Guilt-Free Holidays as an Entrepreneur

It’s a seven-day-a-week occupation, being an entrepreneur. You know that you can grow your business with a lot of elbow grease and a big dose of devotion. No wonder you wonder what the secret is to leave that developing enterprise behind for a few days or weeks and go away on holiday!

Here are some tips to help you start wrapping your mind around why taking a holiday can be helpful not only to you personally but also to the growth of your business.

Guilt-Free Holidays by Defining the Objective Beforehand

The first thing you must do as an entrepreneur is figuring out what you want to get out of your holiday. Do you want to spend some time with your family? Do you want to party with friends and co-workers? Do you want to unwind and reflect a bit on your own? Do you want to completely stop working or continue doing some bits and pieces during your holiday? The goal of a holiday doesn’t need to always be the same.

You might define one vacation as aimed towards spending time with family while the next one might be devoted to your own self-development. This is why it’s important to develop a holiday timetable. At the beginning of each year consult your timetable to figure out how many holidays you’ll be taking in the next twelve months.

Write down the location, people involved and duration of those holidays. The contents of your timetable will depend on your reason for taking a holiday, affordability, availability and responsibilities or workload.

Guilt-Free Holidays by Developing Expectations

Once you have determined what your objective is in taking a holiday, begin developing expectations of yourself – the entrepreneur – along with the other people involved in your holiday. Your expectations should be rather more generic than specific. For example, perhaps lower expectations about modifying the production line as soon as possible, and raise your expectation about your business, say, developing products more strategically.

If your family demands the lion’s share of your time during a holiday (and they most probably will!), you might decide to completely distance yourself from your business. To disappear completely off the face of the business world, you must put some preparatory measures in place.

How Entrepreneurs Can Take Guilt-Free Holidays & Recharge
Appoint a loyal, trustworthy and highly experienced person from your business to carry out your role in the organisation while you are absent. Select a second similarly qualified individual as a proxy to keep the train on the track in case your appointed person encounters an unavoidable circumstance and suddenly becomes unavailable. Create a reliable contact procedure specific to the appointed individual so that he or she can reach you if an extreme emergency arises during your absence.

If your holiday is not family-centric and includes friends and colleagues or just yourself, then you’ll probably not need to spend your entire time vacationing. In such cases, you might either want to work for a few hours or work for a couple of days, alternating with days completely off.

This is an ideal solution for workaholics who start to feel tense when they are away from work. These techniques will help you continue working while simultaneously enjoying some holiday time.

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Guilt-Free Holidays during Slow Business Seasons

Slow business seasons seem like a drag while working, but these are the perfect times for an entrepreneur like you to go on holiday. The workplace won’t be too hectic so everything will function fine without you. For instance, if you run an event management programme, your business probably won’t be too booked full of events in the period after Christmas and New Year. Besides, don’t those slow business days spent in the office feel like a waste of your precious chill-out time anyways?

What if you own a women’s clothing business? Your business is hopping year-round, right? Well, don’t worry, because you can slow actually down your own business for a period by reacting rather than pursuing. This means that you concentrate on filling incoming orders rather than advertising, marketing and soliciting new orders for your company’s goods or services.

Guilt-Free Holidays with Cost-Free Holidays

If you’re a newbie entrepreneur who has just, you probably have quite a small holiday budget. You probably prefer investing in the expansion of your business rather than going on a holiday anyway. A middle ground for your situation can be found with seminars and conferences in beautiful locations within your region.

You can also socialise at these events, which can also impart a bit of a holiday vibe. In addition, you’ll be able to enhance your business insights, expand your professional network and meet potentially helpful leaders and mentors, and even clients!

If you own a large business with international branches, then you can travel to these locations as needed without wasting a single penny. In this way, you’ll be able to inspect the progress of your affiliates. You’ll also get the chance to socialise with your business partners, clients or branch employees while exploring exotic locations.

Guilt-Free Holidays that Help Spark an Idea

Do you feel like you’re out of new ideas in terms of growing your business? Remember that an overworked brain can become too dulled to be creative. This is why you need an eye-opening holiday, preferably a trip around the world. This will give you the opportunity to closely observe everything around you. Pay attention to how businesses like restaurants, transportation, hotels, airlines and tourism services operate.

Focus on their strengths, weaknesses, opportunities and threats. This may spark an idea for a new product that your business can develop. You might even decide to develop a modification of a product that you observe people tend to grumble about.

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Founder @ The New Savvy
Anna Haotanto is the Advisor (former CEO) of The New Savvy. She is currently the COO of ABZD Capital and the CMO of Gourmet Food Holdings, an investment firm focusing on opportunities in the global F&B industry. She is part of the founding committee of the Singapore FinTech Association and heads the Women In FinTech and Partnership Committee. Anna is the President of the Singapore Management University Women Alumni. Anna invests and sits on the board of a few startups. Anna is also part of the Singapore Chinese Chamber of Commerce & Industry Career Women’s Group executive committee. Anna’s story is featured on Millionaire Minds on Channel NewsAsia. She hosts TV shows and events, namely for Channel NewsAsia’s “The Millennial Investor” and “Challenge Tomorrow”, a FinTech documentary. Anna was awarded “Her Times Youth Award” at the Rising50 Women Empowerment Gala, organised by the Indonesian Embassy of Singapore. The award was presented by His Excellency Ngurah Swajaya. She was also awarded Founder of the Year for ASEAN Rice Bowl Startup Awards. She was also awarded the Women Empowerment Award by the Asian Business & Social Forum. Anna has been awarded LinkedIn Power Profiles for founders (2018, 2017), Tatler Gen T, The Peak’s Trailblazers under 40 and a nominee for the Women of The Future award by Aviva


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