensive + quarterly planning days

2.5-day planning intensive dates

Dates: Wednesday – Friday, December 8-10, 2021

Times: 9am – 4pm PT (Friday will break early)

Schedule includes ample breaks

Quarterly planning dates

  • March 11, 2022
  • June 17, 2022
  • September 16, 2022
  • Year-end celebration: December 16, 2022
coffee cup and online retreat

This virtual planning retreat will be held online, via Zoom

Brazil outline

While we will be working and celebrating together from a distance, this retreat has been designed to be as immersive as possible — virtually transporting you to Salvador, Brazil. I’ve designed a Brazil-inspired physical and digital care package to appeal to all of the senses, created an extensive preparation guide, and more.

Meet Jen, your planning retreat hostess and leader

As a former events manager for one of the world’s largest companies, I’ve seen firsthand the transformational power of a well-executed virtual event. The gift of time away — even virtually — leads to business-altering insights. An incredible amount of work can get done in just a few focused days.

Jen Santos

Jen Santos

Founder and Chief Enchantment Officer
Retreat Facilitator



As a coach and consultant for more than 25 years, I have dedicated my entire career to helping others reach their goals. As your retreat facilitator, I’ll guide you through proven planning frameworks to size your business to you and your needs.

I draw heavily on both current program and project management best practices as well as the latest science around happiness, habit, and flow. You need the plan plus the mindset to execute on it.

I’ve been a solopreneur myself for the better part of two decades, coaching and consulting with solopreneurs and small businesses as well as global tech behemoths. My industry experience spans retail, global tech, banking, medical devices, fitness education, and more.

I live in perpetually-sunny Salvador, Brazil with my Brazilian husband, doing everything I can to absorb as much as I can of the rich culture and work-to-live lifestyle. I can’t wait to virtually introduce you to some of it!

A wealth of knowledge

You are a wealth of knowledge, determination, and pure, simple brilliance. You’ve taught me so much — how to weed through the complexity without forgetting the larger picture, the need to set boundaries to maintain sanity, to never stop looking at each element from all sides.

A team member

Making the magic happen: what you can expect

You’ll leave with a realistic business plan for 2022 that supports your personal and professional goals — putting you in the driver’s seat.

Here’s how we’ll get there:

  • Evaluation of your annual and quarterly goals. Are they realistic? Are they moving your business forward?
  • Pruning of your daily activities to just the essentials that are going to make a difference
  • A Brazil-inspired care package delivered to your door to further enhance the retreat experience
  • Discussion of organizational and productivity hacks to up-level your business in an easeful way
  • Small cohort of peers to cheer you on — and keep you accountable — every step of the way
  • Pre-retreat homework and planning guidance so you can fully immerse yourself in the retreat experience
  • Insights into simple things you can do throughout the day to create more spaciousness and develop more ease
  • Digital collaboration tools for brainstorming, ideation, and planning
  • Feedback from other retreat participants so you can immediately vet ideas and get advice
  • Plenty of heads-down, guided planning time so you can plan your year and upcoming quarters
  • Three bonus quarterly check-ins to keep you on track after the intensive is over
  • Visual, auditory, and kinesthetic exercises and activities to support learners of all types
  • Detailed worksheets and templates that you can refer back to time and time again
  • Explore what behavioral science says about overwhelm, happiness, and that mythical work-life balance
  • A year-end celebration of all that we’ve accomplished — personally and professionally

See the detailed agenda

Invest in yourself and sign up today

Make 2022 your biggest, best, happiest, and most relaxed year in business

Co-workers doing a high five

Investment: $1,497 USD. $997 USD.

  • 2.5-day planning intensive to create a plan that works
  • Three follow-up quarterly planning sessions
  • Pre-retreat planning and preparation guide
  • Templates and worksheets to help you every step along the way
  • Coaching, guidance, and a community of peers



A skilled problem-solver and patient teacher

You have a gift for never making others feel stupid for not understanding something or for asking “dumb” questions.

A team member

I’ve always been so inspired by your ability to think clearly and problem solve in the most chaotic of situations and maintain your patience, kindness, and amazing humor while doing so.

A team member

Our virtual planning retreat agenda

From pre-retreat homework and a planning guide all the way through the year-end celebration, see exactly what we’ll be doing in our time together.

Pre-retreat preparation

We’ll get this planning party off on the right foot with a few pre-retreat activities to set you up for success during our three-day intensive:

  • Discover your personal strengths
  • Gather your business basics for the upcoming assessments
  • Prepare your environment to maximize productivity and minimize stress

A retreat planning guide and checklist will be sent after sign-up so you know exactly what you will need. 

Day 1 – Establish your baseline

We’ll spend our first day getting clear on our where we are trying to go, because as a mentor of mine once said, “without a target it is difficult to aim.”

