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Summer’s Over: 10 Ways to Get Back to Work After Summer Vacation

It’s September and the air is rife with that back-to-school feeling of fresh starts. Here are ten tips to transition your business from the lazy days of summer to make the grade this fall.

11 min. read

It’s been 24 years since the beginning of September meant back to school for me, but I still get the urge to buy a pencil case and a new notebook every time Labour Day rolls around.

back to school flintstones lunchbox
I had a lunch box just like this waaaaaay back in the ‘70’s. Makes me feel super back-to-school-y just looking at it.

Actually, September usually feels more like the new year to me than January 1st does. I often do more planning and strategic thinking about both my personal and professional lives in September than I do in January.

In the fall I feel an aura of excitement and optimism about the months ahead, as opposed to January when it feels like there are more negative reasons for needing to re-evaluate. (This may also have to do with the weather where I live in Atlantic Canada - September is glorious, while January is gorey)

If you live in the northern hemisphere, you’re coming off what can be the lazy, hazy days of summer. For most businesses, things moved at a slower pace. With both clients and your team members in and out of the office on various vacations and national holidays, deals probably didn’t close as fast, work didn’t get done as quickly, and major decisions were put off.

So now with a fresh, shiny September upon us, it’s time to kick-start a new season of business growth.

Here are a few suggestions on how you can head back to work from vacation and have a successful fall (but I still support keeping that flip flop spirit alive in your heart).

1. Focus on the positive

Whether you’re a business owner or a member of a team, from time to time you can start feeling stale about your job and what you’re doing, especially when you're returning to work from vacation.

Remind yourself why you started the business, or came to work there in the first place. What you wanted to accomplish, what you wanted to build, how you wanted to grow as a person or an entrepreneur.

Think of all the things you love about what you do - selling, interacting with clients, solving problems, innovating, being creative, working with your team - and then figure out how you can do more of that.

Let these positive feelings fuel your activities for the next quarter and use them to inspire positivity among your team.

2. Focus on the negative

I’m a very positive person but I think there’s real value in examining the ‘negative,’ or put a better way, thinking critically.

It bums us out if we receive a bad review of Proposify, but I think that information is invaluable to the development of the product. How else will we know how to make it better? How else will we slow our churn rate if we don’t know where the problem lies?

So in the same way you should examine all the things you love about your business, it’s important to think about what you don’t like. What isn’t working? What’s making you unhappy and maybe holding you, your business, or your team, back?

Is it a process that needs to be tweaked? Do you need to hire someone to take on something you don’t like so you can concentrate on what you’re best at? Do you need to fire that one bad apple on your team that’s bringing everyone and everything down?

Look at what’s NOT good about your situation and then figure out what needs to happen to change it.

3. Focus on your financials

Hopefully you’re already on top of what’s happening with your bottom line but it is September, and it is a fresh, new business season. When you get back to work, it never hurts to revisit your financial goals versus your current status.

September marks the first month of the final quarter of the year so it’s a good time to reevaluate your projections, examine your expenses, and make a plan for how to make this quarter count.

But don’t stop there.The fall is also the time to start planning your financial goals for the next year, looking at what you need to do to get where you want to be. Will you require outside investment? Where will that come from? You need to start preparing and pitching for that now.

4. Give your team a pep talk

Just like your principal started the school year with an assembly, you should hold one with your team. There’s likely not been a week this summer that everyone’s been in the office at the same time so this is a good opportunity to bring people back together and remind them of the game plan ahead.

I like when it happens right after Labour Day but choose the earliest date possible when your whole team will be present and able to meet.

Make sure the tone is positive and motivational. Remind everyone of the great things you’ve accomplished as a team, and get them focused and excited about the goals for the future, both immediate and long term.

Encourage participation - have each department to give an update on what they’ve been up to and what they’ll be working on in the coming months.

This can help those people dragging their heels off vacation feel reinvigorated, and it can be a subtle reminder that it’s time to get back to business and get shit done.

5. Meet with each department

Even you have a small company, each person on your team has different objectives, approaches, challenges, and expectations related to their job.

Chances are you haven’t really connected in the last couple of months so meeting with each department gives you an opportunity to catch up on a micro level and make plans to solve any issues before they get too big (and maybe even share a vacay story or two).

Are they feeling over or under resourced? Is there a skills gap? Maybe they have ideas on how to be more efficient, bring in new clients, or develop a new service.

Taking the time to talk either one-on-one with the department head, or to the whole group keeps you better informed on what’s happening in your business and motivates your team by demonstrating you are engaged and interested.

6. Invest in your business

If your business is going to grow, you need to make an investment. Discover where the needs lie in your company, research what the options are to address the situation, and evaluate the potential return on investment (not to mention what you can afford).

That may be new technology in the office, like a server upgrade. Maybe you invest in an employee by sending them for professional development to gain new skills, or you’re going to finally hire that extra sales rep to help grow new business.