  • Identify your future vision for your business and your life. This keeps us grounded on the big picture throughout the course of the workshop and throughout the rest of the year
  • Set specific goals for 2022 — business, life, and financial
  • Complete a four-part assessment process to better understand how the current state of your business and life matches up against your goals
  • Discuss how we can bend time by managing our personal energy banks
  • Explore environmental hacks that we can use to bring more ease and joy into our workday

Day 2 – Get on track

Today is a day of trade-offs and decisions to align our goals with where we at in our business.

  • Prioritize projects, goals, and milestones based upon business impact
  • Learn how you can use a “red team” for better decision-making
  • Refine your 2022 goals — going after only what matters most to your business
  • Discuss what role the famed project management “triple constraint” has on our ability to complete projects
  • Tips and tricks based upon neuroscience to increase energy and decrease stress
  • Explore outsourcing, remote and global teams, and where these ideas fit into your business based upon your strengths and interests

Day 3 – Q1 planning

We’ll dig deep on Q1, making sure you are crystal-clear on priorities and next steps. We’re putting into practice everything we’ve figured out over the past two days. You walk away with a business plan you can execute on as early as Monday!

  • Monthly project-blocking for the first three months of 2022
  • In-depth breakdown of one project, including task breakdown and estimating
  • Learn a premortem technique to help discover obstacles and challenges before they becomes problems
  • How to apply the science of happiness to your daily life
  • Designing your ideal workday and workweek
  • End of retreat celebration

Quarterly preview days

The best laid plans are often disrupted by the vary nature of life. Once a quarter we’ll do a check-in to recalibrate and:

  • Celebrate our accomplishments
  • Ground ourselves again in the principles of sossego and a business that works for you
  • Preview the following quarter, including an detailed breakdown of one priority project
  • Discuss special systems, organizational, and wellbeing topics

Year-end Celebration

Celebrating all that we did and all that we learned. A virtual toast to 2022.

Invest in yourself and sign up today

Make 2022 your biggest, best, happiest, and most relaxed year in business

Co-workers doing a high five

Investment: $1,497 USD. $997 USD.

  • 2.5-day planning intensive to create a plan that works
  • Three follow-up quarterly planning sessions
  • Pre-retreat planning and preparation guide
  • Templates and worksheets to help you every step along the way
  • Coaching, guidance, and a community of peers


Meet your guide and facilitator, Jen Santos

A magician and superstar

You are a superstar, Jen, and we are so much better because of you. 

A happy client

Your problem solving skills are unparalleled.

A team member

What you do is nothing short of magic!

A team member

Frequently asked questions

How does a retreat work if it's virtual?

A well-executed retreat is as much physical location as it is state of mind. While the entire retreat will take place via Zoom, a number of elements have been built into the retreat to pull you out of your day-to-day and make the most of the retreat experience.

Where will the retreat take place?

The entire retreat will take place via Zoom. Links will be sent out in the days leading up to each date or set of dates.

Is there a discount if I bring my team?

Yes. I think this work is even more effective when the whole team is working from the same playbook. Set up a call and we’ll work out pricing. 

What if I can't come all three days?

You can still absolutely sign up, but the days do build on one another. You would still get all of the worksheets and templates, but you’d be missing out on the dedicated time to do the work, the discussion, and opportunities for the hot seat or one-on-one coaching. If you want to talk more about whether this is still right for you, book a short call and we can talk about it.

Will there be one-on-one coaching?

There will be a very limited amount of one-on-one coaching available.

Will there be hot seats?

Yes, a limited number of hot seats will be available. They are totally optional, and an opportunity for you to ask for support, receive feedback, and gather additional perspectives. Highly recommend!

Is there really swag?

Yes there is! 🎉 A Brazil-inspired care package will be mailed to your house and a digital swag package is included as well. While we can’t be together in person, the hope is to make it as retreat-like as possible.

After you sign up, you’ll also receive a packet with additional ideas, tips, and tricks to retreat-ify our time together. 

What should I wear?

You should wear whatever makes you feel like the awesome small business owner that you are. If you want to come in your pajamas, go for it. If full business attire is what makes you feel ready for this retreat, then go for it. I have had (adult) colleagues show up to calls in dragon onesies — there are few limits.

Do you offer refunds?

Once we have shipped your care package and sent the retreat planning guide, no refunds are available. If circumstances have changed and you can no longer attend, set up a call and we’ll talk through options.

Invest in yourself and sign up today

Make 2022 your biggest, best, happiest, and most relaxed year in business

Co-workers doing a high five

Investment: $1,497 USD. $997 USD.

  • 2.5-day planning intensive to create a plan that works
  • Three follow-up quarterly planning sessions
  • Pre-retreat planning and preparation guide
  • Templates and worksheets to help you every step along the way
  • Coaching, guidance, and a community of peers