Maybe the investment is in yourself, by getting a mentor or a business coach to help you grow.

There are likely lots of things in your business that could benefit from extra time and money but even if you pick just one to kick off the fall season, you’ll likely reap the results of that investment in the coming year.

7. Reach out and reconnect

I actually find the summer really busy and so do most people I know. My friends with kids are going in twelve directions between summer camps and family trips, every week someone different is out of the office on vacation, there are a multitude of visitors to entertain, and we’re all just trying to squeeze the most out of each fleeting sunny day.

I also have a side hustle renting baby equipment to people travelling to my city and the summer is basically my Christmas season, so juggling that with my full-time gig at Proposify makes this season even more hectic for me.

As much as I love summer, I look forward to going back to work after the holiday when a routine sets back in, everyone’s focused again, and I can reconnect with people.

Just like Johnnie Taylor sang, “It’s September, you’ve been gone all summer long”

When I had my freelance business, I would send out a personal email to each of my clients after Labour Day to touch base. I’d ask about their summer, check in to see how things were going, and I’d try to include a few project suggestions to spark a conversation.

Maybe it was something we had talked about doing a few months ago, or maybe it was something new altogether, but the point was to re-engage and remind them I was ready to rock.

Depending on the nature of our relationship and the work we had done together, some clients I would try to have coffee with for a face-to-face, others I would suggest a planning meeting to schedule out new projects for the coming months. And for others, the email was just a gentle, “Hey, remember me?” after a beer-soaked summer.

Reconnecting with your existing clients, any prospects that might have gone lukewarm over the summer, and your network in general after vacation is a great way to kick-start new business opportunities for the fall.

Everyone will be back in the saddle and ready to do business so the timing is just right to close some new deals.

8. Find your stress buster

Life is stressful. Work is stressful. Even if you love what you do, there can be some difficult days that take a toll on your spirit. And quadruple that stress level if you’re a business owner.

While you can’t always control what happens to you at work or even your personal life, having a plan for how you deal with stress can prevent the dreaded burnout that can leave you ineffective as a leader and a detriment to your business.

Now’s the time to sign up for that recreational basketball league, pottery class, or roller derby team.

Proposify's Customer Happiness Specialist, Sondra
True story: Proposify’s customer happiness specialist, Sondra, is on a roller derby team. That’s her kicking ass in the pink helmet.

Whatever it is, make sure it has nothing to do with work so you get a chance to clear your head and reset a couple of times a week.

9. Eat...better

Notice I used the word ‘better,’ because I feel like there are so many messages yelling at us about how we eat, bossy messages about what we should and shouldn’t eat. Gluten, sugar, fat, carbs, preservatives with 22-letter names. Ugh. Instead of an all-out war on different kinds of food, why don’t we aim for some incremental improvements? Eating a little better, not necessarily the best.

I’m not going to make any judgement about what you may have eaten over the summer but I will tell you I ate enough juicy BBQ hamburgers (with bacon and cheese, natch), hot dogs roasted over a campfire, and Miss Vickie’s potato chips (my weakness) to make a clogged artery sing.

So it’s time to get back on track a bit. And not because of weight, but because of how eating all that stuff makes me feel, especially that during the week when I’m trying to work. Sluggish, cranky, moody, blahhhhhhhhhhhh.

Food is your fuel, you put junk in your tank and it’s not going to perform as well. I know you’re busy - we’re all busy - but find a way to make a least one meal a day a little better, a little more nutritious.

10. Get a good sleep

My mother is such a strong believer in the power of good sleep that back in high school my brother and I would joke that we could hobble into the house with a gushing stab wound and Mum would say, “You need more sleep!”

She was hardcore on set bedtimes and making sure we got an adequate amount of sleep. It drove us crazy when we were teenagers but I totally get it now.

If I don’t get enough sleep, I feel like I’m hungover without the fun party stories to go with it. I can’t function properly, I’m cranky, and I end up eating crap.

I know there’s this whole hustle philosophy around “I’ll sleep when I’m dead,” which to me is right up there in with the absurd competitive game of “I’m the busiest!” We need to sleep to function properly, period. You can cheat your way out of a lot of things but your body’s need for sleep is not one of them.

Aside from my mum, entrepreneurs are also getting behind the sleep revolution, including Amazon’s Jeff Bezos, and The Huffington Post’s co-founder, Arianna Huffington, who wrote a book about it, even going so far to call sleep deprivation the new smoking.

Check out Arianna’s quick TED Talk called “How to succeed? Get more sleep.”


So if you do nothing else on this list as you get back to work after vacation, at the very least make sure you’re getting a good night’s sleep. It can go a long way in affecting your mental and physical health, two things essential to keep you on your toes, and on top of your business. Don’t make me call my mum on you.

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